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

HRID 2364357Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:21])=[C:5]([C:22](OCC)=[O:23])[C:4]1=[O:27])[CH3:2].[NH2:28][CH:29]([CH3:32])[CH2:30][OH:31]>>[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:21])=[C:5]([C:22]([NH:28][CH:29]([CH3:32])[CH2:30][OH:31])=[O:23])[C:4]1=[O:27])[CH3:2]

Participants

Reactant 2

HCID 51262-Aminopropanol

HCID 69482004HCID 69482004, compound

Product 1

HCID 694810141-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 66%

Procedure

In a similar manner to that described in example 196, from ethyl 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.081 mmol) and 2-amino-1-propanol (0.052 mL, 0.648 mmol) was prepared 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (21 mg, 66% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.34 (d, J=7.2 Hz, 1 H), 8.55 (s, 1 H), 7.36 (s, 1 H), 7.18-7.14 (m, 2 H), 7.05-7.01 (m, 2 H), 4.28 (m, 1 H), 4.21-4.14 (m, 4 H), 3.79 (dd, J=10.8, 3.6 Hz, 1 H), 3.68 (dd, J=10.8, 6 Hz, 1 H), 1.32 (d, J=6.8 Hz, 3 H), 1.24 (t, J=6.8 Hz, 3 H); HRMS m/z calcd for C21H23FN3O4: 400.1667. Found: 400.1674.

Sources & evidence

ORD record: ord-6ff460cec4a041c1ac522852914d3514
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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