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

HRID 2364288Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([OH:26])=[C:10]([C:27](OCC)=[O:28])[C:9]2=[O:32])=[CH:4][CH:3]=1.[NH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:39])[CH3:38]>>[C:37]([NH:36][CH2:35][CH2:34][NH:33][C:27]([C:10]1[C:9](=[O:32])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:17]2[C:12]([C:11]=1[OH:26])=[N:13][CH:14]=[C:15]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[CH:16]=2)=[O:28])(=[O:39])[CH3:38]

Participants

Reactant 2

HCID 66082N-(2-aminoethyl)acetamide

HCID 59799019Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69480968N-[2-(acetylamino)ethyl]-1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 57%

Procedure

In a similar manner to that described in example 196, from ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.043 mmol) and N-(2-aminoethyl)acetamide (60 mg, 0.595 mmol), was prepared N-[2-(acetylamino)ethyl]-1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (12 mg, 57% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.17 (br s, 1 H), 8.54 (s, 1 H), 7.32-7.27 (m, 2 H), 7.22-7.18 (m, 2 H), 7.03-6.93 (m, 4 H), 6.74 (s, 1 H), 6.03 (br s, 1 H), 3.96 (s, 2 H), 3.58 (m, 2 H), 3.46 (m, 2 H), 1.97 (s, 3 H); MS m/z 493 (M+1).

Sources & evidence

ORD record: ord-8f0c7c1deb6747e1888331392ffb5ee3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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