Sodium borohydride → HCID 89763461, compound

HRID 707356Notes

Reaction equation

HRID 707356 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:15][CH:14]([N:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[N:18]=[C:17]2[O:25][CH3:26])[CH2:13]1)=[O:11].[BH4-].[Na+]>O1CCCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([CH:12]1[CH2:15][CH:14]([N:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[N:18]=[C:17]2[O:25][CH3:26])[CH2:13]1)[OH:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 89763770HCID 89763770, compound

Product 1

HCID 89763461HCID 89763461, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1H-benzo[d]imidazol-2-yl)(3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)methanone (60 mg, 0.17 mmol) was dissolved in dry tetrahydrofuran (10 mL) and treated with sodium borohydride (11 mg, 0.29 mmol). The reaction was stirred at room temperature until the starting material was consumed by TLC. After that, the reaction solution was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel, followed by prep. TLC (dichloromethane:methanol=10:1) to give two isomers of (1H-benzo[d]imidazol-2-yl)-3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)methanol as mixtures of diastereomers. M+1: 367.

Workup

  1. customwas consumed by TLC
  2. concentrationAfter that, the reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel
  4. customTLC (dichloromethane:methanol=10:1) to give two isomers of (1H-benzo[d]imidazol-2-yl)-3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclobutyl)methanol as mixtures of diastereomers

Sources & evidence

ORD record
ord-81951b853e1a474f93a70780c5b5f7fe
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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