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

HRID 2364157Notes

Reaction equation

HRID 2364157 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:25])=[C:14]([C:20]([O:22]CC)=O)[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:26]1([NH2:30])[CH2:29][CH2:28][CH2:27]1>>[CH:26]1([NH:30][C:20]([C:14]2[C:15](=[O:19])[NH:16][C:17]3[C:12]([C:13]=2[OH:25])=[N:11][CH:10]=[C:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:18]=3)=[O:22])[CH2:29][CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 75645CyclobutylamineHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 54713251N-Cyclobutyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and cyclobutylamine employing methods similar to those described in Example 2 and was obtained as an off-white solid: 1H NMR (d6-DMSO) δ 11.90 (1H, br), 10.50 (1H, br), 8.33 (1H, br), 7.39 (1H, br s), 7.31 (2H, m), 7.15 (2H, t, J˜9 Hz), 4.42 (1H, m, J=8 Hz), 4.06 (2H, br s), 2.29 (2H, m), 1.95 (2H, m), 1.71 (2H, m); HRMS calcd for C20H18FN3O3+H+: 368.1410. Found: 368.1410.

Workup

  1. customwas obtained as an off-white solid

Sources & evidence

ORD record
ord-aad682ad26c34a92aab1a1f8f88ec51b
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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