2-Methoxyethylamine → HCID 69480760, compound

HRID 2364231Notes

Reaction equation

HRID 2364231 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:27])=[C:14]([C:24]([O-])=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][CH:20]([CH3:22])[CH3:21])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:28][O:29][CH2:30][CH2:31][NH2:32]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:27])=[C:14]([C:24]([NH:32][CH2:31][CH2:30][O:29][CH3:28])=[O:25])[C:15](=[O:23])[N:16]3[CH2:19][CH:20]([CH3:21])[CH3:22])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 178448688HCID 178448688, compound

Product 1

HCID 69480760HCID 69480760, compoundYield 79%

Procedure

A solution of 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-(2-methylpropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.05 mmol) in 2-methoxyethylamine (1 mL) was heated with a microwave at 140° C. for 20 minutes. The solvent was removed in vacuo and the residue was purified by reverse phase preparative HPLC to give the title compound (17 mg, 79%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.35 (br, 1 H), 8.54 (s, 1 H), 7.25 (s, 1 H), 7.15 (dd, J=8.5, 5.4 Hz, 2 H), 7.03 (t, J=8.5 Hz, 2 H), 4.12 (s, 2 H), 3.97 (br, 2 H), 3.63 (m, 2 H), 3.57 (m, 2 H), 3.39 (s, 3 H), 1.95 (m, 1 H), 0.87 (d, J=6.8 Hz, 6 H); HRMS m/z calcd for C23H27N3O4 (M+H)+ 428.1986, found 428.1977.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-66a361b48d134d87952e8ac1b4639c23
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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