Dimethylamine, hydrochloride → 4-[2,6-dichloro-3-[N-methyl-N-[4-(methyl-carbamoyl)cinnamoylglycyl]amino]-benzyloxy]-2-ethyl-1-dimethylcarbamoylmethyl-1H-benzimidazole

HRID 636497Notes

Reaction equation

HRID 636497 reaction equation
[C:1]([CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH2:15][C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([N:23]([CH3:42])[C:24](=[O:41])[CH2:25][NH:26][C:27](=[O:40])[CH:28]=[CH:29][C:30]4[CH:35]=[CH:34][C:33]([C:36](=[O:39])[NH:37][CH3:38])=[CH:32][CH:31]=4)[C:17]=3Cl)[C:8]=2[N:7]=[C:6]1[CH2:44][CH3:45])(O)=[O:2].[ClH:46].[CH3:47][NH:48][CH3:49].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[Cl:46][C:17]1[C:18]([N:23]([CH3:42])[C:24](=[O:41])[CH2:25][NH:26][C:27](=[O:40])[CH:28]=[CH:29][C:30]2[CH:35]=[CH:34][C:33]([C:36](=[O:39])[NH:37][CH3:38])=[CH:32][CH:31]=2)=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[CH2:15][O:14][C:13]1[C:8]2[N:7]=[C:6]([CH2:44][CH3:45])[N:5]([CH2:4][C:1](=[O:2])[N:48]([CH3:49])[CH3:47])[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 542002691-carboxymethyl-4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-2-ethyl-1H-benzimidazole

Product 1

HCID 539554454-[2,6-dichloro-3-[N-methyl-N-[4-(methyl-carbamoyl)cinnamoylglycyl]amino]-benzyloxy]-2-ethyl-1-dimethylcarbamoylmethyl-1H-benzimidazoleYield 73.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-carboxymethyl-4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]-benzyloxy]-2-ethyl-1H-benzimidazole (60 mg), dimethylamine hydrochloride (11.2 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (17.1 mg) and 1-hydroxybenzotriazole (18.6 mg) in dimethylformamide (1 ml) was stirred for 1 day at ambient temperature. To the reaction mixture was added water, and the mixture was extracted with chloroform. The organic layer was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (10% methanol—chloroform) to give 4-[2,6-dichloro-3-[N-methyl-N-[4-(methyl-carbamoyl)cinnamoylglycyl]amino]-benzyloxy]-2-ethyl-1-dimethylcarbamoylmethyl-1H-benzimidazole (46 mg) as amorphous.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (10% methanol—chloroform)

Sources & evidence

ORD record
ord-a544d44396914d8aadbbfa52d4baade5
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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