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 2388690노트

반응식

HRID 2388690 반응식
[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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(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]+

후처리

  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

출처 및 근거

ORD 기록
ord-0ffca944c2984eea8066d935e5e9a369
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268814B2

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