Cyclohexylamine → HCID 54676794, compound

HRID 2364154Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][N:10]=2)[NH:5][C:4](=[O:19])[C:3]=1[C:20](OCC)=[O:21].[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>>[CH:25]1([NH:31][C:20]([C:3]2[C:4](=[O:19])[NH:5][C:6]3[C:11]([C:2]=2[OH:1])=[N:10][CH:9]=[C:8]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:7]=3)=[O:21])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Reactant 2

HCID 7965Cyclohexylamine

HCID 54729996HCID 54729996, compound

Product 1

HCID 54676794HCID 54676794, compound

Procedure

This compound was prepared from ethyl 4-hydroxy-2-oxo-7-(phenylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxylate and cyclohexylamine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 11.85 (1H, br), 10.60 (1H, br), 8.33 (1H, br), 7.39 (1H, s), 7.35-7.22 (5H, m), 4.05 (2H, br s), 3.82 (1H, m), 1.85 (2H, m), 1.67 (2H, m), 1.56 (1H, m), 1.38-1.27 (5H, m); HRMS calcd for C22H23N3O3+H+: 378.1810. Found: 378.1822.

Workup

customwas obtained as a white solid

Sources & evidence

ORD record: ord-aee82da7756d4658bb38dae6cc3d73f2
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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