Trifluoroacetic acid → (R)-5-(2-chloro-6-fluorophenyl)-3-(6-(piperidin-3-yloxy)pyrazin-2-yl)-1H-indole bis(2,2,2-trifluoroacetate)

HRID 1529320노트

반응식

HRID 1529320 반응식
[Cl: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)[NH:14][CH:13]=[C:12]2[C:18]1[N:23]=[C:22]([O:24][C@@H:25]2[CH2:30][CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]2)[CH:21]=[N:20][CH:19]=1.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>C(Cl)Cl>[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[Cl: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)[NH:14][CH:13]=[C:12]2[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([O:24][C@@H:25]2[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]2)[N:23]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67960707(R)-tert-butyl 3-(6-(5-(2-chloro-6-fluorophenyl)-1H-indol-3-yl)pyrazin-2-yloxy)piperidine-1-carboxylate

생성물 1

HCID 86709771(R)-5-(2-chloro-6-fluorophenyl)-3-(6-(piperidin-3-yloxy)pyrazin-2-yl)-1H-indole bis(2,2,2-trifluoroacetate)

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (R)-tert-butyl 3-(6-(5-(2-chloro-6-fluorophenyl)-1H-indol-3-yl)pyrazin-2-yloxy)piperidine-1-carboxylate (0.077 g, 0.147 mmol) in 1.5 mL DCM was added TFA (0.170 mL, 2.208 mmol). After 30 min, the reaction was concentrated in vacuo, taken up in DMSO, and purified by RPHPLC, 10-100% ACN/H2O with 0.1% TFA; product-containing fractions were combined and concentrated in vacuo to give (R)-5-(2-chloro-6-fluorophenyl)-3-(6-(piperidin-3-yloxy)pyrazin-2-yl)-1H-indole bis(2,2,2-trifluoroacetate) as an orange solid. MS (ESI, pos. ion) m/z: 423 (M+1).

후처리

  1. concentrationthe reaction was concentrated in vacuo
  2. custompurified by RPHPLC, 10-100% ACN/H2O with 0.1% TFA
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-cd6459ea45a54c91862ce327ef293f17
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090593B2

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