1,2-Dichloroethane → 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid dimethylamide

HRID 896304Notes

Reaction equation

HRID 896304 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]([C:28]([OH:30])=O)=[CH:27][C:16]=3[N:15]=2)[C:5]1=[O:31])([CH3:3])[CH3:2].C(Cl)CCl.[CH3:36][NH:37][CH3:38]>CN(C1C=CN=CC=1)C>[CH3:36][N:37]([CH3:38])[C: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]([CH3:3])[CH3:2])[C:5]3=[O:31])=[N:15][C:16]=2[CH:27]=1)=[O:30]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 223493412-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5 carboxylic acid

Product 1

HCID 208140222-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid dimethylamideYield 49%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5 carboxylic acid (42 mg, 0.1 mmol), EDC (23 mg, 0.12 mmol), DMAP (14 mg, 0.12 mmol) and dimethylamine (1M in THF, 0.12 mL) was stirred for 12 h at ambient temperature. The solvent was evaporated and the residue purified by prep-HPLC (gradient 10%-100% B) to give 22 mg (49%) of 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid dimethylamide as a white solid.

Workup

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

Sources & evidence

ORD record
ord-8ebbaac20593405bb8ae782e1a9206ec
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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