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

HRID 2364322Notes

Reaction equation

HRID 2364322 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:30])=[C:14]([C:25](OCC)=[O:26])[C:15](=[O:24])[N:16]3[CH2:19][C:20]([F:23])([F:22])[F:21])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:31][CH2:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][C:36]1=[O:40]>>[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:30])=[C:14]([C:25]([NH:31][CH2:32][CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][CH2:37][C:36]4=[O:40])=[O:26])[C:15](=[O:24])[N:16]3[CH2:19][C:20]([F:21])([F:22])[F:23])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 69482202HCID 69482202, compound

Product 1

HCID 694804437-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 54%

Procedure

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxylate (23 mg, 0.0542 mmol) and 1-(3-aminopropyl)-2-pyrrolidinone (0.05 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-[3-(2-oxo-1-pyrrolidinyl)propyl]-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide (15 mg, 54% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.05 (br s, 1 H), 8.59 (s, 1 H), 7.38 (s, 1 H), 7.16-7.13 (m, 2 H), 7.05-7.01 (m, 2 H), 4.86 (br s, 2 H), 4.14 (s, 2 H), 3.49-3.37 (m, 6 H), 2.40 (m, 2 H), 2.04 (m, 2 H), 1.87 (m, 2 H); MS m/z 521 (M+1).

Sources & evidence

ORD record
ord-8d32f87b8b264ec28c98b446a0465eb3
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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