4-(Trifluoromethyl)aniline → HCID 44285444, compound

HRID 52528Notes

Reaction equation

HRID 52528 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](O)=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[F:21][C:22]([F:31])([F:30])[C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:27][C:26]3[CH:28]=[CH:29][C:23]([C:22]([F:21])([F:30])[F:31])=[CH:24][CH:25]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

3

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 44285444HCID 44285444, compoundYield 73%

Procedure

A procedure similar to that described in Example 52 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (170 mg, 0.5 mmol) and p-trifluoromethylaniline (83 mg, 0.51 mmol) to give 175 mg of the title compound (73%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.07 (s, 1H), 10.38 (s, 1H), 7.77 (d, 2H, J=8.6 Hz), 7.74 (d, 2H, J=8.6 Hz), 7.24 (bs, 1H), 7.17 (bs, 1H), 5.18~5.27 (m, 1H), 3.06 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.85 (dm, 1H, J=17.1 Hz), 2.65 (d, 2H, J=7.6 Hz), 2.11 (dm, 1H, J=13.5 Hz), 1.82~1.96 (m, 1H).

Sources & evidence

ORD record
ord-d41091f8e0824d9881193e918bbabb6f
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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