Water → 4-chloro-3-((trifluoromethyl)phenyl)-N'-(4-(3-carbomethoxyphenyl)carboxyaminophenyl)urea

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[Cl:1][C:2]1(N)[CH:7]=[CH:6][C:5]([N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[C:9](=[O:11])[NH2:10])=[CH:4][CH2:3]1.[C:23]([O:34][CH3:35])(=[O:33])[C:24]1[CH:32]=[CH:31][CH:30]=[C:26](C([O-])=O)[CH:25]=1.C1C=CC2N([OH:45])N=NC=2C=1.O.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl.C[N:67]([CH:69]=[O:70])C>CCOC(C)=O>[Cl:1][C:2]1([C:31]2[CH:30]=[CH:26][CH:25]=[C:24]([C:23]([O:34][CH3:35])=[O:33])[CH:32]=2)[CH:7]=[CH:6][C:5]([N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[C:9](=[O:11])[NH2:10])=[C:4]([NH:67][C:69]([OH:70])=[O:45])[CH2:3]1

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To a solution of N-(4-chloro-3-((trifluoromethyl)phenyl)-N′-(4-aminophenyl)urea (Method C1d; 0.050 g, 1.52 mmol), mono-methyl isophthalate (0.25 g, 1.38 mmol), HOBT.H2O (0.41 g, 3.03 mmol) and N-methylmorpholine (0.33 mL, 3.03 mmol) in DMF (8 mL) was added EDCI.HCl (0.29 g, 1.52 mmol). The resulting mixture was stirred at room temp. overnight, diluted with EtOAc (25 mL) and sequentially washed with water (25 mL) and a saturated NaHCO3 solution (25 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The resulting solids were triturated with an EtOAc solution (80% EtOAc/20% hexane) to give N-(4-chloro-3-((trifluoromethyl)phenyl)-N′-(4-(3-methoxycarbonylphenyl)carboxyaminophenyl)urea (0.27 g, 43%): mp 121-122; TLC (80% EtOAc/20% hexane) Rf 0.75.

후처리

washsequentially washed with water (25 mL)
dry with materialThe organic layer was dried (Na2SO4)
concentrationconcentrated under reduced pressure
customThe resulting solids were triturated with an EtOAc solution (80% EtOAc/20% hexane)

출처 및 근거

ORD 기록: ord-e5aa6c48bc814df79ad2320b5daa0559
출처 데이터셋: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08841330B2

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