Pyridine → 2,6-Difluoro-N-(8-(4-fluorobenzenesulfonyl)-5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)benzamide

HRID 1054910노트

반응식

HRID 1054910 반응식
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:3]=1[C:4]([NH:6][C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][NH:10][C:9]=2[N:8]=1)=[O:5].N1C=CC=CC=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>ClCCl>[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:3]=1[C:4]([NH:6][C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][N:10]([S:35]([C:32]3[CH:33]=[CH:34][C:29]([F:28])=[CH:30][CH:31]=3)(=[O:37])=[O:36])[C:9]=2[N:8]=1)=[O:5]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 900116482,6-difluoro-N-(5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)benzamide

생성물 1

HCID 725439832,6-Difluoro-N-(8-(4-fluorobenzenesulfonyl)-5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2,6-Difluoro-N-(5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)benzamide (30 mg, 0.10 mmol) was dissolved in dichloromethane (0.3 mL) and pyridine (0.025 mL, 0.31 mmol). 4-Fluorobenzenesulfonyl chloride (23 mg, 0.12 mmol) was then added and the reaction mixture was stirred at room temperature for 12 hours. Next, the reaction mixture was washed with 1M HCl(aq), sat'd NaHCO3(aq), and brine. The resulting organic solution was concentrated, dissolved in DMSO, and purified by HPLC to give 2,6-difluoro-N-(8-(4-fluorobenzenesulfonyl)-5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl]benzamide. 1H NMR 250 MHz CDCl3 δ 8.13 (bs, 1H), 8.03 (dd, J=7.9, 4.3 Hz, 2H), 7.83 (d, J=7.9 Hz, 1H), 7.48 (p, J=6.5 Hz, 1H), 7.38 (d, J=7.9 Hz, 1H), 7.15 (t, J=7.9 Hz, 2H), 7.06 (t, J=7.8 Hz, 2H), 4.07 (dd, J=5.8, 4.3 Hz, 2H), 2.76 (t, J=6.5 Hz, 2H), 2.06 (p, J=5.8 Hz, 2H). LCMS (ESI): calc. C21H16F3N3O3S=447; obs. M+H=448.

후처리

  1. washNext, the reaction mixture was washed with 1M HCl(aq), sat'd NaHCO3(aq), and brine
  2. concentrationThe resulting organic solution was concentrated
  3. dissolutiondissolved in DMSO
  4. custompurified by HPLC

출처 및 근거

ORD 기록
ord-3a8b589f3bc4413eb31bee6f4b574dfe
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394315B2

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