2-Methoxyethylamine → HCID 69892592、化合物

HRID 48352ノート

反応式

HRID 48352 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH:5]=[CH:6][C:7]1=[N:8][CH2:9][CH2:10][N:11]([CH2:18][C:19]([OH:21])=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2.[ClH:26].CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:49][O:50][CH2:51][CH2:52][NH2:53]>ClCCl>[ClH:1].[ClH:26].[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH:5]=[CH:6][C:7]1=[N:8][CH2:9][CH2:10][N:11]([CH2:18][C:19]([NH:53][CH2:52][CH2:51][O:50][CH3:49])=[O:21])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2

参加物

6

反応物 4

HCID 80182-MethoxyethylamineHCID 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 69892592HCID 69892592、化合物収率 22.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 33 mg (0.088 mmol) of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine-1-acetic acid, 30 mg (0.157 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, 16 mg (0.105 mmol) of 1-hydroxybenzotriazole hydrate and 14 mg (0.187 mmol) of 2-methoxyethylamine was stirred in 3 ml of dichloromethane for 3 hours. The solution was washed with saturated sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated to dryness. The residue was chromatographed three times on silica gel using dichloromethane/methanol (94:6), dichloromethane/methanol 92:8) and ethyl acetate/methanol (9:1) for the elutions. The product was dissolved in a solution of hydrogen chloride in ethyl acetate, evaporated to dryness and the residue triturated with diethyl ether. There was obtained 5 mg of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-N-(2-methoxyethyl)-1H-1,4-benzodiazepin-1-acetamide dihydrochloride as a red solid. MS: m/e 431.9 [M+H]+.

後処理

  1. washThe solution was washed with saturated sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was chromatographed three times on silica gel
  6. dissolutionThe product was dissolved in a solution of hydrogen chloride in ethyl acetate
  7. customevaporated to dryness
  8. customthe residue triturated with diethyl ether

出典と根拠

ORDレコード
ord-e11089c136ae486ab43fbbec7a24bff8
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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