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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Methanesulfonyl chloride → N-(3-{5-(2-Chloro-4-pyrimidinyl)-2-[4-(methylsulfonyl)-1-piperazinyl]-1,3-thiazol-4-yl}-2-fluorophenyl)-2,5-difluorobenzenesulfonamide

HRID 1961928
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HRID 1961928 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[N:12]=[C:11]([C:13]2[S:17][C:16]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[N:15][C:14]=2[C:24]2[C:25]([F:42])=[C:26]([NH:30][S:31]([C:34]3[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=3[F:41])(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=2)[CH:10]=[CH:9][N:8]=1>C(Cl)Cl>[Cl:6][C:7]1[N:12]=[C:11]([C:13]2[S:17][C:16]([N:18]3[CH2:23][CH2:22][N:21]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:20][CH2:19]3)=[N:15][C:14]=2[C:24]2[C:25]([F:42])=[C:26]([NH:30][S:31]([C:34]3[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=3[F:41])(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=2)[CH:10]=[CH:9][N:8]=1
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참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 57989746N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-piperazinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide

생성물 1

HCID 57989647N-(3-{5-(2-Chloro-4-pyrimidinyl)-2-[4-(methylsulfonyl)-1-piperazinyl]-1,3-thiazol-4-yl}-2-fluorophenyl)-2,5-difluorobenzenesulfonamide수율 32.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Methanesulfonyl chloride (0.05 mL, 0.7 mmol) was added to a stirring solution of N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1-piperazinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide (0.40 g, 0.66 mmol) and TEA (0.32 mL, 2.3 mmol) in DCM (10 mL) at rt. LCMS analysis indicated clean conversion to product. The reaction was quenched with water and the whole was extracted with DCM. The combined organic extracts were dried over MgSO4, filtered, and the filtrate was concentrated onto silica gel. Purification by flash chromatography afforded the title compound of Step D (0.14 g, 30% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.80 (s, 1H), 8.34 (d, J=5.5 Hz, 1H), 7.25-7.63 (m, 5H), 6.50 (d, J=5.3 Hz, 1H), 3.69 (br. s., 4H), 3.27 (br. s., 4H), 2.93 (s, 3H).

후처리

  1. customThe reaction was quenched with water
  2. extractionthe whole was extracted with DCM
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated onto silica gel
  6. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-ae932b4abcf04e79b9412bb68885f9d5
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415345B2

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