1-Propanesulfonyl chloride → N-{1-benzenesulfonyl-4-[1-(propane-1-sulfonyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-cyano-acetamide

HRID 1257600ノート

反応式

HRID 1257600 の反応式
C(N(C(C)C)CC)(C)C.[CH2:10]([S:13](Cl)(=[O:15])=[O:14])[CH2:11][CH3:12].[C:17]1([S:23]([N:26]2[C:30]3=[N:31][CH:32]=[C:33]([NH:42][C:43](=[O:47])[CH2:44][C:45]#[N:46])[C:34]([NH:35][CH:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[C:29]3[CH:28]=[CH:27]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:17]1([S:23]([N:26]2[C:30]3=[N:31][CH:32]=[C:33]([NH:42][C:43](=[O:47])[CH2:44][C:45]#[N:46])[C:34]([NH:35][CH:36]4[CH2:41][CH2:40][N:39]([S:13]([CH2:10][CH2:11][CH3:12])(=[O:15])=[O:14])[CH2:38][CH2:37]4)=[C:29]3[CH:28]=[CH:27]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 662791-Propanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67379316N-[1-benzenesulfonyl-4-(piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyano-acetamide

生成物 1

HCID 67342235N-{1-benzenesulfonyl-4-[1-(propane-1-sulfonyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-cyano-acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

Diisopropylethylamine (0.107 ml, 0.615 mmol) and 1-propanesulfonyl chloride (0.035 ml, 0.308 mmol) were added sequentially to a solution of N-[1-benzenesulfonyl-4-(piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-cyano-acetamide (hydrochloride salt) (0.205 mmol) in CH2Cl2 (2 ml) at 25° C. The reaction mixture was stirred for 3 h at 25° C., then was partitioned between saturated NaHCO3 (6 ml) and CH2Cl2 (2 ml). The phases were separated using a phase separation column (Biotage) and the organic layer was concentrated under reduced pressure to give crude N-{1-benzenesulfonyl-4-[1-(propane-1-sulfonyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-cyano-acetamide as a brown oil/solid. LCMS (Method G, ESI): RT=0.88 min, m+H=545.3. This material was used in the next step below without additional purification or characterization.

後処理

  1. customwas partitioned between saturated NaHCO3 (6 ml) and CH2Cl2 (2 ml)
  2. customThe phases were separated
  3. customa phase separation column (Biotage)
  4. concentrationthe organic layer was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-f8f9860aafb34080842809f1d60ab7d0
出典データセット
uspto-grants-2013_06
特許番号
US08461328B2

反応ノート

読み込み中…