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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,6-difluoro-N-(3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide

HRID 1943939
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HRID 1943939 반응식
[F:1][CH2:2][CH2:3][O:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[NH:7][N:6]=1.[F:15][C:16]1[C:24]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])=[CH:23][CH:22]=[C:21]([F:32])[C:17]=1[C:18](O)=[O:19].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[F:15][C:16]1[C:24]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28])=[CH:23][CH:22]=[C:21]([F:32])[C:17]=1[C:18]([NH:14][C:11]1[CH:12]=[C:13]2[C:5]([O:4][CH2:3][CH2:2][F:1])=[N:6][NH:7][C:8]2=[N:9][CH:10]=1)=[O:19]
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7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 442237483-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-amineHCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acid

생성물 1

HCID 866525062,6-difluoro-N-(3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-amine (0.020 g, 0.10 mmol), 2,6-difluoro-3-(propylsulfonamido)benzoic acid (0.031 g, 0.11 mmol), EDCI (0.021 g, 0.11 mmol), and HOBt (0.017 g, 0.11 mmol) in DMF (6 mL) was stirred at room temperature for 1 hour. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give 2,6-difluoro-N-(3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide. The crude material was purified by silica gel flash column chromatography (5% 7N NH3-MeOH in CH2Cl2) to afford 2,6-difluoro-N-(3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (41 mg, 88% yield). LRMS (ACPI pos) m/e 458.1 (M+1). 1H-NMR (400 MHz, d6-DMSO) δ 12.68 (s, 1H), 11.12 (s, 1H), 9.73 (br s, 1H), 8.58 (d, 1H), 8.54 (d, 1H), 7.55 (q, 1H), 7.27 (t, 1H), 4.90 (m, 1H), 4.78 (m, 1H), 4.63 (m, 1H), 4.55 (m, 1H), 3.12 (t, 2H), 1.76 (m, 2H), 0.99 (t, 3H); 19F NMR (376 MHz, DMSO) δ−117.3, −122.6, −223.1.

후처리

  1. washwashed with saturated aqueous NH4Cl, saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-107cf8fa4c9142caaee3fc136cff0389
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08394795B2

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