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Triethylamine → 3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

HRID 2267491
ノート
印刷プレビュー

反応式

HRID 2267491 の反応式
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=2)[NH:12][CH:11]=[C:10]3[CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:32][CH2:33][CH2:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[Cl:32][CH2:33][CH2:34][S:35]([N:22]1[CH2:23][CH2:24][CH:19]([C:10]2[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:8]=3)[NH:12][CH:11]=2)[CH2:20][CH2:21]1)(=[O:37])=[O:36]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 114271625-Phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide

生成物 1

HCID 590033063-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide収率 32%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5-phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide (65 mg, 0.2 mmol) in CH2Cl2 (5 mL) at 0° C., triethylamine (0.11 mL, 0.8 mmol) and 2-chloroethanesulfonyl chloride (0.042 mL, 0.4 mmol) were added. After stirring at 0° C. for 30 min. the reaction mixture was partitioned between CH2Cl2 and water. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×). The combined organic phase was dried over magnesium sulfate and the solvent removed under reduced pressure. The resulting residue was purified by filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL) to give the desired product (26 mg, 32%).

後処理

  1. customwas partitioned between CH2Cl2 and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  4. dry with materialThe combined organic phase was dried over magnesium sulfate
  5. customthe solvent removed under reduced pressure
  6. filtrationThe resulting residue was purified by filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL)

出典と根拠

ORDレコード
ord-ea224ef05d6e49f5a75e75a0684f76a7
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07858796B2

反応ノート

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