Dichloromethane → HCID 178510989、化合物

HRID 732848ノート

反応式

HRID 732848 の反応式
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)/[C:6](=[C:13](/OCC)\[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)/[C:5]1=[O:23])(=[O:3])C.C(OC(=O)[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=1)(C)(C)C.ClCCl>CN(C=O)C.CO>[OH-:3].[NH4+:4].[NH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:46])[C:39]1[CH:44]=[CH:43][C:42]([NH:45]/[C:13](=[C:6]2\[C:5](=[O:23])[NH:4][C:12]3[C:7]\2=[CH:8][CH:9]=[CH:10][CH:11]=3)/[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:41][CH:40]=1

参加物

7

反応物 3

HCID 6344DichloromethaneHCID 11045014HCID 11045014、化合物HCID 58720810Carbamic acid, [6-[(4-aminobenzoyl)amino]hexyl]-, 1,1-dimethylethyl ester

生成物 2

HCID 14923Ammonium Hydroxide収率 10%HCID 178510989HCID 178510989、化合物収率 162%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

1-Acetyl-3-[1-ethoxy-1-phenyl-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one (50 mg, 0.163 mmol) and [6-(4-amino-benzoylamino)-hexyl]-carbamic acid tert-butyl ester (65 mg, 0.195 mmol) were combined in DMF (1 mL) and stirred for 24 hours at 110° C. The DMF was removed by rotary evaporation under high vacuum. The residue was re-dissovled in MeOH (1 mL), a solution of 0.5 M sodium methoxide was added (0.5 mL) and the reaction was stirred at ambient temperature for 1 hour. 4N HCl in dioxane(1 mL) was added and the reaction was stirred overnight. The reaction was concentrated by rotary evaporation. Flash chromatography in a polar gradient of [20%(10% ammonium hydroxide in MeOH) and 80% dichloromethane] provided 60 mg of N-(6-amino-hexyl)-4-({[2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-phenyl-methyl}-amino)-benzamide (82% yield).

後処理

  1. customThe DMF was removed by rotary evaporation under high vacuum
  2. additiona solution of 0.5 M sodium methoxide was added (0.5 mL)
  3. stirringthe reaction was stirred at ambient temperature for 1 hour
  4. addition4N HCl in dioxane(1 mL) was added
  5. stirringthe reaction was stirred overnight
  6. concentrationThe reaction was concentrated by rotary evaporation

出典と根拠

ORDレコード
ord-ba8e41a433e84f37b537274615461d9b
出典データセット
uspto-grants-2009_09
特許番号
US07588899B2

反応ノート

読み込み中…