Benzenesulfonyl chloride → 2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(phenylsulfonamido)benzamide

HRID 1943943노트

반응식

HRID 1943943 반응식
[NH2:1][C:2]1[C:3]([F:23])=[C:4]([C:19]([F:22])=[CH:20][CH:21]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]2[C:16]([O:17][CH3:18])=[N:15][NH:14][C:11]2=[N:12][CH:13]=1)=[O:6].[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:23][C:3]1[C:2]([NH:1][S:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])=[CH:21][CH:20]=[C:19]([F:22])[C:4]=1[C:5]([NH:7][C:8]1[CH:9]=[C:10]2[C:16]([O:17][CH3:18])=[N:15][NH:14][C:11]2=[N:12][CH:13]=1)=[O:6]

참가 물질

5

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 670889003-amino-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide

생성물 1

HCID 533133432,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(phenylsulfonamido)benzamide수율 79%

시약·촉매·용매 2

HCID 1049Pyridine촉매HCID 6212Chloroform용매

실험 절차

3-Amino-2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide (0.005 g, 0.0157 mmol) was taken up as a slurry in CHCl3 (1.0 mL). Three drops of pyridine were added, followed by the addition of benzenesulfonyl chloride (0.00600 mL, 0.0470 mmol). The slurry was stirred overnight at room temperature. The reaction mixture was concentrated and purified by silica gel chromatography to provide 2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(phenylsulfonamido)benzamide (5.7 mg, 79%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 12.59 (s, 1H), 11.01 (s, 1H), 10.39 (br s, 1H), 8.55 (s, 1H), 8.44 (s, 1H), 7.76-7.78 (m, 2H), 7.64-7.68 (m, 1H), 7.57-7.61 (m, 1H), 7.31-7.37 (m, 1H), 7.17-7.21 (m, 1H), 4.01 (s, 3H); m/z (APCI-neg) M−1=458.2.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-764732c41e3a491cb7b5f7042f196b96
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394795B2

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