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

HRID 2364259Notes

Reaction equation

HRID 2364259 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH:19]=3)[C:14]([OH:29])=[C:13]([C:30](OC)=[O:31])[C:12]2=[O:34])=[CH:7][CH:6]=1)=[O:4].[NH2:36][CH2:37][CH2:38][CH2:39][N:40]1[CH2:44][CH2:43][CH2:42][C:41]1=[O:45]>CO>[CH3:1][N:2]([CH3:35])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH:19]=3)[C:14]([OH:29])=[C:13]([C:30]([NH:36][CH2:37][CH2:38][CH2:39][N:40]3[CH2:44][CH2:43][CH2:42][C:41]3=[O:45])=[O:31])[C:12]2=[O:34])=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 69480958HCID 69480958, compound

Product 1

HCID 694822901-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner to that described in example 196, from methyl 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.0421 mmol), 1-(3-aminopropyl)-2-pyrrolidinone (0.05 mL), and methanol (2 mL), was prepared 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (20 mg, 80% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.04 (t, J=6 Hz, 1 H), 8.51 (d, J=1.6 Hz, 1 H), 7.65 (d, J=8.4 Hz, 2 H), 7.28 (d, J==8.4 Hz, 2 H), 7.03-6.99 (m, 2 H), 6.96-6.91 (m, 2 H), 6.79 (d, J=1.6 Hz, 1 H), 3.94 (s, 2 H), 3.45-3.33 (m, 6 H), 3.16 (s, 3 H), 3.06 (s, 3 H), 2.36 (t, J=8 Hz, 2 H), 2.05-1.97 (m, 2 H), 1.87-1.80 (m, 2 H); MS m/z 586 (M+1).

Sources & evidence

ORD record
ord-cc9e3417d34d463098452a16d79c6380
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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