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

HRID 598461노트

반응식

HRID 598461 반응식
ClC1(N)C=CC([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])=CC1.[C:23]([O:34][CH3:35])(=[O:33])[C:24]1[CH:32]=[CH:31][CH:30]=[C:26]([C:27]([O-])=O)[CH:25]=1.[CH:36]1[CH:37]=C[C:39]2N(O)N=[N:42][C:40]=2[CH:41]=1.[OH2:46].CN1C[CH2:52][O:51]CC1.CCN=C=NCCCN(C)C.[ClH:65]>CN(C=O)C.CCOC(C)=O>[Cl:65][C:27]1([C:26]2[CH:30]=[CH:31][CH:32]=[C:24]([C:23]([O:34][CH3:35])=[O:33])[CH:25]=2)[CH:37]=[CH:36][C:41]([NH:10][C:9]([NH:8][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:19])([F:20])[F:21])=[O:11])=[C:40]([NH:42][C:52]([OH:51])=[O:46])[CH2:39]1

참가 물질

9

반응물 6

HCID 962WaterHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69512791,3-Benzenedicarboxylic acid, monomethyl esterHCID 865836094-chloro-3-((trifluoromethyl)phenyl)-N'-(4-aminophenyl)urea

생성물 1

HCID 866180784-chloro-3-((trifluoromethyl)phenyl)-N-(4-(3-methoxycarbonylphenyl)carboxyaminophenyl) urea수율 43%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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

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

출처 및 근거

ORD 기록
ord-bd2ea45aebbe4056ad24618ad6dfc0fd
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897623B2

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