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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 1671106
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HRID 1671106 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-4bcc42e3410746688fad4457548cb7a4
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07994185B2

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