1,1'-Carbonyldiimidazole → 2-[[(2S)-1-[(4-Methoxy-2,6-dimethyl-phenyl)sulfonyl]-1,2,3,4-tetrahydro-quinolin-2-yl]-methoxy]-1-(3-pyridin-4-yl-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridin-5-yl)-ethanone

HRID 2388690ノート

反応式

HRID 2388690 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][C@H:14]2[CH2:23][O:24][CH2:25][C:26](O)=[O:27])(=[O:12])=[O:11])=[C:5]([CH3:29])[CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[N:42]1[CH:47]=[CH:46][C:45]([C:48]2[C:52]3[CH2:53][NH:54][CH2:55][CH2:56][C:51]=3[O:50][N:49]=2)=[CH:44][CH:43]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:29])[C:6]([S:10]([N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][C@H:14]2[CH2:23][O:24][CH2:25][C:26]([N:54]2[CH2:55][CH2:56][C:51]3[O:50][N:49]=[C:48]([C:45]4[CH:46]=[CH:47][N:42]=[CH:43][CH:44]=4)[C:52]=3[CH2:53]2)=[O:27])(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

参加物

6

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 46222615(S)-2-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetic AcidHCID 579486603-(Pyridin-4-yl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine

生成物 1

HCID 579486592-[[(2S)-1-[(4-Methoxy-2,6-dimethyl-phenyl)sulfonyl]-1,2,3,4-tetrahydro-quinolin-2-yl]-methoxy]-1-(3-pyridin-4-yl-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridin-5-yl)-ethanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

(S)-2-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetic acid (AC31) (0.13 g, 0.31 mmol) was dissolved in dichloromethane (4 ml) and 1,1′-carbonyldiimidazole (53 mg, 0.325 mmol) was added. After the mixture had been stirred at room temperature for 1 h, 3-(pyridin-4-yl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine (AM5) (62 mg, 0.31 mmol) in dichloromethane (4 ml) was added and the mixture was stirred at room temperature overnight. Saturated sodium hydrogen carbonate solution was added to the reaction mixture, the aqueous phase was extracted with dichloromethane (2×) and the combined organic phases were washed with saturated sodium chloride solution, dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica) with ethyl acetate/hexane 20/1. Yield: 0.13 g (77%). MS, Rt=4.8 min, m/z=603.1 [MH]+

後処理

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe aqueous phase was extracted with dichloromethane (2×)
  3. washthe combined organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (silica) with ethyl acetate/hexane 20/1

出典と根拠

ORDレコード
ord-0ffca944c2984eea8066d935e5e9a369
出典データセット
uspto-grants-2012_09
特許番号
US08268814B2

反応ノート

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