HCID 71272259, compound → HCID 71272197, compound

HRID 475156Notes

Reaction equation

HRID 475156 reaction equation
[F:1][C:2]1[C:16]([C:17]#[N:18])=[CH:15][C:5]2[N:6]([CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][O:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1>[Ni].N.CO>[F:1][C:2]1[C:16]([CH2:17][NH2:18])=[CH:15][C:5]2[N:6]([CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][O:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 71272259HCID 71272259, compound

Product 1

HCID 71272197HCID 71272197, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A mixture of 5-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-6-carbonitrile (1.2 g, 4.9 mmol) and Raney nickel (40 mg) in NH3/MeOH solution (7 N, 20 mL) was stirred under hydrogen at RT overnight. The reaction mixture was filtered through Celite® and the filtrate concentrated in vacuo to afford (5-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-6-yl)methanamine as an oil (350 mg, 28.7%). MS (ESI): m/z=250 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-fde72a0f83b3420d9d32e2cba693f68c
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

Loading…