Pyridine → 1,1-Dimethylethyl 4-[4-(4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl)-2-thiazolyl]-1-piperidinecarboxylate

HRID 1802324노트

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HRID 1802324 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[S:16])[NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:18][C:19]([C:21]1[CH2:25][CH:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])[O:23][N:22]=1)=O.N1C=CC=CC=1>C(O)C>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH:24]1[O:23][N:22]=[C:21]([C:19]2[N:15]=[C:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]3)[S:16][CH:18]=2)[CH2:25]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 866476752-Chloro-1-[4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl]ethanone2회

생성물 1

HCID 666335001,1-Dimethylethyl 4-[4-(4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl)-2-thiazolyl]-1-piperidinecarboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
77 °C

실험 절차

To a solution of 1-tert-butoxycarbonylpiperidine-4-carbothioamide (1 g, 4.10 mmol) in ethanol (10 mL) was added 2-chloro-1-[4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl]ethanone (i.e. the product of Step A) (0.99 g) followed by pyridine (0.34 mL, 4.10 mmol). The reaction mixture was heated at 77° C. for 3 h, and then stirred at room temperature overnight. Ethanol was removed from the reaction mixture, and the remaining residue was diluted with ethyl acetate (50 mL). The organic layer was separated, washed with water, saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated under reduced pressure. The resulting oil was purified by column chromatography on silica gel to provide the title compound as a pale yellow sticky oil (1.11 g).

후처리

  1. customEthanol was removed from the reaction mixture
  2. additionthe remaining residue was diluted with ethyl acetate (50 mL)
  3. customThe organic layer was separated
  4. washwashed with water, saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oil was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-33fa61845470427fb193f2c7c0f39590
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349870B2

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