Methylamine → HCID 69481082, compound

HRID 2364436Notes

Reaction equation

HRID 2364436 reaction equation
[CH:1]1([NH:4][C:5](=[O:32])[CH2:6][N:7]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH:15]=3)[C:10]([OH:25])=[C:9]([C:26]([O:28]CC)=O)[C:8]2=[O:31])[CH2:3][CH2:2]1.[CH3:33][NH2:34]>>[CH:1]1([NH:4][C:5](=[O:32])[CH2:6][N:7]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)[CH:15]=3)[C:10]([OH:25])=[C:9]([C:26]([NH:34][CH3:33])=[O:28])[C:8]2=[O:31])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 69482711HCID 69482711, compound

Product 1

HCID 69481082HCID 69481082, compound

Procedure

This compound was prepared from ethyl 1-[2-(cyclopropylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and methanolic methylamine employing methods similar to those described in Example 245. The crude material was triturated with a mixture of MeOH and 1N HCl to afford the product as a white solid: 1H NMR (d6-DMSO) δ 9.99 (1H, d, J=5 Hz), 8.53 (1H, s), 8.23 (1H, d, J=4 Hz), 7.74 (1H, s), 7.32 (2H, dd, J=8.6, 5.7 Hz), 7.11 (2H, t, J˜9 Hz), 4.79 (2H, s), 4.13 (2H, s), 2.88 (3H, d, J=5 Hz), 2.57 (1H, m), 0.59 (2H, m), 0.34 (2H, m); HRMS calcd for C22H21FN4O4+H+: 425.1625. Found: 425.1623.

Workup

  1. customThe crude material was triturated with a mixture of MeOH and 1N HCl

Sources & evidence

ORD record
ord-05da387514744737b3de1215d6db3ac5
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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