4-Chloro-6,7-dimethoxyquinoline → 4-Benzoyl-1-(4-(6,7-dimethoxyquinolin-4-yloxy)-3 fluorophenyl)pyrrolidin-2-one

HRID 1993387노트

반응식

HRID 1993387 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:16]([CH:24]1[CH2:28][N:27]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([F:36])[CH:30]=2)[C:26](=[O:37])[CH2:25]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.O1CCOCC1.CCOC(C)=O>[C:16]([CH:24]1[CH2:28][N:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][CH:3]=3)=[C:31]([F:36])[CH:30]=2)[C:26](=[O:37])[CH2:25]1)(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

6

반응물 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 574454064-Benzoyl-1-(3-fluoro-4-hydroxyphenyl)pyrrolidin-2-one

생성물 1

HCID 118577274-Benzoyl-1-(4-(6,7-dimethoxyquinolin-4-yloxy)-3 fluorophenyl)pyrrolidin-2-one

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
160 °C

실험 절차

A mixture of 4-chloro-6,7-dimethoxyquinoline (0.38 g, 1.67 mmol), 4-benzoyl-1-(3-fluoro-4-hydroxyphenyl)pyrrolidin-2-one (Step 3, 0.40 g, 1.67 mmol) and DMAP (0.204 g, 1.67 mmol) in 4 mL of dioxane (in a microwave tube) was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 160° C. for 1 h. The mixture was cooled to RT and diluted with 50 mL of EtOAc. The solution was washed with 20 mL of satd. NaHCO3 followed by 20 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (50% to 100% EtOAc in hexanes then to 5% MeOH/EtOAc) to provide a white solid. MS (ESI pos. ion) m/z: 487.4 (M+H). Calc'd Exact Mass for C28H23FN2O5: 486.49.

후처리

  1. temperatureThe mixture was cooled to RT
  2. washThe solution was washed with 20 mL of satd
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (50% to 100% EtOAc in hexanes
  6. customto 5% MeOH/EtOAc) to provide a white solid

출처 및 근거

ORD 기록
ord-61631bea82a142edb4401d120490eb7d
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652009B2

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