Trifluoroacetic acid → N-{4-[4-(Cyclopropylureido)3-fluorophenoxy]-7-methoxyquinolin-6-yl}acetamide

HRID 853392Notes

Reaction equation

HRID 853392 reaction equation
C(O[C:9](=[O:38])[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:31]([NH:33][CH:34]2[CH2:36][CH2:35]2)=[O:32])=[C:26]([F:37])[CH:25]=1)C1C=CC=CC=1.F[C:40](F)(F)C(O)=O>C1(SC)C=CC=CC=1>[CH:34]1([NH:33][C:31](=[O:32])[NH:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][C:14]3[C:13]4[C:18](=[CH:19][C:20]([O:21][CH3:22])=[C:11]([NH:10][C:9](=[O:38])[CH3:40])[CH:12]=4)[N:17]=[CH:16][CH:15]=3)=[CH:25][C:26]=2[F:37])[CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58931295{4-[4-(Cyclopropylureido)-3-fluorophenoxy]-7-methoxyquinolin-6-yl]carbamic acid benzyl ester

Product 1

HCID 58931413N-{4-[4-(Cyclopropylureido)3-fluorophenoxy]-7-methoxyquinolin-6-yl}acetamide

Reagents, catalysts & solvents 1

HCID 7520ThioanisoleSolvent

Procedure

{4-[4-(Cyclopropylureido)-3-fluorophenoxy]-7-methoxyquinolin-6-yl}carbamic acid benzyl ester (11 mg) was heated and stirred in a mixture of trifluoroacetic acid (3 ml) and thioanisole (0.5 ml) at 60° C., in the same manner as Example 264, for debenzylation. The resulting amino compound was acetylated in the same manner as Example 265 to obtain the title compound (2 mg) as a solid.

Sources & evidence

ORD record
ord-299dac9fe9e44011b04fc9175a8124f7
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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