Sodium borohydride → HCID 178504854, compound

HRID 1500943Notes

Reaction equation

HRID 1500943 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]2[N:6]([C@H:23]3[CH2:26][C@H:25]([C:27](OCC)=[O:28])[CH2:24]3)[C:7]([CH2:9][N:10]3[C:14]4=[CH:15][N:16]=[CH:17][CH:18]=[C:13]4[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:11]3)=[N:8][C:4]=2[CH:3]=1.[BH4-].[Na+]>CCO>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]2[N:6]([C@H:23]3[CH2:24][C@H:25]([CH2:27][OH:28])[CH2:26]3)[C:7]([CH2:9][N:10]3[C:14]4=[CH:15][N:16]=[CH:17][CH:18]=[C:13]4[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:11]3)=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178472512HCID 178472512, compound

Product 1

HCID 178504854HCID 178504854, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl trans-3-(5-chloro-2-{[3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridin-1-yl]methyl}-1H-benzimidazol-1-yl)cyclobutanecarboxylate (80 mg, 0.16 mmol) in EtOH was added NaBH4 (80 mg, 2.1 mmol) in portions at RT. The mixture was then heated at 60° C. for 1 hour. The reaction was completed as indicated by LC/MS. The mixture was quenched with 1N HCl to pH7. After the solvent was removed by concentration, the residue was purified by preparative-HPLC to afford 15.1 mg of [trans-3-(5-chloro-2-{[3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridin-1-yl]methyl}-1H-benzimidazol-1-yl)cyclobutyl]methanol as a white solid.

Workup

  1. customThe mixture was quenched with 1N HCl to pH7
  2. customAfter the solvent was removed by concentration
  3. customthe residue was purified by preparative-HPLC

Sources & evidence

ORD record
ord-a410aded39d94beba158f26ce61f1814
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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