2-Morpholinoethylamine → 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364260Notes

Reaction equation

HRID 2364260 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH:19]=3)[C:14]([OH:29])=[C:13]([C:30](OC)=[O:31])[C:12]2=[O:34])=[CH:7][CH:6]=1)=[O:4].[N:36]1([CH2:42][CH2:43][NH2:44])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>CO>[CH3:1][N:2]([CH3:35])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH:19]=3)[C:14]([OH:29])=[C:13]([C:30]([NH:44][CH2:43][CH2:42][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[O:31])[C:12]2=[O:34])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 69480958HCID 69480958, compound

Product 1

HCID 694822061-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner to that described in example 196, from methyl 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.0421 mmol), [2-(4-morpholinyl)ethyl]amine (0.05 mL), and methanol (2 mL), was prepared 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (20 mg, 83% yield) as a tan solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.02 (br s, 1 H), 8.50 (s, 1 H), 7.64 (d, (J=8.4 Hz, 2 H), 7.26 (d, J=8.4 Hz, 2 H), 7.01-6.98 (m, 2 H), 6.94 (m, 2 H), 6.77 (s, 1 H), 3.93 (s, 2 H), 3.71-3.68 (m, 4 H), 3.58 (q, J=12.4, 6.4 Hz, 2 H), 3.15 (s, 3 H), 3.05 (s, 3 H), 2.63 (t, J=6.4 Hz, 2 H), 2.56-2.54 (m, 4 H); MS m/z 574 (M+1).

Sources & evidence

ORD record
ord-93da73f502f94b9b9d21cdf972d0b63d
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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