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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-N-(4-((7-(2-hydroxypropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 2277392
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HRID 2277392 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C@H:19]([OH:21])[CH3:20])=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:24][N:25]1[C:29]([CH3:30])=[C:28]([C:31](O)=[O:32])[C:27](=[O:34])[N:26]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.O>[OH:21][C@H:19]([CH3:20])[CH2:18][O:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:31]([C:28]4[C:27](=[O:34])[N:26]([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)[N:25]([CH3:24])[C:29]=4[CH3:30])=[O:32])=[CH:23][CH:22]=3)=[CH:8][CH:9]=[N:10]2)=[CH:15][CH:14]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 246564Antipyric acidHCID 68193946(R)-1-((4-(4-aminophenoxy)quinolin-7-yl)oxy)propan-2-ol

생성물 1

HCID 60172730(R)-N-(4-((7-(2-hydroxypropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide수율 14.3%

시약·촉매·용매

2
HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
43 °C

실험 절차

To a solution of (R)-1-((4-(4-aminophenoxy)quinolin-7-yl)oxy)propan-2-ol (2.5 g, 11.9 mmol), 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carb oxylic acid (2.0 g, 8.6 mmol) and HOAT (0.2 g, 1.6 mmol) in DCM (35 mL) was added EDCI (1.9 g, 9.7 mmol). The reaction mixture was stirred at 43° C. for 12 hours, then cooled to room temperature and diluted with a mixture of DCM and H2O (50 mL/50 mL). The organic phase was separated, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a column chromatography on silica gel (EtOAc) to afford the title compound as a yellow solid (0.6 g, 14.3%).

후처리

  1. temperaturecooled to room temperature
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a column chromatography on silica gel (EtOAc)

출처 및 근거

ORD 기록
ord-dbe2299a314547f489025eb3e15eb38b
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133162B2

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