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

HRID 2364325Notes

Reaction equation

HRID 2364325 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][CH:32]([CH3:35])[CH2:33][OH:34]>>[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][CH:32]([CH3:35])[CH2:33][OH:34])=[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

Participants

3

Reactant 2

HCID 51262-AminopropanolHCID 69482202HCID 69482202, compound

Product 1

HCID 694821997-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 65%

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 (20 mg, 0.050mmol) and 2-amino-1-propanol (0.05 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide(15 mg, 65% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 9.98 (d, J=7.6 Hz, 1 H), 8.58 (s, 1 H), 7.37 (s, 1 H), 7.15-7.12 (m, 2 H), 7.04-6.99 (m, 2 H), 4.82 (br s, 2 H), 4.26 (m, 1 H), 4.13 (s, 2 H), 3.78 (dd, J=10.8, 4 Hz, 1 H), 3.67 (dd, J=10.8, 6, 1 H), 1.30 (d, J=6.8 Hz, 3 H); MS m/z 454 M+1).

Sources & evidence

ORD record
ord-232df41e22354e27892f9f305d307e34
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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