Acetic Acid → 4-(4-Methyl-6-(4-(trifluoromethyl)pyridin-2-ylamino)-2,3'-bipyridin-6'-ylamino)piperidine-1-carboxamide
Reaction equation
[O-:1][C:2]#[N:3].[K+].C(O)(=O)C.[CH3:9][C:10]1[CH:15]=[C:14]([NH:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=2)[N:13]=[C:12]([C:27]2[CH:28]=[N:29][C:30]([NH:33][CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)=[CH:31][CH:32]=2)[CH:11]=1>C1COCC1>[CH3:9][C:10]1[CH:15]=[C:14]([NH:16][C:17]2[CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=[CH:19][N:18]=2)[N:13]=[C:12]([C:27]2[CH:28]=[N:29][C:30]([NH:33][CH:34]3[CH2:39][CH2:38][N:37]([C:2]([NH2:3])=[O:1])[CH2:36][CH2:35]3)=[CH:31][CH:32]=2)[CH:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Potassium cyanate (9.47 mg, 0.117 mmol), acetic acid (0.017 mL, 0.292 mmol), 4-methyl-N6′-(piperidin-4-yl)-N6-(4-(trifluoromethyl)pyridin-2-yl)-2,3′-bipyridine-6,6′-diamine (25 mg, 0.058 mmol), and THF (1 mL) were combined. The mixture was stirred at room temperature for 16 hours. The crude solution was purified via reverse phase high pressure liquid chromatography to afford 4-(4-methyl-6-(4-(trifluoromethyl)pyridin-2-ylamino)-2,3′-bipyridin-6′-ylamino)piperidine-1-carboxamide. MS ESI calcd. for C23H25F3N7O [M+H]+ 472. found 472. 1H NMR (500 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.53-8.49 (m, 3H), 8.28 (s, 1H), 8.24 (d, J=6.5 Hz, 1H), 7.44 (s, 1H), 7.39 (s, 1H), 7.22-7.16 (m, 2H), 4.42 (m, 1H), 3.80 (m, 1H), 3.72-3.65 (m, 2H), 3.45 (dd, J=11.0, 4.0 Hz, 1H), 2.36 (s, 3H), 2.22 (m, 1H), 2.00 (m, 1H), 1.82 (s, 3H). rhSyk IC50=4 nM.
Workup
- customThe crude solution was purified via reverse phase high pressure liquid chromatography
Sources & evidence
- ORD record
- ord-4bebbe1a4250412e99b2d3a2ee72be3d
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145391B2
Reaction notes
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