1,4-Dioxane hydrochloride → 3-(2-fluorophenyl)-5-(1H-imidazol-5-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1775033노트

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HRID 1775033 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[CH:12][N:13]=[C:14]([C:17]3[N:21](C4CCCCO4)[CH:20]=[N:19][CH:18]=3)[CH:15]=2)[N:10](C2CCCCO2)[N:9]=1.O1CCOCC1.Cl>CC#N>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[CH:12][N:13]=[C:14]([C:17]3[NH:21][CH:20]=[N:19][CH:18]=3)[CH:15]=2)[NH:10][N:9]=1

참가 물질

4

반응물 2

HCID 204431481,4-Dioxane hydrochlorideHCID 712541713-(2-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-imidazol-5-yl)-1H-pyrazolo[3,4-c]pyridine

생성물 1

HCID 712536833-(2-fluorophenyl)-5-(1H-imidazol-5-yl)-1H-pyrazolo[3,4-c]pyridine수율 21.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
25 °C

실험 절차

In a 50 mL round bottom flask was added 3-(2-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-imidazol-5-yl)-1H-pyrazolo[3,4-c]pyridine (150 mg, 0.33 mmol) and 4 N HCl— dioxane (5 mL). The mixture was stirred at 25° C. for 2 h. The solvent was distilled off. The crude product was purified via reverse phase HPLC eluting with 35% CH3CN in aqueous 10 mmol NH4HCO3 solution to afford 218 as a white solid (20 mg, 21%). 1H NMR (500 MHz, DMSO) δ 13.93 (s, 1H), 12.21 (s, 1H), 9.05 (s, 1H), 8.20 (s, 1H), 7.86 (t, J=7.0, 1H), 7.71 (s, 1H), 7.62 (s, 1H), 7.56-7.54 (m, 1H), 7.46 (t, J=10.0, 1H), 7.41 (t, J=7.5, 1H). ESI MS m/z=280 (M+1)

후처리

  1. distillationThe solvent was distilled off
  2. customThe crude product was purified via reverse phase HPLC

출처 및 근거

ORD 기록
ord-068a3452cbc041bd93a30b61117c256b
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260425B2

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