Triethylamine → 1-(Isoquinolin-3-yl)-3-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)urea

HRID 571995노트

반응식

HRID 571995 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:20])OC2C=CC=CC=2)[N:2]=1.[CH3:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=[C:30]([C:36]([F:39])([F:38])[F:37])[N:29]=2)[CH2:24][CH2:23]1.C(N(CC)CC)C>CS(C)=O.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12]([NH:35][CH2:34][C:33]2[C:28]([N:25]3[CH2:26][CH2:27][CH:22]([CH3:21])[CH2:23][CH2:24]3)=[N:29][C:30]([C:36]([F:39])([F:37])[F:38])=[CH:31][CH:32]=2)=[O:20])[N:2]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 11817913Phenyl isoquinolin-3-ylcarbamateHCID 58873687(2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine

생성물 1

HCID 712370371-(Isoquinolin-3-yl)-3-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)urea수율 77.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

Phenyl isoquinolin-3-ylcarbamate (100 mg, 0.38 mmol) and (2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine (109 mg, 0.40 mmol) was dissolved in dimethyl sulfoxide. Then triethylamine (0.11 mL, 0.76 mmol) was added to it. The mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The crude was purified by column chromatography to give 1-(isoquinolin-3-yl)-3-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)urea (example compound 21) (130 mg, 77%).

후처리

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-588b6ffedc834ce29ef646cd6e5036db
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029378B2

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