4-Methoxybenzylamine → (E)-4-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]-N-(4-methoxybenzyl)benzamide hydrochloride

HRID 48355ノート

反応式

HRID 48355 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1Cl)[CH:5]=[CH:6][C:7]1=[N:8][CH2:9][CH2:10][N:11]([CH2:18]C(O)=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2.Cl.[CH3:27]N(C)CCCN=C=NCC.[OH2:38].ON1C2C=CC=CC=2N=N1.[CH3:49][O:50][C:51]1[CH:58]=[CH:57][C:54]([CH2:55][NH2:56])=[CH:53][CH:52]=1>ClCCl>[ClH:1].[CH3:18][N:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:7](/[CH:6]=[CH:5]/[C:4]2[CH:22]=[CH:23][C:24]([C:27]([NH:56][CH2:55][C:54]3[CH:57]=[CH:58][C:51]([O:50][CH3:49])=[CH:52][CH:53]=3)=[O:38])=[CH:2][CH:3]=2)=[N:8][CH2:9][CH2:10]1

参加物

6

反応物 4

HCID 754524-MethoxybenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69892105(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine-1-acetic acid

生成物 1

HCID 22742210(E)-4-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]-N-(4-methoxybenzyl)benzamide hydrochloride収率 13.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 50 mg (0.164 mmol) of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine-1-acetic acid, 38 mg (0.199 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, 27 mg (0.199 mmol) of 1-hydroxybenzotriazole hydrate and 0.021 ml (0.145 mmol) of 4-methoxybenzylamine was stirred in 5 ml of dichloromethane for 3 hours at room temperature and then left to stand at 4° C. for 54 hours. The solution was diluted with dichloromethane and then sequentially washed with citric acid, saturated sodium bicarbonate solution and brine, dried over magnesium sulphate, filtered and evaporated to dryness. The residue was chromatographed twice on silica gel using sequentially dichloromethane/methanol (98:2), dichloromethane/methanol (97:3) and dichloromethane/methanol (95:5) for the elutions. The product was dissolved in a solution of hydrogen chloride in ether and evaporated to dryness. There was obtained 9 mg of (E)-4-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]-N-(4-methoxybenzyl)benzamide hydrochloride as a red oil MS: m/e 426.3 [M+H]+.

後処理

  1. waitleft
  2. washsequentially washed with citric acid, saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was chromatographed twice on silica gel using sequentially dichloromethane/methanol (98:2), dichloromethane/methanol (97:3) and dichloromethane/methanol (95:5) for the elutions
  7. dissolutionThe product was dissolved in a solution of hydrogen chloride in ether
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-326e7edb28ba4d02848a1a7c32790d66
出典データセット
uspto-grants-2004_03
特許番号
US06703387B2

反応ノート

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