Methylamine → HCID 69482178, compound

HRID 2364553Notes

Reaction equation

HRID 2364553 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:32])=[C:14]([C:28]([O:30]C)=O)[C:15](=[O:27])[N:16]3[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:33][NH2:34]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:32])=[C:14]([C:28]([NH:34][CH3:33])=[O:30])[C:15](=[O:27])[N:16]3[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 69480433HCID 69480433, compound

Product 1

HCID 69482178HCID 69482178, compoundYield 97%

Procedure

In a similar manner to that described in example 196, from methyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[4-(methyloxy)phenyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (50 mg, 0.115 mmol) and methylamine was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-methyl-1-[4-(methyloxy)phenyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (48 mg, 97% yield) as a white solid. 1H NMR (CDCl3) δ 9.96 (s, 1 H), 8.48 (s, 1 H), 7.11-7.05 (m, 4 H), 7.01-6.98 (m, 4 H), 6.77 (s, 1 H), 3.92 (s, 2 H), 3.87 (s, 3 H), 2.95 (d, J=4.8 Hz, 3 H); HRMS m/z calcd for C24H21FN3O4: 434.1511 Found: 434.1512.

Sources & evidence

ORD record
ord-b046921540a144c79cd3af9ed8803b53
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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