Methylamine → 1-Isobutyl-2-amino-6-(1-methyl-4-phenyl-1H-imidazol-5-yl)-1H-benzimidazole

HRID 250773Notes

Reaction equation

HRID 250773 reaction equation
[CH2:1]([N:5]1[C:9]2[CH:10]=[C:11]([CH:14]=[N:15][CH3:16])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[NH2:17])[CH:2]([CH3:4])[CH3:3].C1(C)C=CC(S([CH:27]([N+:34]#[C-:35])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=O)=O)=CC=1.CN>CO>[CH2:1]([N:5]1[C:9]2[CH:10]=[C:11]([C:14]3[N:15]([CH3:16])[CH:35]=[N:34][C:27]=3[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[NH2:17])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 10967613a-Tosylbenzyl isocyanideHCID 668688601-Isobutyl-2-amino-6-(methyliminomethyl)-1H-benzimidazole

Product 1

HCID 668692921-Isobutyl-2-amino-6-(1-methyl-4-phenyl-1H-imidazol-5-yl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Heat a mixture of 1-isobutyl-2-amino-6-(methyliminomethyl)-1H-benzimidazole (504 mg, 2.19 mmol), α-(p-toluenesulfonyl)benzylisocyanide (1.48 g, 5.47 mmol), methanol (7 mL), and methylamine (5.5 mL, 2M in tetrahydrofuran) in a sealed tube at 80° C. for 20 hours. Cool to room temperature and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with a 1:1 mixture of acetonitrile and dichloromethane containing 5% methanol to provide the desired compound.

Workup

  1. temperatureHeat
  2. concentrationconcentrate under reduced pressure
  3. washSubject residue to silica gel chromatography, eluting with a 1:1 mixture of acetonitrile and dichloromethane containing 5% methanol

Sources & evidence

ORD record
ord-af8a6c8430e44ec6bc3b533b0d143b86
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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