Water → 4-(4-amino-2-fluorophenoxy)-7-methoxy-N-methylquinoline-6-carboxamide

HRID 1873700Notes

Reaction equation

HRID 1873700 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([C:17](OC)=[O:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4]([F:25])[CH:3]=1.O.[CH3:27][N:28]1CCCCC1=O>>[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([C:17]([NH:28][CH3:27])=[O:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4]([F:25])[CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 13603N-Methyl-2-piperidoneHCID 66916282Methyl 4-(4-amino-2-fluorophenoxy)-7-methoxyquinoline-6-carboxylate

Product 1

HCID 669163504-(4-amino-2-fluorophenoxy)-7-methoxy-N-methylquinoline-6-carboxamideYield 64%

Conditions

Temperature
40 °C

Procedure

Compound 39b (100 mg) was dissolved in N-methylpiperidin-2-one (250 μL), and 40% methylaminemethanol solution (250 μL) was added thereto, followed by stirring at 40° C. for 16 hours. Subseuqntly, water was added to the reaction mixture, and the precipitate was filtrated, to thereby yield compound 46a (63.7 mg, yield: 64%).

Workup

  1. filtrationthe precipitate was filtrated

Sources & evidence

ORD record
ord-37178aa6bc0d4104b2c01528782603fd
Source dataset
uspto-grants-2012_11
Patent number
US08304427B2

Reaction notes

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