Water → N-[4-(7-benzyloxy-6-cyanoquinolin-4-yloxy)-2,3-dimethylphenyl]-N'-cyclopropylurea

HRID 388067Notes

Reaction equation

HRID 388067 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.CN(C)C=O.C1([O:16][C:17](=O)[NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]3[C:35]4[C:30](=[CH:31][C:32]([O:38][CH2:39][C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)=[C:33]([C:36]#[N:37])[CH:34]=4)[N:29]=[CH:28][CH:27]=3)=[C:21]([CH3:46])[C:20]=2[CH3:47])C=CC=CC=1.O>C(OCC)(=O)C>[CH2:39]([O:38][C:32]1[CH:31]=[C:30]2[C:35]([C:26]([O:25][C:22]3[CH:23]=[CH:24][C:19]([NH:18][C:17]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:16])=[C:20]([CH3:47])[C:21]=3[CH3:46])=[CH:27][CH:28]=[N:29]2)=[CH:34][C:33]=1[C:36]#[N:37])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 69828CyclopropylamineHCID 67201413(4-(7-Benzyloxy-6-cyano-quinolin-4-yloxy)-2,3-dimethylphenyl)carbamic acid phenyl ester

Product 1

HCID 22936500N-[4-(7-benzyloxy-6-cyanoquinolin-4-yloxy)-2,3-dimethylphenyl]-N'-cyclopropylurea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Cyclopropylamine (1 ml) was added to dimethylformamide (10 ml), and then (4-(7-benzyloxy-6-cyano-quinolin-4-yloxy)-2,3-dimethylphenyl)carbamic acid phenyl ester (1.99 g) was added thereto and the mixture was stirred at room temperature for 10 minutes. Water (30 ml) and ethyl acetate (30 ml) were added, and the precipitated crystals were filtered out and washed with ethyl acetate to obtain the title compound (1660 mg).

Workup

  1. filtrationthe precipitated crystals were filtered out
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-14e9412e41cf4d698135c34c8cd13039
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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