Pyridine → 1,1-dimethylethyl 5-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]hexahydropyrrolo[3,4-c]pyrrol-2(1H)-carboxylate

HRID 75184노트

반응식

HRID 75184 반응식
[NH2:1][C:2](=[S:18])[N:3]1[CH2:7][CH:6]2[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][CH:5]2[CH2:4]1.Cl[CH2:20][C:21]([C:23]1[CH2:27][CH:26]([C:28]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=2[F:35])[O:25][N:24]=1)=O.N1C=CC=CC=1>C(Cl)(Cl)Cl>[F:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([F:34])[C:28]=1[CH:26]1[O:25][N:24]=[C:23]([C:21]2[N:1]=[C:2]([N:3]3[CH2:7][CH:6]4[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:10][CH:5]4[CH2:4]3)[S:18][CH:20]=2)[CH2:27]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 866744762-Chloro-1-(5-(2,6-difluorophenyl)-4,5-dihydroisoxazol-3-yl)ethan-1-one2회HCID 86674477HCID 86674477, 화합물2회

생성물 1

HCID 673413561,1-dimethylethyl 5-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]hexahydropyrrolo[3,4-c]pyrrol-2(1H)-carboxylate

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
90 °C

실험 절차

To a stirred solution of 1,1-dimethylethyl 5-(aminothioxomethyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (i.e. the product of Step A) (0.5 g, 18.42 mmol) in chloroform (20 mL) was added 2-chloro-1-[5-(2,6difluorophenyl)-4,5-dihydroisoxazol-3-yl]ethanone (i.e. the product of Step B) (0.478 g, 18.42 mmol) and pyridine (0.29 g, 37.12 mmol) at room temperature. The reaction mixture was heated at 90° C. for 5 h, cooled to room temperature and concentrated under reduced pressure. The resulting material was dissolved in ethyl acetate (100 mL) and washed with water (100 mL) and saturated aqueous sodium chloride solution (100 mL) and concentrated under reduced pressure. The resulting material was purified by column chromatography (1% methanol/chloroform as eluant) to provide the title product as white solid (0.7 g) melting at 78.9-80.2° C.

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting material was dissolved in ethyl acetate (100 mL)
  4. washwashed with water (100 mL) and saturated aqueous sodium chloride solution (100 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting material was purified by column chromatography (1% methanol/chloroform as eluant)

출처 및 근거

ORD 기록
ord-c50cd64e2ba84c46a2ad19021257f757
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835427B2

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