Sodium borohydride → HCID 178476562, compound

HRID 897618Notes

Reaction equation

HRID 897618 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[NH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([C@H:35]3[CH2:40][CH2:39][C@@H:38]([N:41]4[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]4)[CH2:37][CH2:36]3)[N:17]=[C:18]([C:19]3[CH:34]=[CH:33][C:22]([NH:23][CH2:24][C:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:26])=[CH:21][CH:20]=3)[C:11]=12.[BH4-].[Na+]>CO>[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[NH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([C@H:35]3[CH2:36][CH2:37][C@@H:38]([N:41]4[CH2:42][CH2:43][N:44]([CH3:47])[CH2:45][CH2:46]4)[CH2:39][CH2:40]3)[N:17]=[C:18]([C:19]3[CH:20]=[CH:21][C:22]([NH:23][CH2:24][CH:25]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[OH:26])=[CH:33][CH:34]=3)[C:11]=12

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178476561HCID 178476561, compound

Product 1

HCID 178476562HCID 178476562, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of cis-2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}anilino)-1-phenyl-1-ethanone diacetate (0.050 g, 0.000077 mol) in anhydrous methanol (5 mL) was cooled to 0° C. and sodium borohydride (0.018 g, 0.0000477 mol) was added at once. The mixture was allowed to warm up to ambient temperature while stirring under an atmosphere of nitrogen for three hours. The reaction was quenched by dropwise addition of acetic acid, the reaction mixture was concentrated under reduced pressure and the residue purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1 M ammonium acetate over 25 min, 21 mL/min) to yield cis-2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}anilino)-1-phenyl-1-ethanol diacetate (0.035 g, 0.000054 mol) as a white solid.

Workup

  1. customThe reaction was quenched by dropwise addition of acetic acid
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1 M ammonium acetate over 25 min, 21 mL/min)

Sources & evidence

ORD record
ord-dfe6684760a8441e92ebf452ca8304c7
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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