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

HRID 2364305Notes

Reaction equation

HRID 2364305 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:26])=[C:14]([C:21](OCC)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:27][CH2:28][CH:29]([OH:32])[CH2:30][OH:31]>>[OH:32][CH:29]([CH2:30][OH:31])[CH2:28][NH:27][C:21]([C:14]1[C:15](=[O:20])[N:16]([CH3:19])[C:17]2[C:12]([C:13]=1[OH:26])=[N:11][CH:10]=[C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH:18]=2)=[O:22]

Participants

3

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69480966N-(2,3-dihydroxypropyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 91%

Procedure

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (10 mg, 0.028 mmol) described in example 92 and 3-amino-1,2-propanediol (36 mg, 0.393 mmol), was prepared N-(2,3-dihydroxypropyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (10 mg, 91% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.49 (br s, 1 H), 8.56 (s, 1 H), 7.39 (s, 1 H), 7.17-7.13 (m, 2 H), 7.04-6.99 (m, 2 H), 4.13 (s, 2 H), 3.92 (m, 1 H), 3.67-3.54 (m, 4 H), 3.57 (s, 3 H).

Sources & evidence

ORD record
ord-66edb70112b0492ab2642446ed7c2bb7
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…