2-Aminoquinoxaline → 6-(8-(Quinoxalin-2-ylamino)pyrido[2,3-b]pyrazin-3-yl)-5-(trifluoromethyl)nicotinamide

HRID 545095Notes

Reaction equation

HRID 545095 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][C:8]([C:12]3[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)=[CH:9][N:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:25][C:26]1[CH:35]=[N:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1>>[N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:34]=[CH:35][C:26]=1[NH:25][C:2]1[C:11]2[C:6](=[N:7][C:8]([C:12]3[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)=[CH:9][N:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2245732-AminoquinoxalineHCID 671914016-(8-Chloropyrido[2,3-b]pyrazin-3-yl)-5-(trifluoromethyl)nicotinamide

Product 1

HCID 586456906-(8-(Quinoxalin-2-ylamino)pyrido[2,3-b]pyrazin-3-yl)-5-(trifluoromethyl)nicotinamide

Procedure

Heat a mixture of 6-(8-chloropyrido[2,3-b]pyrazin-3-yl)-5-(trifluoromethyl)nicotinamide (70.6 mg, 0.2 mmol) and 2-aminoquinoxaline (85.8 mg, 0.6 mmol) in a screw cap vial at 140° C. for 20 hours under N2 atmosphere. Purify the reaction mixture by column chromatography using 1-2% MeOH/EtOAc as eluent to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 11.017 (s, 1H), 9.461 (s, 2H), 9.335 (d, 1H, J=1.1 Hz), 9.307 (s, 1H), 9.129 (d, 1H, J=1.3 Hz), 8.836 (s, 1H), 8.557(s, 1H), 7.975 (m, 3H), 7.789 (t, 1H), 7.647(t, 1H). MS=463.12 (M+H). The IC50 determined as described in Example 6 is less than 1 micromolar.

Workup

  1. temperatureHeat
  2. customcap vial at 140° C. for 20 hours under N2 atmosphere
  3. customPurify the reaction mixture by column chromatography

Sources & evidence

ORD record
ord-ab0376c2c2e84ba0817537d8128587ed
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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