1-(6-Methylpyridin-2-yl)piperazine → methyl-6-(4-(2-(4-(6-methylpyridin-2-yl)piperazin-1-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]tria-zolo[4,5-c]pyridine-4-carbonitrile

HRID 517995Notes

Reaction equation

CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[C:19]([C:21]#[N:22])[C:18]3[N:23]=[N:24][N:25]([CH3:26])[C:17]=3[CH:16]=2)=[CH:11][C:10]=1[C:27]([F:30])([F:29])[F:28])(=O)=O.[CH3:31][C:32]1[N:37]=[C:36]([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH:35]=[CH:34][CH:33]=1>CN1CCCC1>[CH3:26][N:25]1[C:17]2[CH:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:41]4[CH2:42][CH2:43][N:38]([C:36]5[CH:35]=[CH:34][CH:33]=[C:32]([CH3:31])[N:37]=5)[CH2:39][CH2:40]4)=[C:10]([C:27]([F:28])([F:29])[F:30])[CH:11]=3)[N:20]=[C:19]([C:21]#[N:22])[C:18]=2[N:23]=[N:24]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-(4-(4-cyano-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl methanesulfonate (0.15 g) and 1-(6-methylpyridin-2-yl)piperazine (0.361 g) in N-methylpyrollidine (2 ml) was heated at 150° C. under microwave condition for 30 minutes. Solvent removed under vacuum and residue dissolved in methanol (1 ml) and purified by basic prep HPLC to give methyl-6-(4-(2-(4-(6-methylpyridin-2-yl)piperazin-1-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (0.0132 g). 1H NMR (MeOD) δ: 8.45 (m, 3H), 7.43 (m, 2H), 6.57 (m, 2H), 4.46 (s, 3H), 4.41 (m, 2H), 3.35 (m, 3.35), 2.97 (m, 2H), 2.78 (m, 4H), 2.35 (s, 3H). MS m/z 523.2 (M+H).

Workup

customSolvent removed under vacuum and residue
dissolutiondissolved in methanol (1 ml)
custompurified by basic prep HPLC

Sources & evidence

ORD record: ord-1f1cb4398c2a4f1ab558954efc3ae715
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115126B2

Reaction notes

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