Reaktion #649231

ord-f3b65e95296a4fca9cda4f1322784837

Reaktionsgleichung

CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(C=O)c4)cc23)CC1
3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide
CC(C)[C@@H](N)CO
(2R)-2-amino-3-methyl-1-butanol
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
→
CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(CN[C@@H](CO)C(C)C)c4)cc23)CC1
title compound
Ausbeute 32.5%
CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(CN[C@@H](CO)C(C)C)c4)cc23)CC1
3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[3-({[(1R)-1-(hydroxymethyl)-2-methylpropyl]amino}methyl)phenyl]-1H-indole-7-carboxamide
Ausbeute 32.5%

Edukte

CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4cccc(C=O)c4)cc23)CC1
3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide
CC(C)[C@@H](N)CO
(2R)-2-amino-3-methyl-1-butanol
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewere reacted

Vorschrift

Following the general procedure of example 16, 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (50 mg, 0.114 mmol), (2R)-2-amino-3-methyl-1-butanol (10.2 mg, 0.087 mmol) and NaBH(OAc)3 (58 mg, 0.261 mmol) were reacted to give the title compound (14.9 mg, 25%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08063071B2uspto-grants-2011_11