N-(2-aminoethyl)acetamide → N-[2-(acetylamino)ethyl]-1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide
Reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:21])=[C:5]([C:22](OCC)=[O:23])[C:4]1=[O:27])[CH3:2].[NH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:34])[CH3:33]>>[C:32]([NH:31][CH2:30][CH2:29][NH:28][C:22]([C:5]1[C:4](=[O:27])[N:3]([CH2:1][CH3:2])[C:12]2[C:7]([C:6]=1[OH:21])=[N:8][CH:9]=[C:10]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)[CH:11]=2)=[O:23])(=[O:34])[CH3:33]Participants
3
Procedure
In a similar manner to that described in example 196, from ethyl 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.081 mmol) and N-(2-aminoethyl)acetamide (66 mg, 0.648 mmol) was prepared N-[2-(acetylamino)ethyl]-1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (21 mg, 60% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.31 (br s, 1 H), 8.49 (s, 1 H), 7.38 (s, 1 H), 7.14-7.11 (m, 2 H), 7.01-6.96 (m, 2 H), 6.85 (br s, 1 H), 4.16 (m, 2 H), 4.10 (s, 2 H), 3.54 (m, 2 H), 3.42 (m, 2 H), 1.94 (s, 3 H), 1.20 (m, 3 H); HRMS m/z calcd for C22H24FN4O4: 427.1776 Found: 427.1783.
Sources & evidence
- ORD record
- ord-41897088552d4b408c3a0d03af902516
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691991B2
Reaction notes
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