Tetrahydrofurfurylamine → (+/-)-7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-(tetrahydro-2-furanylmethyl)-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364161Notes

Reaction equation

HRID 2364161 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.[O:26]1[CH2:30][CH2:29][CH2:28][CH:27]1[CH2:31][NH2:32]>>[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]([NH:32][CH2:31][CH:27]4[CH2:28][CH2:29][CH2:30][O:26]4)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 253298TetrahydrofurfurylamineHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 54707849(+/-)-7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-N-(tetrahydro-2-furanylmethyl)-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 (±)-(tetrahydro-2-furanylmethyl)amine employing methods similar to those described in Example 2 and was obtained as a white solid: 1H NMR (d6-DMSO) δ 11.9 (1H, br), 10.60 (1H, br), 8.37 (1H, br), 7.39 (1H, s), 7.30 (2H, m), 7.15 (2H, t, J=8.6 Hz), 4.06 (2H, br s), 3.96 (1H, m), 3.80 (1H, q, J˜7 Hz), 3.64 (1H, q, J˜7 Hz), 3.50-3.20 (2H, m), 2.00-1.52 (4H, m); ES+ MS: 398 (M+H+, 100).

Workup

  1. customwas obtained as a white solid

Sources & evidence

ORD record
ord-df5b89ee4d634b529d937215056acf34
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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