N-Ethylethylenediamine → HCID 69482453, compound

HRID 2364294Notes

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](OCC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:26]([NH:28][CH2:29][CH2:30][NH2:31])[CH3:27]>>[CH2:26]([NH:28][CH2:29][CH2:30][NH:31][C:20]([C:14]1[C:15](=[O:19])[NH:16][C:17]2[C:12]([C:13]=1[OH:25])=[N:11][CH:10]=[C:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:18]=2)=[O:21])[CH3:27]

Participants

Reactant 2

HCID 66071N-Ethylethylenediamine

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

Product 1

HCID 69482453HCID 69482453, compound

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and N-ethylethylenediamine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 11.72 (1H, br s), 10.68 (1H, br s), 8.17 (1H, s), 7.27 (3H, br s), 7.12 (2H, t, J=8.7 Hz), 4.00 (2H, s), 2.62-2.48 (6H, m), 0.99 (3H, t,J =7.1 Hz); HRMS calcd for C20H21FN4O3+H+: 385.1676. Found 385.1685.

Workup

customwas obtained as a white solid

Sources & evidence

ORD record: ord-3a978839cbaf42dcae4759b8d2434b37
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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