Acetyl chloride → N-[2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-acetamide

HRID 896301Notes

Reaction equation

HRID 896301 reaction equation
[NH2:1][CH2:2][C:3]1[CH:30]=[CH:29][C:6]2[N:7]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:8]([CH2:10][N:11]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[N:13]([CH:20]([CH3:22])[CH3:21])[C:12]3=[O:23])=[N:9][C:5]=2[CH:4]=1.[C:31](Cl)(=[O:33])[CH3:32]>C1COCC1>[CH:20]([N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:11]([CH2:10][C:8]2[N:7]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:6]3[CH:29]=[CH:30][C:3]([CH2:2][NH:1][C:31](=[O:33])[CH3:32])=[CH:4][C:5]=3[N:9]=2)[C:12]1=[O:23])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 116758201-[5-aminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 20814107N-[2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-acetamideYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[5-aminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one (20 mg, 0.05 mmol) and TEA (10 mg, 0.10 mmol) in THF (2 ml) was added acetyl chloride (5 mg, 0.06 mmol) at room temperature and the reaction mixture was stirred for 12 h. After evaporation, the residue was purified by prep-HPLC (gradient 10%-100% B) to afford 18 mg (80%) of N-[2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-acetamide as a colorless gum.

Workup

  1. customAfter evaporation
  2. customthe residue was purified by prep-HPLC (gradient 10%-100% B)

Sources & evidence

ORD record
ord-3f5523841b8448fbb753ac3ddc88f6d0
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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