Product Name

  • Name

    Sitagliptin phosphate monohydrate

  • EINECS 682-492-2
  • CAS No. 654671-77-9
  • Article Data6
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point
  • Formula C16H15F6N5O.H3PO4.H2O
  • Boiling Point 529.9 °C at 760 mmHg
  • Molecular Weight 523.329
  • Flash Point 274.3 °C
  • Transport Information
  • Appearance White or almost white crystalline powder
  • Safety 24/25-26-28-36/37/39
  • Risk Codes 28-38-41-48-62-63
  • Molecular Structure Molecular Structure of 654671-77-9 (Sitagliptin phosphate monohydrate)
  • Hazard Symbols
  • Synonyms 7-[(3R)-3-Amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazine phosphate monohydrate;Sitagliptin phosphate;
  • PSA 173.84000
  • LogP 1.66180

Synthetic route

sitagliptin
486460-32-6

sitagliptin

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
With phosphoric acid In water; isopropyl alcohol at 70 - 80℃; for 2h; Temperature;97.7%
With phosphoric acid; water In isopropyl alcohol at 20 - 75℃;95%
With phosphoric acid; water In isopropyl alcohol at 75℃;
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
764667-65-4

1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: isopropyl alcohol; acetic acid / 18 h / 50 °C
2: sodium tetrahydroborate; formic acid / tetrahydrofuran / -30 °C
3: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr
4: phosphoric acid; water / isopropyl alcohol / 20 - 75 °C
View Scheme
Multi-step reaction with 4 steps
1: isopropyl alcohol; acetic acid / 18 h / 50 °C
2: sodium tetrahydroborate; acetic acid / tetrahydrofuran / 3 h / 20 °C
3: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr
4: phosphoric acid; water / isopropyl alcohol / 20 - 75 °C
View Scheme
Multi-step reaction with 3 steps
1.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux
2.1: (R, S) t-butyl Josiphos / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 1 h / 20 °C
2.2: 13 h / 50 °C / 10343.2 Torr
3.1: phosphoric acid; water / isopropyl alcohol / 2 h / 68 - 75 °C
View Scheme
(R,Z)-3-[(1-phenylethyl)amino]-1-{3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl}-4-(2,4,5-trifluorophenyl)but-2-en-1-one
1169707-29-2

(R,Z)-3-[(1-phenylethyl)amino]-1-{3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl}-4-(2,4,5-trifluorophenyl)but-2-en-1-one

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; formic acid / tetrahydrofuran / -30 °C
2: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr
3: phosphoric acid; water / isopropyl alcohol / 20 - 75 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; acetic acid / tetrahydrofuran / 3 h / 20 °C
2: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr
3: phosphoric acid; water / isopropyl alcohol / 20 - 75 °C
View Scheme
(3R)-3-[[(1R)-1-phenylethyl]amino]-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
1169707-30-5

(3R)-3-[[(1R)-1-phenylethyl]amino]-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid / methanol; water / 14 h / 50 °C / 7500.75 Torr
2: phosphoric acid; water / isopropyl alcohol / 20 - 75 °C
View Scheme
3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid
868071-17-4

3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium hydroxide; dicyclohexyl-carbodiimide / tetrahydrofuran; water; cis-1,2-Dichloroethylene / 3 h / 20 - 22 °C
1.2: 18.5 h / 10 - 20 °C
2.1: lithium hydroxide / tetrahydrofuran; water / 2.33 h / 20 - 25 °C / pH 3
2.2: 3 h / 0 - 5 °C
3.1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C
4.1: sodium hydroxide / water / 1 h / 0 - 5 °C
5.1: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
N-(benzyloxy)-4(R)-[1-methyl-(2,4,5-trifluorophenyl)]-2-oxoazetidine
767352-30-7

N-(benzyloxy)-4(R)-[1-methyl-(2,4,5-trifluorophenyl)]-2-oxoazetidine

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium hydroxide / tetrahydrofuran; water / 2.33 h / 20 - 25 °C / pH 3
1.2: 3 h / 0 - 5 °C
2.1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C
3.1: sodium hydroxide / water / 1 h / 0 - 5 °C
4.1: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
3(R)-3-[(benzyloxy)amino]-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
1361389-75-4

3(R)-3-[(benzyloxy)amino]-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C
2: sodium hydroxide / water / 1 h / 0 - 5 °C
3: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
sitagliptin phosphate

sitagliptin phosphate

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 1 h / 0 - 5 °C
2: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
769195-26-8

4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogen; dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II) / methanol; acetic acid / 70 °C / 3620.13 Torr / Inert atmosphere; Autoclave
2.1: lithium hydroxide; dicyclohexyl-carbodiimide / tetrahydrofuran; water; cis-1,2-Dichloroethylene / 3 h / 20 - 22 °C
2.2: 18.5 h / 10 - 20 °C
3.1: lithium hydroxide / tetrahydrofuran; water / 2.33 h / 20 - 25 °C / pH 3
3.2: 3 h / 0 - 5 °C
4.1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C
5.1: sodium hydroxide / water / 1 h / 0 - 5 °C
6.1: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
(2,4,5-trifluorophenyl)acetic acid
209995-38-0

(2,4,5-trifluorophenyl)acetic acid

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: triethylamine; magnesium chloride / acetonitrile / 30 - 50 °C / Inert atmosphere
1.2: 5.5 h / 30 °C / Inert atmosphere
2.1: hydrogen; dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II) / methanol; acetic acid / 70 °C / 3620.13 Torr / Inert atmosphere; Autoclave
3.1: lithium hydroxide; dicyclohexyl-carbodiimide / tetrahydrofuran; water; cis-1,2-Dichloroethylene / 3 h / 20 - 22 °C
3.2: 18.5 h / 10 - 20 °C
4.1: lithium hydroxide / tetrahydrofuran; water / 2.33 h / 20 - 25 °C / pH 3
4.2: 3 h / 0 - 5 °C
5.1: phosphoric acid / isopropyl alcohol / 16 h / 30 °C
6.1: sodium hydroxide / water / 1 h / 0 - 5 °C
7.1: phosphoric acid; water / water; isopropyl alcohol / 0.25 h
View Scheme
Multi-step reaction with 5 steps
1.1: dmap; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 20 - 40 °C
1.2: 2 - 3 h / 0 - 5 °C
2.1: N,N-dimethyl acetamide / 1 h / 40 - 70 °C
2.2: 3 - 5 h / 20 - 45 °C
3.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux
4.1: (R, S) t-butyl Josiphos / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 1 h / 20 °C
4.2: 13 h / 50 °C / 10343.2 Torr
5.1: phosphoric acid; water / isopropyl alcohol / 2 h / 68 - 75 °C
View Scheme
2,2,2-trifluoro-N’-[(2Z)-piperazin-2-ylidene]acetohydrazide
763105-70-0

2,2,2-trifluoro-N’-[(2Z)-piperazin-2-ylidene]acetohydrazide

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride / methanol; water / 0.75 h / 55 °C
2.1: N,N-dimethyl acetamide / 1 h / 40 - 70 °C
2.2: 3 - 5 h / 20 - 45 °C
3.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux
4.1: (R, S) t-butyl Josiphos / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 1 h / 20 °C
4.2: 13 h / 50 °C / 10343.2 Torr
5.1: phosphoric acid; water / isopropyl alcohol / 2 h / 68 - 75 °C
View Scheme
(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one
767340-03-4

(Z)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: (R, S) t-butyl Josiphos / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 1 h / 20 °C
1.2: 13 h / 50 °C / 10343.2 Torr
2.1: phosphoric acid; water / isopropyl alcohol / 2 h / 68 - 75 °C
View Scheme
C15H13F3O4

C15H13F3O4

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N,N-dimethyl acetamide / 1 h / 40 - 70 °C
1.2: 3 - 5 h / 20 - 45 °C
2.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux
3.1: (R, S) t-butyl Josiphos / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 1 h / 20 °C
3.2: 13 h / 50 °C / 10343.2 Torr
4.1: phosphoric acid; water / isopropyl alcohol / 2 h / 68 - 75 °C
View Scheme
3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride
762240-92-6

3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N,N-dimethyl acetamide / 1 h / 40 - 70 °C
1.2: 3 - 5 h / 20 - 45 °C
2.1: ammonium acetate; ammonia / methanol; water / 2 h / 30 °C / Heating / reflux
3.1: (R, S) t-butyl Josiphos / chloro(1,5-cyclooctadiene)rhodium(I) dimer / methanol / 1 h / 20 °C
3.2: 13 h / 50 °C / 10343.2 Torr
4.1: phosphoric acid; water / isopropyl alcohol / 2 h / 68 - 75 °C
View Scheme
(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid
486460-00-8

(3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 24 h / 0 °C
2: hydrogenchloride / methanol / 3 h / 20 °C
3: phosphoric acid / isopropyl alcohol; water / Reflux
View Scheme
(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid
936630-57-8

(R)-3-amino-4-phenyl(2,4,5-trifluorophenyl)butanoic acid

sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 10 h / 20 °C
2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 24 h / 0 °C
3: hydrogenchloride / methanol / 3 h / 20 °C
4: phosphoric acid / isopropyl alcohol; water / Reflux
View Scheme
sitagliptin phosphate monohydrate
654671-77-9

sitagliptin phosphate monohydrate

sitagliptin phosphate

sitagliptin phosphate

Conditions
ConditionsYield
In water Purification / work up;
at 58 - 140℃; for 1 - 8h;

Sitagliptin phosphate monohydrate Chemical Properties

IUPAC name: (3R)-3-Amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one ; phosphoric acid ; hydrate
Synonyms: 7-((3R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4- triazolo(4,3-
a)pyrazine monophosphate monohydrate ; Sitagliptin phosphate hydrate
Molecular Formula: C16H20F6N5O6P
Molecular Weight: 523.32408 g/mol
Flash Point: 274.3 °C
Enthalpy of Vaporization: 80.51 kJ/mol
Boiling Point: 529.9 °C at 760 mmHg
Vapour Pressure: 2.59E-11 mmHg at 25 °C
Following is the Structure of Sitagliptin phosphate monohydrate (CAS NO.654671-77-9):
        

Sitagliptin phosphate monohydrate History

 Sitagliptin phosphate monohydrate (CAS NO.654671-77-9) was approved by the U.S. Food and Drug Administration (FDA) on October 17, 2006 and is marketed in the US as Januvia by Merck & Co. On April 2, 2007, the FDA approved an oral combination of sitagliptin and metformin marketed in the US as Janumet.

Sitagliptin phosphate monohydrate Uses

1、Sitagliptin phosphate monohydrate  (CAS NO.654671-77-9) works to competitively inhibit the enzyme dipeptidyl peptidase 4 (DPP-4). This enzyme breaks down the incretins GLP-1 and GIP, gastrointestinal hormones that are released in response to a meal.
2、Sitagliptin phosphate monohydrate also has an effect on appetite. By slowing down gastric motility it induces a feeling of satiety. This reduction of appetite can help patients to lose weight, a useful effect in patients with diabetes.

Sitagliptin phosphate monohydrate Specification

In clinical trials, adverse effects were as common with sitagliptin (whether used alone or with metformin or pioglitazone) as they were with placebo, except for extremely rare nausea and common cold-like symptoms.There is no significant difference in the occurrence of hypoglycemia between placebo and sitagliptin .

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