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

HRID 1433729Notes

Reaction equation

HRID 1433729 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-6b5f787ea35443d4b80b664526cae741
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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