Product Name

  • Name

    elagolix

  • EINECS
  • CAS No. 834153-87-6
  • Article Data9
  • CAS DataBase
  • Density 1.350
  • Solubility
  • Melting Point
  • Formula C32H30 F5 N3 O5
  • Boiling Point 728.6±70.0 °C(Predicted)
  • Molecular Weight 631.599
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 834153-87-6 (elagolix)
  • Hazard Symbols
  • Synonyms Elagolix;NBI 56418;
  • PSA 102.56000
  • LogP 5.92590

Synthetic route

4-((R)-2-[5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-trifluoromethylbenzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidine-1-yl]-1-phenylethylamino)butyric acid ethyl ester
832720-84-0

4-((R)-2-[5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-trifluoromethylbenzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidine-1-yl]-1-phenylethylamino)butyric acid ethyl ester

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Stage #1: ethyl (R)-4-((2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-1-phenylethyl)amino)butanoate With sodium hydroxide; water In ethanol at 35℃; for 2h;
Stage #2: With hydrogenchloride In water at 10 - 22℃; for 17h; pH=6.1;		91%
With water; sodium hydroxide In ethanol at 35℃;86%
With water; sodium hydroxide In ethanol at 50℃; for 2h;83.59%
(R)-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-3-[2-(2-oxopyrrolidin-1-yl)-2-phenylethyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

(R)-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-3-[2-(2-oxopyrrolidin-1-yl)-2-phenylethyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 55 - 60℃;89%
ethyl (R)-4-((tert-butoxycarbonyl)(2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1-(2H)-yl)-1-phenylethyl)amino)butyrate

ethyl (R)-4-((tert-butoxycarbonyl)(2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1-(2H)-yl)-1-phenylethyl)amino)butyrate

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
With water; potassium carbonate In tetrahydrofuran at 50℃; for 6h; Solvent; Temperature;82%
3-[(2R)-amino-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-2,4(1H,3H)-pyrimidinedione trifluoroacetate
830346-50-4

3-[(2R)-amino-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-2,4(1H,3H)-pyrimidinedione trifluoroacetate

Succinic semialdehyde
692-29-5

Succinic semialdehyde

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 25℃; for 18h; Reagent/catalyst; Solvent; Temperature;65%
methyl (R)-4-{2-[5-(2-fluoro-3-methoxyphenyl)-3-[2-fluoro-6-(trifluoromethyl)benzyl]-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenylethylamino}butyrate
1092070-97-7

methyl (R)-4-{2-[5-(2-fluoro-3-methoxyphenyl)-3-[2-fluoro-6-(trifluoromethyl)benzyl]-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenylethylamino}butyrate

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
With water; lithium hydroxide In methanol at 45℃;
3-[(2R)-amino-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-2,4(1H,3H)-pyrimidinedione trifluoroacetate
830346-50-4

3-[(2R)-amino-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-2,4(1H,3H)-pyrimidinedione trifluoroacetate

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
2: sodium hydroxide; water / ethanol / 35 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
2: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
2: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
5-(2-fluoro-3-methoxyphenyl)-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methylpyrimidine-2,4(1H,3H)-dione
1150560-59-0

5-(2-fluoro-3-methoxyphenyl)-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methylpyrimidine-2,4(1H,3H)-dione

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 55 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
3: sodium hydroxide; water / ethanol / 35 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
3: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
3: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione
1150560-54-5

1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide; tri tert-butylphosphoniumtetrafluoroborate / acetone; water / 0.83 h / 15 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 55 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
4: sodium hydroxide; water / ethanol / 35 °C
View Scheme
(2-fluoro-3-methoxyphenyl)boronic acid
352303-67-4

(2-fluoro-3-methoxyphenyl)boronic acid

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide; tri tert-butylphosphoniumtetrafluoroborate / acetone; water / 0.83 h / 15 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 55 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
4: sodium hydroxide; water / ethanol / 35 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanol; water / 24 h / 70 °C
2.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
2.2: 1 h / 80 °C / Inert atmosphere
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
4.1: toluene / 4 h / Reflux
4.2: 2 h / Reflux
5.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
7.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanol; water / 24 h / 70 °C
2.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
2.2: 1 h / 80 °C / Inert atmosphere
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
4.1: toluene / 4 h / Reflux
4.2: 2 h / Reflux
5.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
7.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanol; water / 24 h / 70 °C
2.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
2.2: 1 h / 80 °C / Inert atmosphere
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
4.1: toluene / 4 h / Reflux
4.2: 2 h / Reflux
5.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
7.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanol; water / 24 h / 70 °C
2.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
2.2: 1 h / 80 °C / Inert atmosphere
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
4.1: toluene / 4 h / Reflux
4.2: 2 h / Reflux
5.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
7.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
(S)-(+)-<2-<(methylsulfonyl)oxy>-1-phenylethyl>carbamic acid 1,1-dimethylethyl ester
110143-62-9

(S)-(+)-<2-<(methylsulfonyl)oxy>-1-phenylethyl>carbamic acid 1,1-dimethylethyl ester

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 55 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
3: sodium hydroxide; water / ethanol / 35 °C
View Scheme
(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid
2900-27-8

(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 10 °C
2: potassium carbonate / N,N-dimethyl-formamide / 55 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 52 °C
4: sodium hydroxide; water / ethanol / 35 °C
View Scheme
2-(2-fluoro-3-methoxyphenyl)-3-oxo-butyric acid ethyl ester

2-(2-fluoro-3-methoxyphenyl)-3-oxo-butyric acid ethyl ester

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene / 105 - 110 °C
1.2: 105 - 110 °C
2.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 - 100 °C
3.1: sodium hydroxide; water / ethanol / 55 - 60 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
5-bromo-6-methyluracil
15018-56-1

5-bromo-6-methyluracil

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / N,N-dimethyl-formamide / 75 - 85 °C
2: iron(III)-acetylacetonate; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 0 - 45 °C
3: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 - 100 °C
4: sodium hydroxide; water / ethanol / 55 - 60 °C
View Scheme
1-(bromomethyl)-2-fluoro-6-(trifluoromethyl)benzene
239087-08-2

1-(bromomethyl)-2-fluoro-6-(trifluoromethyl)benzene

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / N,N-dimethyl-formamide / 75 - 85 °C
2: iron(III)-acetylacetonate; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 0 - 45 °C
3: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 - 100 °C
4: sodium hydroxide; water / ethanol / 55 - 60 °C
View Scheme
5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione
830346-48-0

5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4-(1H,3H)-dione

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: iron(III)-acetylacetonate; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 0 - 45 °C
2: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 - 100 °C
3: sodium hydroxide; water / ethanol / 55 - 60 °C
View Scheme
1-bromo-2-fluoro-3-methoxybenzene
295376-21-5

1-bromo-2-fluoro-3-methoxybenzene

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate; L-proline; copper(l) iodide / dimethyl sulfoxide / 45 - 50 °C / Inert atmosphere
2.1: toluene / 105 - 110 °C
2.2: 105 - 110 °C
3.1: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 90 - 100 °C
4.1: sodium hydroxide; water / ethanol / 55 - 60 °C
View Scheme
2-(2-fluoro-3-methoxyphenyl)-3-oxo-butyric acid tert-butyl ester

2-(2-fluoro-3-methoxyphenyl)-3-oxo-butyric acid tert-butyl ester

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
2-(2-fluoro-3-methoxyphenyl)-3-oxo-butyric acid benzyl ester

2-(2-fluoro-3-methoxyphenyl)-3-oxo-butyric acid benzyl ester

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
2-(2-fluoro-3-methoxyphenyl)-3-oxo-butyric acid methyl ester

2-(2-fluoro-3-methoxyphenyl)-3-oxo-butyric acid methyl ester

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
(2-fluoro-6-(trifluoromethyl) phenyl)methanamine
239087-06-0

(2-fluoro-6-(trifluoromethyl) phenyl)methanamine

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 3 h / Reflux
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 3 h / Reflux
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 3 h / Reflux
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
2-fluoro-6-(trifluoromethyl)benzaldehyde
60611-24-7

2-fluoro-6-(trifluoromethyl)benzaldehyde

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydroxylamine hydrochloride; sodium hydroxide / water; ethanol / 1 h
1.2: 2 h
2.1: hydrogenchloride / water / 3 h / Reflux
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 6 steps
1.1: hydroxylamine hydrochloride; sodium hydroxide / water; ethanol / 1 h
1.2: 2 h
2.1: hydrogenchloride / water / 3 h / Reflux
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 6 steps
1.1: hydroxylamine hydrochloride; sodium hydroxide / water; ethanol / 1 h
1.2: 2 h
2.1: hydrogenchloride / water / 3 h / Reflux
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
N-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}urea
830346-46-8

N-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}urea

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 4 h / Reflux
1.2: 2 h / Reflux
2.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
4.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
potassium 2-fluoro-3-methoxy-phenyl-1-trifluoroborate

potassium 2-fluoro-3-methoxy-phenyl-1-trifluoroborate

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
1.2: 1 h / 80 °C / Inert atmosphere
2.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 6 steps
1.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
1.2: 1 h / 80 °C / Inert atmosphere
2.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 6 steps
1.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
1.2: 1 h / 80 °C / Inert atmosphere
2.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 6 steps
1.1: tetra(n-butyl)ammonium hydroxide / water / 0.03 h / Inert atmosphere
1.2: 1 h / 80 °C / Inert atmosphere
2.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
5-(2-fluoro-3-methoxyphenyl)-2,2,6-trimethyl-4H-1,3-dioxin-4-one

5-(2-fluoro-3-methoxyphenyl)-2,2,6-trimethyl-4H-1,3-dioxin-4-one

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
2-fluoro-1-iodo-3-methoxybenzene
1080673-30-8

2-fluoro-1-iodo-3-methoxybenzene

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: copper(l) iodide; 4R-4-hydroxyproline; caesium carbonate / dimethyl sulfoxide / 96 h / 60 °C / Heating
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: copper(l) iodide; 4R-4-hydroxyproline; caesium carbonate / dimethyl sulfoxide / 96 h / 60 °C / Heating
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: copper(l) iodide; 4R-4-hydroxyproline; caesium carbonate / dimethyl sulfoxide / 96 h / 60 °C / Heating
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: copper(l) iodide; 4R-4-hydroxyproline; caesium carbonate / dimethyl sulfoxide / 96 h / 60 °C / Heating
2.1: toluene / 4 h / Reflux
2.2: 2 h / Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
5.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
1-fluoro-2-methoxybenzene
321-28-8

1-fluoro-2-methoxybenzene

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N,N,N',N'',N'''-pentamethyldiethylenetriamine; n-butyllithium / tetrahydrofuran / 1 h / -78 °C
1.2: 2 h / -78 °C
2.1: copper(l) iodide; 4R-4-hydroxyproline; caesium carbonate / dimethyl sulfoxide / 96 h / 60 °C / Heating
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 6 steps
1.1: N,N,N',N'',N'''-pentamethyldiethylenetriamine; n-butyllithium / tetrahydrofuran / 1 h / -78 °C
1.2: 2 h / -78 °C
2.1: copper(l) iodide; 4R-4-hydroxyproline; caesium carbonate / dimethyl sulfoxide / 96 h / 60 °C / Heating
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 6 steps
1.1: N,N,N',N'',N'''-pentamethyldiethylenetriamine; n-butyllithium / tetrahydrofuran / 1 h / -78 °C
1.2: 2 h / -78 °C
2.1: copper(l) iodide; 4R-4-hydroxyproline; caesium carbonate / dimethyl sulfoxide / 96 h / 60 °C / Heating
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 6 steps
1.1: N,N,N',N'',N'''-pentamethyldiethylenetriamine; n-butyllithium / tetrahydrofuran / 1 h / -78 °C
1.2: 2 h / -78 °C
2.1: copper(l) iodide; 4R-4-hydroxyproline; caesium carbonate / dimethyl sulfoxide / 96 h / 60 °C / Heating
3.1: toluene / 4 h / Reflux
3.2: 2 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 100 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 2 h / 50 °C
View Scheme
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

elagolix phosphoric acid salt

elagolix phosphoric acid salt

Conditions
ConditionsYield
With phosphoric acid In ethyl acetate at 0 - 10℃;93.6%
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 1 h / 60 °C
2: phosphoric acid / water / 25 °C
View Scheme
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

(R)-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-3-[2-(2-oxopyrrolidin-1-yl)-2-phenylethyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

(R)-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-3-[2-(2-oxopyrrolidin-1-yl)-2-phenylethyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Conditions
ConditionsYield
With dmap; di-tert-butyl dicarbonate In acetonitrile92%
Stage #1: 4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid With triethylamine In dichloromethane at 20℃; for 1h;
Stage #2: With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 24h;		64.8%
In butanone at 25℃; for 168h;93.03 %Chromat.
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 1 h / 60 °C
2: butanone / 168 h / 25 °C
View Scheme
formaldehyd
50-00-0

formaldehyd

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

(R)-4-{2-[5-(2-fluoro-3-methoxyphenyl)-3-[2-fluoro-6-(trifluoromethyl)benzyl]-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenylethyl-N-methylamino}butyric acid

(R)-4-{2-[5-(2-fluoro-3-methoxyphenyl)-3-[2-fluoro-6-(trifluoromethyl)benzyl]-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenylethyl-N-methylamino}butyric acid

Conditions
ConditionsYield
With borane pyridine complex In methanol at 20℃;
With borane pyridine In methanol
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

sodium 4-({(1R)-2-[5-(2-fluoro-3-methoxyphenyl)-3-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl]-1-phenylethyl}amino)butanoate

sodium 4-({(1R)-2-[5-(2-fluoro-3-methoxyphenyl)-3-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl]-1-phenylethyl}amino)butanoate

Conditions
ConditionsYield
With Dowex MSC-11.58 g
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

sodium 3-[2(R)-{hydroxycarbonylpropylamino}-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-((2H3)-methyl)-3H-pyrimidine-2,4-dione

sodium 3-[2(R)-{hydroxycarbonylpropylamino}-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-((2H3)-methyl)-3H-pyrimidine-2,4-dione

Conditions
ConditionsYield
With water-d2; sodium carbonate for 15h; Reflux;
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

3-[2(R)-{hydroxycarbonylpropylamino}-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-((2H3)-methyl)-3H-pyrimidine-2,4-dione

3-[2(R)-{hydroxycarbonylpropylamino}-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-((2H3)-methyl)-3H-pyrimidine-2,4-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate; water-d2 / 15 h / Reflux
2: sodium carbonate; water-d2 / 15 h / Reflux
View Scheme
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

elagolix hydrochloride

elagolix hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 1 h / 60 °C
2: hydrogenchloride / water / 25 °C
View Scheme
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

elagolix hydrobromide

elagolix hydrobromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 1 h / 60 °C
2: hydrogen bromide / water / 25 °C
View Scheme
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

elagolix nitrate

elagolix nitrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 1 h / 60 °C
2: nitric acid / water / 25 °C
View Scheme
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

elagolix, sulfuric acid salt

elagolix, sulfuric acid salt

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 1 h / 60 °C
2: sulfuric acid / water / 25 °C
View Scheme
With sulfuric acid In acetonitrile at 27℃; Solvent; Temperature;
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

C32H29F5N3O5(1-)*K(1+)

C32H29F5N3O5(1-)*K(1+)

Conditions
ConditionsYield
With potassium hydroxide In water at 60℃; for 1h;3.7 g
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

2C32H29F5N3O5(1-)*Ca(2+)

2C32H29F5N3O5(1-)*Ca(2+)

Conditions
ConditionsYield
With calcium acetate In water at 60℃; for 1h;3.5 g
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

Pamoic acid
130-85-8

Pamoic acid

elagolix pamoic acid salt (1:1)

elagolix pamoic acid salt (1:1)

Conditions
ConditionsYield
In methanol at 25 - 60℃; for 19h;1.5 g
4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid
834153-87-6

4-((R)-2-[5-(2- fluoro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl ]-1- phenylethylamino)-butyric acid

benzenesulfonic acid
98-11-3

benzenesulfonic acid

elagolix benzenesulfonic acid salt

elagolix benzenesulfonic acid salt

Conditions
ConditionsYield
In methanol at 20 - 60℃; for 26h;1.1 g

Elagolix Specification

Elagolix , with the CAS register number 834153-87-6, has the chemical molecular formular C32H30F5N3O5. And it can also be called as 4-[[(1R)-2-[5-(2-Fluoro-3-methoxyphenyl)-3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-1-phenylethyl]amino]butanoic acid , and NBI 56418 .

Some characteristics of Elagolix are as below: (1)molecular weight:631.59 ; (2)Density: 1.350 .

Elagolix is a kind of new chemical entity which is being a first-in-class oral gonadotropin-realeasing hormone( GnTh) antagonist. It allows partial estrogen and belongs to the BNF category of posterior pituitary hormones and antagonists (06.05.02). For now, it is being used as the experimental drug in the treatment endometriosis pain. And some reaserch will study this kind of chemical as the curing medicine for the uterine leiomyoma.

As for the market condition of this kind of chemical, it has many suppliers in China, such as Hangzhou Onicon Chemical Co., Ltd., MedKoo Biosciences , and Shanghai Sun-shine Chemical Technology Co., Ltd.
 

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