Cyclohexanecarbonyl chloride → HCID 58009940, 화합물

HRID 1628105노트

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HRID 1628105 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 58009940HCID 58009940, 화합물수율 39.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-24495ad729bd4b60b4634b8d5ce58c78
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785639B2

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