Trifluoroacetic acid → 6-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one

HRID 2384907노트

반응식

HRID 2384907 반응식
C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22]4[CH:25]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=5)[S:27][C:21]=4[C:20]3=[O:35])=[CH:15][C:14]=2[O:36][CH3:37])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:9][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22]4[CH:25]=[C:26]([C:28]5[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=5)[S:27][C:21]=4[C:20]3=[O:35])=[CH:15][C:14]=2[O:36][CH3:37])[CH2:11]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 689491773-{4-[2-(4-Chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 689510906-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one수율 78.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Dissolve 3-{4-[2-(4-chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester (924 μmol, 500 mg) in dichloromethane (10 mL), add trifluoroacetic acid (5 mL), and stir the reaction at room temperature for 2 h. Concentrate the material in vacuo and partition the residue between 1N NaOH (10 mL) and CH2Cl2 (15 mL). Separate the organic portion and extract the aqueous portion with CH2Cl2 (3×10 mL). Dry the combined organics over Na2SO4, filter, and concentrate to dryness to afford 320 mg of 6-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one as a white solid.

후처리

  1. customthe reaction at room temperature for 2 h
  2. concentrationConcentrate the material in vacuo
  3. custompartition the residue between 1N NaOH (10 mL) and CH2Cl2 (15 mL)
  4. customSeparate the organic portion
  5. extractionextract the aqueous portion with CH2Cl2 (3×10 mL)
  6. dry with materialDry the combined organics over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate to dryness

출처 및 근거

ORD 기록
ord-eda3feb8156647018d6be5d8e2f3b01c
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263772B2

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