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

HRID 2364482Notes

Reaction equation

HRID 2364482 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][C@@H: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][C@@H: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 80307L-AlaninolHCID 69482202HCID 69482202, compound

Product 1

HCID 694804237-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1 S)-2-hydroxy-1-methylethyl]-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 85%

Procedure

In a manner similar to that described in 321, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxylate (38 mg, 0.089 mmol) and (2S)-2-amino-1-propanol (0.05 mL) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1 S)-2-hydroxy-1-methylethyl]-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide (34 mg, 85% yield) as a white solid. 1H NMR (DMSO-d6) δ 10.07 (d, J=8 Hz, 1 H), 8.58 (s, 1 H), 8.19 (s, 1 H), 7.37-7.33 (m, 2 H), 7.14-7.09 (m, 2 H), 5.19 (m, 2 H), 5.01 (m, 1 H), 4.12 (s, 2 H), 4.03 (m, 1 H), 3.43 (m, 2 H), 1.16 (d, J=6.8 Hz, 3 H); HRMS m/z calcd for C21H20F4N3O4: 454.1385. Found: 454.1391.

Sources & evidence

ORD record
ord-c40f55d7cda849748ab26f79eb6b404f
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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