Cyclohexanecarbonyl chloride → HCID 58009940、化合物

HRID 1628105ノート

反応式

HRID 1628105 の反応式
Cl.[S:2]([N:12]1[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH2:22])[N:20]=[C:15]2[CH:14]=[CH:13]1)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH:23]1([C:29](Cl)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[S:2]([N:12]1[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH:22][C:29]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:30])[N:20]=[C:15]2[CH:14]=[CH:13]1)([C:5]1[CH:6]=[CH:7][C:8]([CH3:9])=[CH:10][CH:11]=1)(=[O:3])=[O:4]

参加物

4

反応物 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 67068339(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine hydrochloride

生成物 1

HCID 58009940HCID 58009940、化合物収率 39.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of crude (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine hydrochloride (assumed 0.498 mmol) in DCM (10 mL) was added TEA (0.208 mL, 1.49 mmol) followed by cyclohexanecarbonyl chloride (0.101 mL, 0.747 mmol). The mixture was stirred for 30 min at rt and then was diluted with DCM and washed with saturated aqueous NaHCO3 (25 mL) and brine (25 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by silica gel chromatography eluting with a gradient of 40 to 80% EtOAc in DCM to provide N-((5-Tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)cyclohexanecarboxamide as a tan solid (0.081 g, 39%). LC/MS (Table 2, Method a) Rt=2.40 min; MS m/z: 413 (M+H)+.

後処理

  1. washwashed with saturated aqueous NaHCO3 (25 mL) and brine (25 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe material was purified by silica gel chromatography
  6. washeluting with a gradient of 40 to 80% EtOAc in DCM

出典と根拠

ORDレコード
ord-24495ad729bd4b60b4634b8d5ce58c78
出典データセット
uspto-grants-2014_07
特許番号
US08785639B2

反応ノート

読み込み中…