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Dioxirane → (RS) N-cyclopropyl-4-{6-[4-(cyclopropylsulfinyl)phenyl]-8-(isobutylamino)imidazo[1,2-a]pyrazin-3-yl}benzamide

HRID 925598
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HRID 925598 반응식
[CH:1]1([NH:4][C:5](=[O:36])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[CH:17]=[C:18]([C:26]5[CH:31]=[CH:30][C:29]([S:32][CH:33]6[CH2:35][CH2:34]6)=[CH:28][CH:27]=5)[N:19]=[C:20]([NH:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:15]4=[N:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[O:37]1CO1>ClCCl.CC(C)=O>[CH:1]1([NH:4][C:5](=[O:36])[C:6]2[CH:7]=[CH:8][C:9]([C:12]3[N:16]4[CH:17]=[C:18]([C:26]5[CH:27]=[CH:28][C:29]([S:32]([CH:33]6[CH2:35][CH2:34]6)=[O:37])=[CH:30][CH:31]=5)[N:19]=[C:20]([NH:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:15]4=[N:14][CH:13]=3)=[CH:10][CH:11]=2)[CH2:3][CH2:2]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 449520DioxiraneHCID 67973399N-cyclopropyl-4-{6-[4-(cyclopropylsulfanyl)phenyl]-8-(isobutylamino)imidazo[1,2-a]pyrazin-3-yl}benzamide

생성물 1

HCID 67973689(RS) N-cyclopropyl-4-{6-[4-(cyclopropylsulfinyl)phenyl]-8-(isobutylamino)imidazo[1,2-a]pyrazin-3-yl}benzamide수율 59%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6344
Dichloromethane
용매

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온도
23 °C

실험 절차

A solution of 50 mg (100 μmol) N-cyclopropyl-4-{6-[4-(cyclopropylsulfanyl)phenyl]-8-(isobutylamino)imidazo[1,2-a]pyrazin-3-yl}benzamide in 5.0 mL dichloromethane was cooled to −30° C. and 1.16 mL of a 0.15 molar dioxirane solution in acetone were added. After 15 minutes of stirring the mixture was warmed to 23° C., the solvent removed and the residue was purified by chromatography to give 33.3 mg (59%) of the title compound. 1H-NMR (CDCl3): δ=0.67 (2H), 0.86-1.05 (5H), 1.06 (3H), 1.07 (3H), 1.25 (1H), 2.09 (1H), 2.28 (1H), 2.95 (1H), 3.56 (2H), 6.36 (1H), 6.54 (1H), 7.60 (1H), 7.63 (2H), 7.70 (2H), 7.94 (2H), 7.96 (1H), 8.02 (2H) ppm.

후처리

  1. customthe solvent removed
  2. customthe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-83440da6d6944a87a99d551ac22b8bd9
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284317B2

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