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 75184ノート

反応式

HRID 75184 の反応式
[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

参加物

5

反応物 3

HCID 1049PyridineHCID 866744762-Chloro-1-(5-(2,6-difluorophenyl)-4,5-dihydroisoxazol-3-yl)ethan-1-one2 回HCID 86674477HCID 86674477、化合物2 回

生成物 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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c50cd64e2ba84c46a2ad19021257f757
出典データセット
uspto-grants-2014_09
特許番号
US08835427B2

反応ノート

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