Product Name

  • Name

    Atrasentan

  • EINECS
  • CAS No. 173937-91-2
  • Article Data8
  • CAS DataBase
  • Density 1.188 g/cm3
  • Solubility
  • Melting Point 122-124°
  • Formula C29H38N2O6
  • Boiling Point 659.4 °C at 760 mmHg
  • Molecular Weight 510.631
  • Flash Point 352.6 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 173937-91-2 (Atrasentan)
  • Hazard Symbols
  • Synonyms ABT 627;ABT-627;Arasentan;(2R,3R,4S)-4-benzo[1,3]dioxol-5-yl-1-(dibutylcarbamoylmethyl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid;(+)-A 127722;3-Pyrrolidinecarboxylic acid, 4-(1,3-benzodioxol-5-yl)-1-(2-dibutylamino)-2-oxoethyl)-2-(4-methoxyphenyl)-, (2R-(2alpha,3beta,4alpha))-;Atrasentan [INN];3-Pyrrolidinecarboxylic acid, 4-(1,3-benzodioxo-5-yl)-1-(2-(dibutylamino)-2-oxoethyl)-2-(4-methoxyphenyl)-, (2R,3R,4S)-;
  • PSA 88.54000
  • LogP 4.63190

Synthetic route

2-[(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-((S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl)-2-(4-methoxy-phenyl)-pyrrolidin-1-yl]-N,N-dibutyl-acetamide

2-[(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-((S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl)-2-(4-methoxy-phenyl)-pyrrolidin-1-yl]-N,N-dibutyl-acetamide

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran for 0.5h;78%
5-((E)-2-nitroethenyl)-1,3-benzodioxole
1485-00-3, 22568-48-5

5-((E)-2-nitroethenyl)-1,3-benzodioxole

palladium

palladium

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 78 percent / DBU / tetrahydrofuran; propan-2-ol / 4 h / Ambient temperature
2: 12.34 g / H2 / Raney nickel / ethanol / 3040 Torr
3: 1.) sodium cyanoborohydride, 2.) bromocresol green, conc. HCl / 1.) THF, EtOH, 2.) THF, EtOH, 20 min
4: 2.775 g / C2H5ONa / ethanol / Heating
5: 91 percent / CH2Cl2 / 1 h / Ambient temperature
6: 95 percent / NaOH
7: 1.) Et3N, t-BuCOCl, 2.) n-BuLi
8: 4 N aq. HCl / dioxane
9: iPr2NEt / acetonitrile
10: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
Multi-step reaction with 9 steps
1: 78 percent / DBU / tetrahydrofuran; propan-2-ol / 4 h / Ambient temperature
2: 12.34 g / H2 / Raney nickel / ethanol / 3040 Torr
3: 1.) sodium cyanoborohydride, 2.) bromocresol green, conc. HCl / 1.) THF, EtOH, 2.) THF, EtOH, 20 min
4: 91 percent / CH2Cl2 / 1 h / Ambient temperature
5: 95 percent / NaOH
6: 1.) Et3N, t-BuCOCl, 2.) n-BuLi
7: 4 N aq. HCl / dioxane
8: iPr2NEt / acetonitrile
9: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
N,N-dibutylbromoacetamide
40124-27-4

N,N-dibutylbromoacetamide

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iPr2NEt / acetonitrile
2: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
dibutylamine
111-92-2

dibutylamine

(+-)-2-chloro-1-<6-methoxy-8-nitro-<4>quinolyl>-ethanol

(+-)-2-chloro-1-<6-methoxy-8-nitro-<4>quinolyl>-ethanol

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / 1,2-dichloro-ethane / 0.83 h / -20 - 20 °C
2: iPr2NEt / acetonitrile
3: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
Ethyl 2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-4.5-dihydro-3H-pyrrole-3-carboxylate
173864-46-5

Ethyl 2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-4.5-dihydro-3H-pyrrole-3-carboxylate

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) sodium cyanoborohydride, 2.) bromocresol green, conc. HCl / 1.) THF, EtOH, 2.) THF, EtOH, 20 min
2: 2.775 g / C2H5ONa / ethanol / Heating
3: 91 percent / CH2Cl2 / 1 h / Ambient temperature
4: 95 percent / NaOH
5: 1.) Et3N, t-BuCOCl, 2.) n-BuLi
6: 4 N aq. HCl / dioxane
7: iPr2NEt / acetonitrile
8: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
Multi-step reaction with 7 steps
1: 1.) sodium cyanoborohydride, 2.) bromocresol green, conc. HCl / 1.) THF, EtOH, 2.) THF, EtOH, 20 min
2: 91 percent / CH2Cl2 / 1 h / Ambient temperature
3: 95 percent / NaOH
4: 1.) Et3N, t-BuCOCl, 2.) n-BuLi
5: 4 N aq. HCl / dioxane
6: iPr2NEt / acetonitrile
7: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
Ethyl 2-(4-methoxybenzoyl)-3-(3,4-methylenedioxy-phenyl)-4-nitro-butanoate
173864-45-4

Ethyl 2-(4-methoxybenzoyl)-3-(3,4-methylenedioxy-phenyl)-4-nitro-butanoate

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 12.34 g / H2 / Raney nickel / ethanol / 3040 Torr
2: 1.) sodium cyanoborohydride, 2.) bromocresol green, conc. HCl / 1.) THF, EtOH, 2.) THF, EtOH, 20 min
3: 2.775 g / C2H5ONa / ethanol / Heating
4: 91 percent / CH2Cl2 / 1 h / Ambient temperature
5: 95 percent / NaOH
6: 1.) Et3N, t-BuCOCl, 2.) n-BuLi
7: 4 N aq. HCl / dioxane
8: iPr2NEt / acetonitrile
9: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
Multi-step reaction with 8 steps
1: 12.34 g / H2 / Raney nickel / ethanol / 3040 Torr
2: 1.) sodium cyanoborohydride, 2.) bromocresol green, conc. HCl / 1.) THF, EtOH, 2.) THF, EtOH, 20 min
3: 91 percent / CH2Cl2 / 1 h / Ambient temperature
4: 95 percent / NaOH
5: 1.) Et3N, t-BuCOCl, 2.) n-BuLi
6: 4 N aq. HCl / dioxane
7: iPr2NEt / acetonitrile
8: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
ethyl 4-(1,3-benzodioxol-5-yl)-N-tert-butoxycarbonyl-2-(4-methoxyphenyl)pyrrolidine-3-carboxylate

ethyl 4-(1,3-benzodioxol-5-yl)-N-tert-butoxycarbonyl-2-(4-methoxyphenyl)pyrrolidine-3-carboxylate

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 95 percent / NaOH
2: 1.) Et3N, t-BuCOCl, 2.) n-BuLi
3: 4 N aq. HCl / dioxane
4: iPr2NEt / acetonitrile
5: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-((S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-((S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 4 N aq. HCl / dioxane
2: iPr2NEt / acetonitrile
3: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
(2R,3S,4S)-4-Benzo[1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

(2R,3S,4S)-4-Benzo[1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 2.775 g / C2H5ONa / ethanol / Heating
2: 91 percent / CH2Cl2 / 1 h / Ambient temperature
3: 95 percent / NaOH
4: 1.) Et3N, t-BuCOCl, 2.) n-BuLi
5: 4 N aq. HCl / dioxane
6: iPr2NEt / acetonitrile
7: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
ethyl c-(1,3-benzodioxol-5-yl)-r-2-(4-methoxyphenyl)pyrrolidine-t-3-carboxylate

ethyl c-(1,3-benzodioxol-5-yl)-r-2-(4-methoxyphenyl)pyrrolidine-t-3-carboxylate

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 91 percent / CH2Cl2 / 1 h / Ambient temperature
2: 95 percent / NaOH
3: 1.) Et3N, t-BuCOCl, 2.) n-BuLi
4: 4 N aq. HCl / dioxane
5: iPr2NEt / acetonitrile
6: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
rac-(2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

rac-(2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) Et3N, t-BuCOCl, 2.) n-BuLi
2: 4 N aq. HCl / dioxane
3: iPr2NEt / acetonitrile
4: 78 percent / aq. LiOH, 30percent aq. H2O2 / tetrahydrofuran / 0.5 h
View Scheme
N,N-dibutylbromoacetamide
40124-27-4

N,N-dibutylbromoacetamide

ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate
178739-03-2

ethyl (2R,3R,4S)-5-(4-methoxyphenyl)-3-(3,4-(methylenedioxy)phenyl)pyrrolidine-3-carboxylate

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile
ethyl (2R,3R,4S)-(+)-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate, (S)-(+)-mandelate
195708-14-6

ethyl (2R,3R,4S)-(+)-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate, (S)-(+)-mandelate

N,N-dibutylbromoacetamide
40124-27-4

N,N-dibutylbromoacetamide

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Stage #1: ethyl (2R,3R,4S)-(+)-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate, (S)-(+)-mandelate With sodium hydrogencarbonate In water; ethyl acetate at 25℃;
Stage #2: N,N-dibutylbromoacetamide With N-ethyl-N,N-diisopropylamine In acetonitrile at 10℃; for 12h;
Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages;
ethyl (2R,3R,4S)-(+)-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate, (S)-(+) mandelate
403614-49-3

ethyl (2R,3R,4S)-(+)-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate, (S)-(+) mandelate

N,N-dibutylbromoacetamide
40124-27-4

N,N-dibutylbromoacetamide

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

atrasentan
173937-91-2

atrasentan

Conditions
ConditionsYield
Stage #1: ethyl (2R,3R,4S)-(+)-2-(4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylate, (S)-(+) mandelate With sodium hydrogencarbonate In water; ethyl acetate at 25℃;
Stage #2: N,N-dibutylbromoacetamide; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile at 110℃; for 16h;
...Expand
atrasentan
173937-91-2

atrasentan

Atrasentan hydrochloride

Atrasentan hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water; ethyl acetate for 0.25h;
With hydrogenchloride In water; ethyl acetate at 0℃; for 2 - 3h; Product distribution / selectivity;
With hydrogenchloride In ethanol; water; ethyl acetate for 0.25h; Product distribution / selectivity;
With hydrogenchloride In ethyl acetate at 0 - 45℃; for 26.5 - 39.5h;
(S)-Mandelic acid
17199-29-0

(S)-Mandelic acid

atrasentan
173937-91-2

atrasentan

atrasentan (S)-mandelate salt

atrasentan (S)-mandelate salt

Conditions
ConditionsYield
In methanol; water at 50℃;
(S)-Mandelic acid
17199-29-0

(S)-Mandelic acid

atrasentan
173937-91-2

atrasentan

atrasentan (S)-mandelate salt

atrasentan (S)-mandelate salt

Conditions
ConditionsYield
In methanol; water at 40℃; Temperature;
(R)-Mandelic Acid
611-71-2

(R)-Mandelic Acid

atrasentan
173937-91-2

atrasentan

atrasentan R-mandelate salt

atrasentan R-mandelate salt

Conditions
ConditionsYield
In water at 50℃; for 0.25h; Sonication;

Atrasentan Specification

This chemical is called Atrasentan, and its systematic name is (2R,3R,4S)-4-(1,3-Benzodioxol-5-yl)-1-[2-(dibutylamino)-2-oxoethyl]-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid. With the molecular formula of C29H38N2O6, its molecular weight is 510.62. The CAS registry number of this chemical is 173937-91-2. Additionally, its classification code is Endothelin-receptor antagonist. It's an experimental drug that is being studied for the treatment of various types of cancer and an endothelin receptor antagonist selective for subtype A (ETA).

Other characteristics of the Atrasentan can be summarised as followings: (1)ACD/LogP: 5.80; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 3.5; (4)ACD/LogD (pH 7.4): 2.8; (5)ACD/BCF (pH 5.5): 75.68; (6)ACD/BCF (pH 7.4): 15.25; (7)ACD/KOC (pH 5.5): 171.52; (8)ACD/KOC (pH 7.4): 34.57; (9)#H bond acceptors: 8; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 77.54 Å2; (13)Index of Refraction: 1.565; (14)Molar Refractivity: 139.98 cm3; (15)Molar Volume: 429.5 cm3; (16)Polarizability: 55.49×10-24cm3; (17)Surface Tension: 47.7 dyne/cm; (18)Density: 1.188 g/cm3; (19)Flash Point: 352.6 °C; (20)Enthalpy of Vaporization: 101.97 kJ/mol; (21)Boiling Point: 659.4 °C at 760 mmHg; (22)Vapour Pressure: 2.76E-18 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: O=C(O)[C@H]4[C@H](c1ccc(OC)cc1)N(CC(=O)N(CCCC)CCCC)C[C@@H]4c2ccc3OCOc3c2
2.InChI: InChI=1/C29H38N2O6/c1-4-6-14-30(15-7-5-2)26(32)18-31-17-23(21-10-13-24-25(16-21)37-19-36-24)27(29(33)34)28(31)20-8-11-22(35-3)12-9-20/h8-13,16,23,27-28H,4-7,14-15,17-19H2,1-3H3,(H,33,34)/t23-,27-,28+/m1/s1
3.InChIKey: MOTJMGVDPWRKOC-QPVYNBJUBX

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