Ethanolamine → HCID 69482575, compound

HRID 2364314Notes

Reaction equation

HRID 2364314 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:24])=[C:14]([C:20](OC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[C:4]([C:25]([F:28])([F:27])[F:26])[CH:3]=1.[CH2:29]([CH2:31][NH2:32])[OH:30]>>[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:24])=[C:14]([C:20]([NH:32][CH2:31][CH2:29][OH:30])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[C:4]([C:25]([F:28])([F:26])[F:27])[CH:3]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69482880HCID 69482880, compound

Product 1

HCID 69482575HCID 69482575, compound

Procedure

This compound was prepared from methyl 7-{[4-fluoro-2-(trifluoromethyl)phenyl]methyl}-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and ethanolamine employing methods similar to those described in Example 245 and was purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase). The product was obtained as an off-white solid: 1H NMR (d6-DMSO) δ 11.70 (1H, br), 10.33 (1H, m), 8.49 (1H, s), 7.70 (1H, d, J=9 Hz), 7.56 (2H, m), 7.32 (1H, s), 4.91 (1H, br t), 4.32 (2H, s), 3.56 (2H, m), 3.45 (2H, m); ES− MS: 424 (M−1, 100).

Workup

  1. customwas purified by reverse phase preparative HPLC (C-18 stationary phase; 10-100% CH3CN/water/0.1% formic acid mobile phase)
  2. customThe product was obtained as an off-white solid

Sources & evidence

ORD record
ord-568eb97feafd4a65b242accaa6a32548
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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