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

HRID 2364243Notes

Reaction equation

HRID 2364243 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([OH:26])=[C:10]([C:27](OCC)=[O:28])[C:9]2=[O:32])=[CH:4][CH:3]=1.[CH3:33][O:34][CH2:35][CH2:36][NH2:37]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([OH:26])=[C:10]([C:27]([NH:37][CH2:36][CH2:35][O:34][CH3:33])=[O:28])[C:9]2=[O:32])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 59799019Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694821561-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (21 mg, 0.048 mmol) was dissolved in ethanol (1 mL) and [2-(methyloxy)ethyl]amine (0.05 mL) was added. This solution was heated in a microwave at 140° C. for 20 minutes. The resulting suspension was concentrated under reduced pressure and 1 N hydrochloric acid was added to bring the mixture to a pH of 3. The resulting white solid was collected by vacuum filtration to yield 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (19.8 mg, 86%). 1H NMR (CDCl3) δ 10.07 (m, 1 H), 8.52 (s, 1 H), 7.30-7.28 (m, 2 H), 7.22-7.18 (m, 2 H), 7.02-6.92 (m, 4 H), 6.70 (s, 1 H), 3.95 (s, 2 H), 3.65-3.60 (m, 2 H), 3.55-3.52 (m, 2 H), 3.33 (s, 3 H); MS m/z 459 (M+23).

Workup

  1. concentrationThe resulting suspension was concentrated under reduced pressure and 1 N hydrochloric acid
  2. additionwas added
  3. filtrationThe resulting white solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-bd8cc63517e246b6b3fdd82ca434c8bf
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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