Phenyl cyclopropylcarbamate → {4-[4-(Cyclopropylureido)-3-fluorophenoxy]-7-methoxyquinolin-6-yl]carbamic acid benzyl ester

HRID 387869Notes

Reaction equation

HRID 387869 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2[O:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]([F:31])[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([O:39][C:40](=O)[NH:41][CH:42]2[CH2:44][CH2:43]2)C=CC=CC=1>CS(C)=O>[CH2:1]([O:8][C:9](=[O:32])[NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2[O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:40]([NH:41][CH:42]2[CH2:44][CH2:43]2)=[O:39])=[C:26]([F:31])[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 13648483Phenyl cyclopropylcarbamateHCID 58931409[4-(4-Amino-3-fluorophenoxy)-7-methoxyquinolin-6-yl]carbamic acid benzyl ester

Product 1

HCID 58931295{4-[4-(Cyclopropylureido)-3-fluorophenoxy]-7-methoxyquinolin-6-yl]carbamic acid benzyl esterYield 9.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

[4-(4-Amino-3-fluorophenoxy)-7-methoxyquinolin-6-yl]carbamic acid benzyl ester (100 mg) and cyclopropylcarbamic acid phenyl ester (64 mg) were heated and stirred in dimethylsulfoxide (0.7 ml) at 85° C. for 5 hours and 40 minutes, in the same manner as Example 224, to obtain the title compound (11 mg) as a solid.

Sources & evidence

ORD record
ord-29c6311b35814728bcc3bf5a15fd4f7e
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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