Cyclohexanecarbonyl chloride → HCID 58009940, 화합물

HRID 1969530노트

반응식

HRID 1969530 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.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>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

6

반응물 4

HCID 75938Cyclohexanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 67068339(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine hydrochloride

생성물 1

HCID 58009940HCID 58009940, 화합물수율 80.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a slurry of (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine hydrochloride (0.50 g, 1.476 mmol, Example #5, Step C) in DCM (10 mL) was added cyclohexanecarbonyl chloride (0.221 mL, 1.623 mmol) followed by DIEA (0.644 mL, 3.69 mmol). The reaction mixture was stirred for about 4 h at ambient temperature and then saturated aqueous NaHCO3 (20 mL) and DCM (20 mL) were added to the reaction mixture. The organic layer was separated, concd in vacuo, and purified by chromatography on silica gel (40 g) eluting with 20-80% EtOAc in DCM to provide N-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)cyclohexanecarboxamide (0.49 g, 80%) as a colorless solid: LC/MS (Table 1, Method a) Rt=2.40 min; MS m/z: 413 (M+H)+.

후처리

  1. customThe organic layer was separated
  2. customconcd in vacuo, and purified by chromatography on silica gel (40 g)
  3. washeluting with 20-80% EtOAc in DCM

출처 및 근거

ORD 기록
ord-1a25765901c54371a507f252d47e0201
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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