1-(3-Aminopropyl)-2-pyrrolidinone → 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364323Notes

Reaction equation

HRID 2364323 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24](OCC)=[O:25])[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4].[NH2:30][CH2:31][CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39]>>[CH2:1]([N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:30][CH2:31][CH2:32][CH2:33][N:34]2[CH2:38][CH2:37][CH2:36][C:35]2=[O:39])=[O:25])[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 69482001HCID 69482001, compound

Product 1

HCID 694801881-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 40%

Procedure

In a similar manner to that described in example 196, from ethyl 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.050 mmol) and 1-(3-aminopropyl)-2-pyrrolidinone (0.05 mL) was prepared 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (10 mg, 40% yield) as a yellow oil after purification by reverse phase HPLC. This oil was dissolved in diethyl ether, cooled to 0° C., and sodium ethoxide (0.02 mL of a 1 M solution in ethanol, 0.02 mmol) was added. The resulting white suspension was filtered and the white solids were collected to yield sodium 1-butyl-7-[(4-fluorophenyl)methyl]-2-oxo-3-({[3-(2-oxo-1-pyrrolidinyl)propyl]amino}carbonyl)-1,2-dihydro-1,5-naphthyridin-4-olate (11 mg, 42% overall yield) as a white solid. 1H NMR (CDCl3) δ 10.34 (br s, 1 H), 8.56 (s, 1 H), 7.27 (s, 1 H), 7.19-7.15 (m, 2 H), 7.06-7.02 (m, 2 H), 4.14 (s, 2 H), 4.09 (m, 2 H), 3.48-3.37 (m, 6 H), 2.40 (m, 2 H), 2.04 (m, 2 H), 1.88 (m, 2 H), 1.53 (m, 2 H), 1.34 (m, 2 H), 0.91 (m, 3 H); HRMS m/z calcd for: C27H32N4O4F: 495.2408 Found: 495.2397.

Sources & evidence

ORD record
ord-06b63e4e740347de8d6fc4fd7fbe7045
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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