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

HRID 2364158Notes

Reaction equation

HRID 2364158 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([NH2:29])[CH2:28][CH2:27]1>>[CH:26]1([NH:29][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])[CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 54690871N-Cyclopropyl-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 cyclopropylamine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 11.80 (1H, br), 10.35 (1H, br), 8.35 (1H, br), 7.38 (1H, s), 7.30 (2H, m), 7.15 (2H, t, J=8.7 Hz), 4.06 (2H, br s), 2.85 (1H, m), 0.74 (2H, m), 0.51 (2H, m); HRMS calcd for C19H16FN3O3+H+: 354.1254. Found: 354.1255.

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-fed3657d6d6e4a2a908a758dc4e328d1
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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