Sodium borohydride → HCID 89691200, compound

HRID 2202941Notes

Reaction equation

HRID 2202941 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[N:21]=[C:20]([CH:22]5[CH2:25][C:24](=[O:26])[CH2:23]5)[N:19]([CH3:27])[C:18]=4[CH:28]=3)[C:10](=[O:29])[CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.CO>[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[CH:16][C:17]4[N:21]=[C:20]([CH:22]5[CH2:25][CH:24]([OH:26])[CH2:23]5)[N:19]([CH3:27])[C:18]=4[CH:28]=3)[C:10](=[O:29])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 89690334HCID 89690334, compound

Product 1

HCID 89691200HCID 89691200, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-((4-fluorobenzyl)oxy)-1-(1-methyl-2-(3-oxocyclobutyl)-1H-benzimidazol-6-yl)pyridin-2(1H)-one (80 mg) in a mixture of THF (10 ml) and MeOH (3 ml) was added NaBH4 (15 mg) at 0° C. The mixture was then allowed to warm to room temperature, and stirred for 3 h. The reaction mixture was then quenched with saturated NH4Cl (5 ml), and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (50 mg) as an off-white solid.

Workup

  1. customThe reaction mixture was then quenched with saturated NH4Cl (5 ml)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-a39cd74e23304fd5a4723be518079ae3
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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