2-Morpholinoethylamine → HCID 69480452, compound

HRID 2364238Notes

Reaction equation

HRID 2364238 reaction equation
[NH2:1][C:2](=[O:29])[CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23](OCC)=[O:24])[C:5]1=[O:28].[NH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>>[NH2:1][C:2](=[O:29])[CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[O:24])[C:5]1=[O:28]

Participants

3

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 69482140HCID 69482140, compound

Product 1

HCID 69480452HCID 69480452, compound

Procedure

This compound was prepared from ethyl 1-(2-amino-2-oxoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 4-(2-aminoethyl)morpholine 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 an off-white rigid foam: 1H NMR (CDCl3) δ 10.36 (1H, m), 8.56 (1H, s), 7.61 (1H, s), 7.15 (2H, dd, J=8.5, 5.5 Hz), 7.01 (2H, t, J=8.5 Hz), 6.87 (1H, br s), 5.65 (1H, br s), 4.81 (2H, s), 4.12 (2H, s), 3.98 (4H, m), 3.91 (2H, q, J=6 Hz), 3.75 (2H, m), 3.37 (2H, t, J=6 Hz), 2.92 (2H, br); HRMS calcd for C24H26FN5O5+H+: 484.1996. Found: 484.1987.

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 rigid foam

Sources & evidence

ORD record
ord-85443d85c44241eeac8eab654912a75f
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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