Methylamine → 1-[5-methylaminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one

HRID 896307Notes

Reaction equation

HRID 896307 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][C:26]([CH2:28]OS(C)(=O)=O)=[CH:27][C:16]=3[N:15]=2)[C:5]1=[O:34])([CH3:3])[CH3:2].[CH3:35][NH2:36]>>[CH3:35][NH:36][CH2:28][C:26]1[CH:25]=[CH:24][C:17]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:14]([CH2:13][N:6]3[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[N:4]([CH:1]([CH3:2])[CH3:3])[C:5]3=[O:34])=[N:15][C:16]=2[CH:27]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 20813972methanesulfonic acid 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl ester

Product 1

HCID 208139711-[5-methylaminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-oneYield 94%

Procedure

A mixture of methanesulfonic acid 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl ester (10 mg, 0.02 mmol) and methylamine (1M in THF, 0.5 mL) was stirred at ambient temperature for 12 h then the solvent evaporated. The residue was purified by prep-HPLC (gradient 10%-100% B) to give 8.1 mg (94%) of 1-[5-methylaminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one as a colorless gum.

Workup

  1. customthe solvent evaporated
  2. customThe residue was purified by prep-HPLC (gradient 10%-100% B)

Sources & evidence

ORD record
ord-e92b4b7172324ae6b80d27cf76a67f6a
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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