Methylamine → Methyl 4-(4-amino-3-fluorophenoxy)-7-methoxyquinoline-6-carboxylate

HRID 1873706Notes

Reaction equation

HRID 1873706 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](NC)=[O:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4](F)[CH:3]=1.CN.NC1C=CC(OC2C3C(=CC(OC)=C(C(NC)=O)C=3)N=CC=2)=CC=1[F:52].CN1CCC[C:55]1=[O:59]>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([C:17]([O:59][CH3:55])=[O:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:23][C:24]=1[F:52]

Participants

5

Reactant 4

HCID 6329MethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 669163494-(4-amino-3-fluorophenoxy)-7-methoxy-N-methylquinoline-6-carboxamideHCID 669163504-(4-amino-2-fluorophenoxy)-7-methoxy-N-methylquinoline-6-carboxamide

Product 1

HCID 22936312Methyl 4-(4-amino-3-fluorophenoxy)-7-methoxyquinoline-6-carboxylateYield 62%

Procedure

Similar to the synthesis of compound 46a, from compound 49b (50.5 mg), 40% aqueous methylamine solution (500 μL), and N-methylpyrrolidin-2-one (500 μL), compound 49c was yielded (31.2 mg, yield: 62%).

Sources & evidence

ORD record
ord-15c23e1653f7452492643715be2c33c8
Source dataset
uspto-grants-2012_11
Patent number
US08304427B2

Reaction notes

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