Methylamine → HCID 69482046, compound

HRID 2364432Notes

Reaction equation

HRID 2364432 reaction equation
[C:1]([N:4]([CH3:32])[CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:15]=2)[C:10]([OH:25])=[C:9]([C:26]([O:28]CC)=O)[C:8]1=[O:31])(=[O:3])[CH3:2].[CH3:33][NH2:34]>C(O)C>[C:1]([N:4]([CH3:32])[CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:15]=2)[C:10]([OH:25])=[C:9]([C:26]([NH:34][CH3:33])=[O:28])[C:8]1=[O:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 69481486HCID 69481486, compound

Product 1

HCID 69482046HCID 69482046, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This compound was prepared from ethyl 1-{2-[acetyl(methyl)amino]ethyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and methylamine in ethanol using methods similar to Example 574: step 2 to provide an off-white solid: 1H NMR (400 MHz, DMSO-d6 (90° C.) δ ppm 1.80-1.87 (m, 3 H), 2.95 (d, J=4.94 Hz, 6 H), 3.53 (t, J=6.79 Hz, 2 H), 4.18 (s, 2 H), 4.36 (s, 2 H), 7.12 (t, J=8.44 Hz, 2 H), 7.35-7.40 (m, 2 H), 8.05 (s, 1 H), 8.54 (s, 1 H), 10.07 (s, 1 H), 17.05 (br. s., 1 H); ES+ MS: 427 (M+H+).

Workup

  1. customto provide an off-white solid
  2. custom400 MHz, DMSO-d6 (90° C.)

Sources & evidence

ORD record
ord-e21a4b424e7b434db0db3f4573039ab8
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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