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CAS No.: | 1297538-32-9 |
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Name: | ODM-201 |
Article Data: | 10 |
Molecular Structure: | |
Formula: | C19H19ClN6O2 |
Molecular Weight: | 398.852 |
Synonyms: | ODM-201;BAY-1841788;N-[(1S)-2-[3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl]-1-methylethyl]-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide;Darolutamide |
EINECS: | -0 |
Density: | 1.41±0.1 g/cm3(Predicted) |
Boiling Point: | 719.5±60.0 °C(Predicted) |
PSA: | 119.62000 |
LogP: | 3.06098 |
N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-[(1RS)-1-hydroxyethyl]-1H-pyrazole-3-carboxamide
Conditions | Yield |
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With sodium hydroxide In ethanol; water at 20℃; | 93.3% |
N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-[(1RS)-1-hydroxyethyl]-1H-pyrazole-3-carboxamide
Conditions | Yield |
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With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 6h; | 92.9% |
N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-[(1RS)-1-hydroxyethyl]-1H-pyrazole-3-carboxamide
Conditions | Yield |
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With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 87.5% |
5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide
N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-[(1RS)-1-hydroxyethyl]-1H-pyrazole-3-carboxamide
Conditions | Yield |
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With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; | 85.9% |
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 3.5h; | 80.2% |
With sodium tetrahydroborate; ethanol In ethanol | 76% |
With sodium tetrahydroborate; ethanol | 76% |
(S)-4-(1-(2-aminopropyl) 1H-pyrazol-3-yl)-2-chlorobenzonitrile
C6H8N2O3
N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-[(1RS)-1-hydroxyethyl]-1H-pyrazole-3-carboxamide
Conditions | Yield |
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With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at -10℃; for 2h; Inert atmosphere; | 73.2% |
(S)-3-acetyl-N-(1-(3-(3-chloro-4-cyano-phenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-5-carboxamide
N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-[(1RS)-1-hydroxyethyl]-1H-pyrazole-3-carboxamide
Conditions | Yield |
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With hydrogenchloride; sodium borohydrid In ethanol; water | |
With sodium tetrahydroborate; ethanol at 22℃; for 4h; Large scale; | 214 kg |
4-bromo-2-chlorobenzonitrile
N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-[(1RS)-1-hydroxyethyl]-1H-pyrazole-3-carboxamide
Conditions | Yield |
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Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile; water / 0.5 h / Inert atmosphere; Reflux 1.2: 2.5 h / 60 - 70 °C / Inert atmosphere 2.1: hydrogenchloride / water / 2 h / 10 °C 2.2: 4 h / 0 - 5 °C 3.1: triphenylphosphine; hydrogenchloride; di-isopropyl azodicarboxylate / ethyl acetate / 10 - 20 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 10 - 20 °C / Inert atmosphere 5.1: sodium tetrahydroborate; ethanol / ethanol View Scheme | |
Multi-step reaction with 5 steps 1.1: trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate / water; tetrahydrofuran / 40 °C 2.1: hydrogenchloride / ethanol / Reflux 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere 3.2: 24 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere 5.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / tetrahydrofuran; water / 3 h / 40 °C / Inert atmosphere 2.1: hydrogenchloride / ethanol / 2 h / 30 °C / Inert atmosphere 3.1: triphenylphosphine / ethyl acetate / 0.5 h / Inert atmosphere 3.2: 3 h / 20 °C / Inert atmosphere 3.3: 1 h / 20 °C / Inert atmosphere 4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -10 °C / Inert atmosphere View Scheme |
2-Chloro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile
N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-[(1RS)-1-hydroxyethyl]-1H-pyrazole-3-carboxamide
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: hydrogenchloride / water / 2 h / 10 °C 1.2: 4 h / 0 - 5 °C 2.1: triphenylphosphine; hydrogenchloride; di-isopropyl azodicarboxylate / ethyl acetate / 10 - 20 °C / Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 10 - 20 °C / Inert atmosphere 4.1: sodium tetrahydroborate; ethanol / ethanol View Scheme | |
Multi-step reaction with 4 steps 1.1: hydrogenchloride / ethanol / Reflux 2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere 2.2: 24 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere 4.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: hydrogenchloride / water; methanol / 2 h / 10 °C 2.1: triphenylphosphine / ethyl acetate / Inert atmosphere 2.2: 10 - 20 °C / Inert atmosphere 2.3: 30 - 45 °C / Inert atmosphere 3.1: potassium tert-butylate / toluene / 1 h / 0 °C / Inert atmosphere 3.2: 2 h / 0 - 20 °C / Inert atmosphere 4.1: sodium tetrahydroborate; ethanol View Scheme | |
Multi-step reaction with 3 steps 1.1: hydrogenchloride / ethanol / 2 h / 30 °C / Inert atmosphere 2.1: triphenylphosphine / ethyl acetate / 0.5 h / Inert atmosphere 2.2: 3 h / 20 °C / Inert atmosphere 2.3: 1 h / 20 °C / Inert atmosphere 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -10 °C / Inert atmosphere View Scheme |
2-chloro-4- (1H-pyrazol-3-yl)benzonitrile
N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-[(1RS)-1-hydroxyethyl]-1H-pyrazole-3-carboxamide
Conditions | Yield |
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Multi-step reaction with 3 steps 1: triphenylphosphine; hydrogenchloride; di-isopropyl azodicarboxylate / ethyl acetate / 10 - 20 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 10 - 20 °C / Inert atmosphere 3: sodium tetrahydroborate; ethanol / ethanol View Scheme | |
Multi-step reaction with 3 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere 1.2: 24 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triphenylphosphine / ethyl acetate / Inert atmosphere 1.2: 10 - 20 °C / Inert atmosphere 1.3: 30 - 45 °C / Inert atmosphere 2.1: potassium tert-butylate / toluene / 1 h / 0 °C / Inert atmosphere 2.2: 2 h / 0 - 20 °C / Inert atmosphere 3.1: sodium tetrahydroborate; ethanol View Scheme |
N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-5-[(1RS)-1-hydroxyethyl]-1H-pyrazole-3-carboxamide
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 5 h / -10 - 30 °C 2.1: octane / 1 h / Reflux 2.2: 4 h / Reflux 3.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5 h / 25 - 30 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C View Scheme |