Sodium Methoxide → (3-(4-(1H-pyrazol-1-yl)benzyl)-4-chloro-2-methoxyquinolin-6-yl)(4-chlorophenyl)(pyridin-3-yl)methanol

HRID 926605노트

반응식

HRID 926605 반응식
[N:1]1([C:6]2[CH:39]=[CH:38][C:9]([CH2:10][C:11]3[C:12](Cl)=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([C:22]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[OH:23])=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[CH3:40][O-:41].[Na+]>C1(C)C=CC=CC=1>[N:1]1([C:6]2[CH:39]=[CH:38][C:9]([CH2:10][C:11]3[C:12]([O:41][CH3:40])=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([C:22]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[OH:23])=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 74220747(3-(4-(1H-Pyrazol-1-yl)benzyl)-2,4-dichloroquinolin-6-yl)(4-chlorophenyl)(pyridin-3-yl)methanol2회

생성물 1

HCID 118007124(3-(4-(1H-pyrazol-1-yl)benzyl)-4-chloro-2-methoxyquinolin-6-yl)(4-chlorophenyl)(pyridin-3-yl)methanol

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
105 °C

실험 절차

(3-(4-(1H-Pyrazol-1-yl)benzyl)-2,4-dichloroquinolin-6-yl)(4-chlorophenyl)(pyridin-3-yl)methanol (61.9 mg, 0.108 mmol, Intermediate 37) and sodium methoxide (0.0313 g, 0.579 mmol) were charged to a microwave vial with dry toluene (0.57 mL) and heated to 105° C. for 4 hours. The mixture was allowed to cool to room temperature, then filtered through Celite® and rinsed with dichloromethane. The filtrate was concentrated to dryness and purified by reverse-phase chromatography (acetonitrile/H2O+0.05% TFA). The isolated product fractions were basified with saturated aqueous sodium bicarbonate, extracted with DCM, dried (Na2SO4), filtered, and concentrated to dryness to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 8.50 (s, 1H), 8.46 (d, J=4.0 Hz, 1H), 8.02 (d, J=1.9 Hz, 1H), 7.84 (dd, J=2.5, 0.5 Hz, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.68-7.63 (m, 2H), 7.56-7.52 (m, 2H), 7.49 (dd, J=8.8, 2.2 Hz, 1H), 7.33 (dd, J=6.5, 4.6 Hz, 2H), 7.31-7.27 (m, 2H), 7.25-7.20 (m, 3H), 6.42 (dd, J=2.4, 1.8 Hz, 1H), 4.29 (s, 2H), 4.08 (s, 3H); MS m/e 567.2 [M+H]+.

후처리

  1. temperatureto cool to room temperature
  2. filtrationfiltered through Celite®
  3. washrinsed with dichloromethane
  4. concentrationThe filtrate was concentrated to dryness
  5. custompurified by reverse-phase chromatography (acetonitrile/H2O+0.05% TFA)
  6. extractionextracted with DCM
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-d300daa2c00342e79b4ae79ef35eda54
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284308B2

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