Water → Ethyl 2-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]octahydro-1-oxoimidazo[1,5-a]pyridine-3-carboxylate

HRID 263384노트

반응식

HRID 263384 반응식
C(=O)([O-])[O-].[K+].[K+].Br[CH:8](F)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[Cl:15][C:16]1[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:19]([NH:26][C:27]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][NH:30]2)=[O:28])=[C:18]([F:35])[CH:17]=1.O>C(#N)C.C(OCC)(=O)C>[Cl:15][C:16]1[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:19]([N:26]2[C:27](=[O:28])[CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][N:30]3[CH:8]2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:18]([F:35])[CH:17]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl esterHCID 19037321N-[4-Chloro-2-fluoro-5-(1-methylethoxy)phenyl]piperidine-2-carboxamide

생성물 1

HCID 19037326Ethyl 2-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]octahydro-1-oxoimidazo[1,5-a]pyridine-3-carboxylate수율 21.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of potassium carbonate (724 mg, 5.24 mmol), ethyl bromofluoroacetate (882 mg, 4.76 mmol) and the product of Step A (1.5 g, 4.76 mmol) in acetonitrile (50 mL) was heated at reflux overnight. 100 mL of H2O and 200 mL of ethyl acetate were added to the mixture. The organic layer was separated, dried (MgSO4), filtered, and evaporated under vacuum to dryness. Flash chromatography yielded the title compound of Step B as a white solid (400 mg) m.p. 83°-85° C. 1H NMR δ7.21 (d,1H), 7.18 (d,1H), 4.92 (s,1H), 4.50 (m,1H), 4.16-4.09 (m,2H), 3.29 (m,1H), 2.95 (m,1H), 2.50 (m,1H), 2.10 (m,1H), 1.96 (m,1H), 1.80-1.58 (m,2H), 1.37 (d,6H), 1.35 (t,3H).

후처리

  1. temperatureat reflux overnight
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under vacuum to dryness

출처 및 근거

ORD 기록
ord-9dc2de2cdd334059be8b20ecf8b907cd
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05643855

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