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

HRID 598461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598461
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

Komponenten

9

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-bd2ea45aebbe4056ad24618ad6dfc0fd
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897623B2

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