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

HRID 598461ノート

反応式

HRID 598461 の反応式
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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bd2ea45aebbe4056ad24618ad6dfc0fd
出典データセット
uspto-grants-2011_03
特許番号
US07897623B2

反応ノート

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