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

HRID 2364359Notes

Reaction equation

HRID 2364359 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:21])=[C:5]([C:22](OCC)=[O:23])[C:4]1=[O:27])[CH3:2].[NH2:28][CH2:29][CH:30]([OH:32])[CH3:31]>>[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)[CH:11]=2)[C:6]([OH:21])=[C:5]([C:22]([NH:28][CH2:29][CH:30]([OH:32])[CH3:31])=[O:23])[C:4]1=[O:27])[CH3:2]

Participants

3

Reactant 2

HCID 41-Amino-2-propanolHCID 69482004HCID 69482004, compound

Product 1

HCID 694810701-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 38%

Procedure

In a similar manner to that described in example 196, from ethyl 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.081 mmol) and 1-amino-2-propanol (0.05 mL) was prepared 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (12 mg, 38% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.49 (s, 1 H), 8.56 (s, 1 H), 7.37 (s, 1 H), 7.18 (m, 2 H), 7.05-7.07 (m, 2 H), 4.23-4.06 (m, 5 H), 3.62 (m, 1 H), 3.38 (m, 1 H), 1.29-1.22 (m, 6 H); HRMS m/z calcd for C21H23FN3O4: 400.1667. Found: 400.1673.

Sources & evidence

ORD record
ord-e47713603c7847c3befeae746a1f1360
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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