Ethanolamine → 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364324Notes

Reaction equation

HRID 2364324 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][OH:34]>>[F:1][C:2]1[CH:3]=[CH:4][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][OH:34])=[O:26])[C:15](=[O:24])[N:16]3[CH2:19][C:20]([F:22])([F:23])[F:21])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69482202HCID 69482202, compound

Product 1

HCID 694815397-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 29%

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 (10 mg, 0.024mmol) and 2-aminoethanol (0.05 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide (3 mg, 29% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (methanol-d4/CDCl3) δ 8.53 (s, 1 H), 7.42 (s, 1 H), 7.13-7.09 (m, 2 H), 7.00-6.96 (m, 2 H), 4.85 (br s, 2 H), 4.10 (s, 2 H), 3.74 (m, 2 H), 3.55 (m, 2 H); MS m/z 440 M+1).

Sources & evidence

ORD record
ord-245b0fa9200942638bf7fac34cee4026
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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