Sodium borohydride → 8-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-[4-(1-hydroxyethyl)phenyl]-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

HRID 968133Notes

Reaction equation

HRID 968133 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:17]4[CH:19]=[C:20]([NH:23][C:24]([C:26]5[C:27]([Cl:32])=[N:28][CH:29]=[CH:30][CH:31]=5)=[O:25])[CH:21]=[CH:22][C:16]=4[CH2:15][CH2:14][C:13]=3[C:12]([C:33]([NH2:35])=[O:34])=[N:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.O>[Cl:32][C:27]1[C:26]([C:24]([NH:23][C:20]2[CH:21]=[CH:22][C:16]3[CH2:15][CH2:14][C:13]4[C:12]([C:33]([NH2:35])=[O:34])=[N:11][N:10]([C:7]5[CH:8]=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][CH:6]=5)[C:18]=4[C:17]=3[CH:19]=2)=[O:25])=[CH:31][CH:30]=[CH:29][N:28]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 222915781-(4-acetylphenyl)-8-{[(2-chloropyridin-3-yl)carbonyl]amino}-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

Product 1

HCID 222915568-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-[4-(1-hydroxyethyl)phenyl]-4,5-dihydro-1H-benzo[g]indazole-3-carboxamideYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-(4-acetylphenyl)-8-{[(2-chloropyridin-3-yl)carbonyl]amino}-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (200 mg, 0.41 mmol) in MeOH (3 mL) and water (0.3 mL) was added NaBH4 (10 mg, 0.25 mmol) at RT and stirred for 14 h. The mixture was separated on silica gel column (EtOAc) to give product (100 mg, 50%). 1H NMR was consistent with its structure.

Workup

  1. customThe mixture was separated on silica gel column (EtOAc)

Sources & evidence

ORD record
ord-0b70395d2dd84a46bf6772f1ec9f2e34
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

Loading…