Trifluoroacetic acid → Trifluoroacetic acid

HRID 1529353노트

반응식

HRID 1529353 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14](C1CCCCO1)[N:13]=[C:12]2[C:24]1[N:29]=[C:28]([O:30][C@H:31]2[CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35][C:32]32[CH2:34][CH2:33]3)[CH:27]=[N:26][CH:25]=1.[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]>C(Cl)Cl>[CH2:34]1[C:32]2([CH2:35][CH2:36][NH:37][CH2:38][C@@H:31]2[O:30][C:28]2[N:29]=[C:24]([C:12]3[C:11]4[C:15](=[CH:16][CH:17]=[C:9]([C:3]5[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=5[F:1])[CH:10]=4)[NH:14][N:13]=3)[CH:25]=[N:26][CH:27]=2)[CH2:33]1.[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 67959729HCID 67959729, 화합물

생성물 2

HCID 6422Trifluoroacetic acid수율 55.3%HCID 67960061HCID 67960061, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (4R)-tert-butyl 4-(6-(5-(2,6-difluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (0.983 g, 1.591 mmol) in 8 mL DCM was added TFA (3.68 mL, 47.7 mmol). After 6 h at RT, the orange reaction was placed in the freezer overnight, and in the morning was warmed and stirred at RT for 3 h. The reaction was concentrated in vacuo, then taken up in DMSO (6 mL total), filtered, and purified by RPHPLC, 20-70% ACN/H2O with 0.1% TFA; product-containing fractions were combined and concentrated in vacuo to give (R)-3-(6-(6-azaspiro[2.5]octan-4-yloxy)pyrazin-2-yl)-5-(2,6-difluorophenyl)-1H-indazole*1.5 TFA (0.530 g, 0.88 mmol, 55% yield) yellow solid: MS (ESI, pos. ion) m/z: 434 (M+1).

후처리

  1. customthe orange reaction
  2. customwas placed in the freezer overnight
  3. temperaturein the morning was warmed
  4. concentrationThe reaction was concentrated in vacuo
  5. filtrationfiltered
  6. custompurified by RPHPLC, 20-70% ACN/H2O with 0.1% TFA
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ebcc140ade1846b18ed02321e0fea3af
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090593B2

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