Aniline → 9-Cyano-5-phenylcarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]([OH:21])=O)[N:7]3[C:8](=[O:14])[C:9](=[O:13])[NH:10][C:11]([CH:12]=1)=[C:6]23)#[N:2].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:1]([C:3]1[CH:4]=[C:5]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19](=[O:21])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:7]3[C:8](=[O:14])[C:9](=[O:13])[NH:10][C:11]([CH:12]=1)=[C:6]23)#[N:2]Participants
3
Procedure
A procedure similar to that described in Example 5 was carried out with 9-cyano-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (70 mg, 0.245 mmol) and aniline (70 mg, 0.75 mmol) to give 60 mg of the title compound (68%): mp 171°~176° C. (dec); 1H NMR (270 MHz, DMSO-d6)δ12.22 (bs, 1H), 10.02 (s, 1H), 7.56 (d, 2H, J=7.8 Hz), 7.52 (s, 1H), 7.33 (s, 1H), 7.30 (t, 2H, J=7.8 Hz), 7.05 (t, 1H, J=7.8 Hz), 5.18~5.29 (m, 1H), 3.08 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.87 (dm, 1H, J=17.1 Hz), 2.54~2.70 (m, 2H), 2.12 (dm, 1H, J=13.5 Hz), 1.80~1.97 (m, 1H).
Sources & evidence
- ORD record
- ord-1c2fbcd65ba04440bc7d23d121070122
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616586
Reaction notes
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