1-Propanol, 3-amino-2,2-dimethyl- → 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364448Notes

Reaction equation

HRID 2364448 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24](OCC)=[O:25])[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4].[NH2:30][CH2:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34]>>[CH2:1]([N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:30][CH2:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[O:25])[C:6]1=[O:29])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 69482001HCID 69482001, compound

Product 1

HCID 694815081-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 53%

Procedure

In a similar manner to that described in example 196, from ethyl 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.075 mmol) and 3-amino-2,2-dimethyl-1-propanol (0.05 mL) was prepared 1-butyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (18 mg, 53% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.51 (br s, 1 H), 8.56 (s, 1 H), 7.27 (s, 1 H), 7.17-7.13 (m, 2 H), 7.05-7.01 (m, 2 H), 4.14 (s, 2 H), 4.08 (m, 2 H), 3.39 (m, 1 H), 3.30 (m, 2 H), 3.22 (m, 2 H), 1.51 (m, 2 H), 1.33 (m, 2 H), 0.94 (s, 6 H), 0.90 (m, 3 H); MS m/z 456 M+1).

Sources & evidence

ORD record
ord-7c311a4ccb694d2fa1ec33f818549dab
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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