Methylamine → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364398Notes

Reaction equation

HRID 2364398 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:29])=[C:14]([C:24]([O:26]CC)=O)[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][CH2:21][OH:22])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:30][NH2:31]>C(O)C>[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:29])=[C:14]([C:24]([NH:31][CH3:30])=[O:26])[C:15](=[O:23])[N:16]3[CH2:19][CH2:20][CH2:21][OH:22])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 69481032HCID 69481032, compound

Product 1

HCID 694804427-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (60 mg, 0.15 mmol) and methylamine (0.11 mL of a 8M solution in ethanol) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(3-hydroxypropyl)-N-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (10 mg, 17% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 9.97 (br s, 1 H), 8.58 (s, 1 H), 7.46 (s, 1 H), 7.17-7.13 (m, 2 H), 7.04-6.99 (m, 2 H), 4.32 (m, 2 H), 4.13 (s, 2 H), 3.49 (m, 2 H), 3.21 (m, 1 H), 3.01 (d, J=4.8 Hz, 3 H), 1.83 (m, 2 H); HRMS m/z calcd for C20H21N3O4F: 386.1516. Found: 386.1517.

Sources & evidence

ORD record
ord-272b1bc005404659bef416a739e5df6c
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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