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

HRID 2287573노트

반응식

HRID 2287573 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e7215c1ac7724811bb1215ebd9da15e3
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06083961

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