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Methanesulfonyl chloride → {2-[3-(4-methanesulfonyl-piperazin-1-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone

HRID 1677484
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HRID 1677484 반응식
[CH3:1][C:2]1([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:20]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1>[CH3:31][S:32]([N:28]1[CH2:29][CH2:30][N:25]([C:21]2[CH:20]=[C:19]([C:16]3[N:17]=[C:18]4[C:10]([C:8]([C:2]5([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]5)=[O:9])=[CH:11][NH:12][C:13]4=[N:14][CH:15]=3)[CH:24]=[CH:23][CH:22]=2)[CH2:26][CH2:27]1)(=[O:34])=[O:33]
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4

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HCID 31297Methanesulfonyl chlorideHCID 59540704(1-methyl-cyclohexyl)-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

생성물 1

HCID 59540692{2-[3-(4-methanesulfonyl-piperazin-1-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone수율 22.7%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
0 °C

실험 절차

A solution of (1-methyl-cyclohexyl)-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (135 mg, 0.33 mmol) in pyridine (3 ml), at 0° C., was treated with methane sulfonyl chloride (0.03 ml, 0.367 mmol). The reaction mixture was allowed to stir at 0° C. for 1.5 hours, and then room temperature for 16 hours. The reaction mixture was poured onto ice cold 1N HCl and extracted with DCM. The organic layers were collected, dried over MgSO4, filtered and concentrated giving a yellow film. The crude product was purified by preparative thin layer chromatography using 3% [5% NH4OH:MeOH]/DCM as eluant providing 36 mg (22%) of {2-[3-(4-methanesulfonyl-piperazin-1-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-(1-methyl-cyclohexyl)-methanone as an off white solid. MP 230-231° C., M+H=482.

후처리

  1. waitroom temperature for 16 hours
  2. additionThe reaction mixture was poured onto ice cold 1N HCl
  3. extractionextracted with DCM
  4. customThe organic layers were collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customgiving a yellow film
  9. customThe crude product was purified by preparative thin layer chromatography

출처 및 근거

ORD 기록
ord-4a6e6e95bcd64ff7b094d9cf4c0e4368
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08008298B2

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