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

HRID 1645093ノート

反応式

HRID 1645093 の反応式
[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

参加物

9

反応物 7

HCID 962WaterHCID 6228DimethylformamideHCID 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 865836084-chloro-3-((trifluoromethyl)phenyl)-N'-(4-(3-carbomethoxyphenyl)carboxyaminophenyl)urea収率 43%

試薬・触媒・溶媒 1

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-7e333621786b4ae18a97e6cb9221290b
出典データセット
uspto-grants-2012_02
特許番号
US08124630B2

反応ノート

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