2-Morpholinoethylamine → HCID 69482055, compound

HRID 2364267Notes

Reaction equation

HRID 2364267 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.[N:29]1([CH2:35][CH2:36][NH2:37])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[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:37][CH2:36][CH2:35][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[C:4]([C:25]([F:26])([F:28])[F:27])[CH:3]=1

Participants

3

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 69482880HCID 69482880, compound

Product 1

HCID 69482055HCID 69482055, 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 [2-(4-morpholinyl)ethyl]amine employing methods similar to those those described in Example 9 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 a white solid: 1H NMR (d6-DMSO) δ 11.72 (1H, s), 10.34 (1H, br t, J=5 Hz), 8.45 (1H, d, J=1.2 Hz), 7.67 (1H, dd, J=9.3, 2.6 Hz), 7.59-7.50 (4H, m), 7.29 (1H, s), 4.29 (2H, s), 3.56 (4H, m), 3.46 (2H, q, J=6 Hz), 2.40 (4H, m); HRMS calcd for C23H22F4N4O4+H+: 495.1655. Found: 495.1659.

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 a white solid

Sources & evidence

ORD record
ord-0ec1dfcad82c4acf9aa5ca149ea46158
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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