6-chloro-2-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-4-carbonitrile → (6-Chloro-2-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)methanamine

HRID 475129Notes

Reaction equation

HRID 475129 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:18]#[N:19])[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:17]=1>[Ni].N.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][NH2:19])[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:17]=1

Participants

4

Reactant 1

HCID 712726626-chloro-2-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-4-carbonitrile

Product 1

HCID 71272668(6-Chloro-2-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)methanamineYield 67.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A mixture of 6-chloro-2-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-4-carbonitrile (1.0 g, 3.16 mmol) and Raney nickel (100 mg) in NH3/MeOH (7 N, 10 mL) was stirred under hydrogen for 2 h. The reaction mixture was filtered with Celite® and the filtrate concentrated in vacuo to afford crude (6-chloro-2-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)methanamine (111, 600 mg, 59.0%) as a yellow solid. MS (ESI): m/z=280.3 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-f672aad8b6cb48658caf1e62b8e9c45b
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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