Diethylamine → 3-(4-(1H-Pyrazol-1-yl)benzyl)-6-bromo-4-chloro-N,N-diethylquinolin-2-amine

HRID 928793노트

반응식

HRID 928793 반응식
[N:1]1([C:6]2[CH:27]=[CH:26][C:9]([CH2:10][C:11]3[C:12](OC)=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([Br:22])=[CH:16][C:15]=4C)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29]>CN(C=O)C.CCOC(C)=O>[N:1]1([C:6]2[CH:27]=[CH:26][C:9]([CH2:10][C:11]3[C:12]([N:30]([CH2:31][CH3:32])[CH2:28][CH3:29])=[N:13][C:14]4[C:19]([C:20]=3[Cl:21])=[CH:18][C:17]([Br:22])=[CH:16][CH:15]=4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

참가 물질

5

반응물 2

HCID 8021DiethylamineHCID 867155993-(4-(1H-Pyrazol-1-yl)benzyl)-6-bromo-4-chloro-2-methoxy-8-methylquinoline2회

생성물 1

HCID 867156263-(4-(1H-Pyrazol-1-yl)benzyl)-6-bromo-4-chloro-N,N-diethylquinolin-2-amine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
115 °C

실험 절차

A mixture of 3-(4-(1H-pyrazol-1-yl)benzyl)-6-bromo-2,4-dichloroquinoline (1.44 g, 3.33 mmol, Intermediate 6, step c) and diethylamine (6.91 mL, 66.5 mmol) in DMF (10 mL) in a sealed tube was heated in a 115° C. oil bath for 23 hours. The mixture was diluted with EtOAc and extracted with water (5×, saturated aqueous NaCl added as needed to achieve phase separation). The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, dry loading, 2-10% EtOAc-Heptane first column, 0-4% EtOAc-Heptane second column) to afford the title compound as a white solid.

후처리

  1. extractionextracted with water (5×, saturated aqueous NaCl added as needed to achieve phase separation)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica gel, dry loading, 2-10% EtOAc-Heptane first column, 0-4% EtOAc-Heptane second column)

출처 및 근거

ORD 기록
ord-079ee80977af4a42995fb0c580a41ff0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290476B2

반응 노트

불러오는 중…