Acryloyl chloride → 4-(4-Acryloylamino-piperidine-1-sulfonyl)-2-fluoro-N-phenethyl-benzamide

HRID 337220ノート

反応式

HRID 337220 の反応式
C(N(C(C)C)CC)(C)C.[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:36]=[CH:35][C:23]([C:24]([NH:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:25])=[C:22]([F:37])[CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1.[C:38](Cl)(=[O:41])[CH:39]=[CH2:40]>C1COCC1.C(Cl)Cl>[C:38]([NH:10][CH:11]1[CH2:12][CH2:13][N:14]([S:17]([C:20]2[CH:36]=[CH:35][C:23]([C:24]([NH:26][CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:25])=[C:22]([F:37])[CH:21]=2)(=[O:18])=[O:19])[CH2:15][CH2:16]1)(=[O:41])[CH:39]=[CH2:40]

参加物

6

反応物 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 710600854-(4-Amino-piperidine-1-sulfonyl)-2-fluoro-N-phenethyl-benzamide

生成物 1

HCID 866740874-(4-Acryloylamino-piperidine-1-sulfonyl)-2-fluoro-N-phenethyl-benzamide収率 25%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Diisopropylethylamine (0.51 ml, 3.0 mmol) was added in one portion to a stirred solution of 4-(4-Amino-piperidine-1-sulfonyl)-2-fluoro-N-phenethyl-benzamide (0.24 g, 0.6 mmol) in THF (10 ml), followed by the drop wise addition of acryloyl chloride (0.05 ml, 0.66 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was diluted with DCM (20 ml) and washed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml). The organic layer was separated, dried (MgSO4), filtered, concentrated and the resulting residue was purified by flash column chromatography (elution: 98% DCM, 2% Methanol) to give the title compound (0.06 g, 25% yield) as a white solid.

後処理

  1. washwashed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe resulting residue was purified by flash column chromatography (elution: 98% DCM, 2% Methanol)

出典と根拠

ORDレコード
ord-0667b9706bd5435299fe90ddddf95502
出典データセット
uspto-grants-2014_11
特許番号
US08889716B2

反応ノート

読み込み中…