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

HRID 2364258Notes

Reaction equation

HRID 2364258 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].[NH2:36][CH2:37][CH2:38][NH:39][C:40](=[O:42])[CH3:41]>CO>[C:40]([NH:39][CH2:38][CH2:37][NH:36][C:30]([C:13]1[C:12](=[O:34])[N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([N:2]([CH3:35])[CH3:1])=[O:4])=[CH:6][CH:7]=2)[C:20]2[C:15]([C:14]=1[OH:29])=[N:16][CH:17]=[C:18]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[CH:19]=2)=[O:31])(=[O:42])[CH3:41]

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 69480958HCID 69480958, compound

Product 1

HCID 69480184N-[2-(acetylamino)ethyl]-1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner to that described in example 196, from from methyl 1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (8 mg, 0.0168 mmol), N-(2-aminoethyl)acetamide (10 mg, 0.098 mmol) and methanol (2 mL), was prepared N-[2-(acetylamino)ethyl]-1-{4-[(dimethylamino)carbonyl]phenyl}-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (4.9 mg, 54% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.14 (m, 1 H), 8.52 (s, 1 H), 7.65 (d, J=8.4 Hz, 2 H), 7.27 (d, J=8.4 Hz, 2 H), 7.02-6.98 (m, 2 H), 6.95-6.90 (m, 2 H), 6.79 (s, 1 H), 6.03 (br s, 1 H), 3.94 (s, 2 H), 3.57-3.54 (m, 2 H), 3.47-3.42 (m, 2 H), 3.16 (s, 3 H), 3.04 (s, 3 H), 1.95 (s, 3 H); MS m/z 546 (M+1).

Sources & evidence

ORD record
ord-47cbb934c8654df985ab830c776f9ece
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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