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1-Propanol → (4-Propoxy-3-(trifluoromethyl)phenyl)(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-yl)methanone

HRID 2204242
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HRID 2204242 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][C:13]3([O:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[N:17]4[CH:25]=[CH:26][CH:27]=[C:16]34)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29].[CH2:32]([OH:35])[CH2:33][CH3:34].[H-].[Na+]>C(#N)C>[CH2:32]([O:35][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][C:13]3([O:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[N:17]4[CH:25]=[CH:26][CH:27]=[C:16]34)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[C:28]([F:30])([F:29])[F:31])[CH2:33][CH3:34]
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참가 물질

5

반응물 3

HCID 10311-PropanolHCID 24758Sodium hydrideHCID 58550866(4-Fluoro-3-(trifluoromethyl)phenyl)(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-yl)methanone

생성물 1

HCID 58550798(4-Propoxy-3-(trifluoromethyl)phenyl)(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-yl)methanone

시약·촉매·용매 1

HCID 6342Acetonitrile
용매

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온도
70 °C

실험 절차

(4-Fluoro-3-(trifluoromethyl)phenyl)(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)methanone (22 mg, 0.051 mmol), nPrOH (12 μL, 0.15 mmol), and NaH (60%, 6.1 mg, 0.15 mmol) were combined in acetonitrile (1 mL) and the reaction mixture was heated at 70° C. for 1 h. The reaction mixture was filtered and purified by reverse phase HPLC to provide (4-propoxy-3-(trifluoromethyl)phenyl)(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)methanone. ESI-MS m/z calc. 470.2, found 471.2 (M−1)−; Retention time: 2.83 minutes (4 min run).

후처리

  1. filtrationThe reaction mixture was filtered
  2. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-301a8e636fbf4ad2b0a7638ad4123415
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365588B2

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