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

HRID 636497ノート

反応式

HRID 636497 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a544d44396914d8aadbbfa52d4baade5
出典データセット
uspto-grants-2001_02
特許番号
US06194396B1

反応ノート

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