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

HRID 457337Notes

Reaction equation

HRID 457337 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-4a759a04987b42d58a07beedaf8eb746
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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