N-(2-aminoethyl)acetamide → HCID 69480435, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:26])=[C:14]([C:21](OCC)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:27][CH2:28][CH2:29][NH:30][C:31](=[O:33])[CH3:32]>>[C:31]([NH:30][CH2:29][CH2:28][NH:27][C:21]([C:14]1[C:15](=[O:20])[N:16]([CH3:19])[C:17]2[C:12]([C:13]=1[OH:26])=[N:11][CH:10]=[C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH:18]=2)=[O:22])(=[O:33])[CH3:32]Participants
3
Procedure
In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.056 mmol) described in example 92 and N-(2-aminoethyl)acetamide (74 mg, 0.730 mmol), was prepared N-[2-(acetylamino)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (9 mg, 39% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.39 (br s, 1 H), 8.56 (s, 1 H), 7.39 (s, 1 H), 7.17-7.15 (m, 2 H), 7.04-6.94 (m, 2 H), 6.09 (br s, 1 H), 4.13 (s, 2 H), 3.61-3.58 (m, 2 H), 3.57 (s, 3 H), 3.51-3.48 (m, 2 H), 1.98 (s, 3 H); MS m/z 413 (M+1).
Sources & evidence
- ORD record
- ord-336edbb368cb46c6b7ef5b26b785bbe3
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691991B2
Reaction notes
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