5-Bromo-2-(4-methylpiperazin-1-yl)pyridine → [8-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-amine

HRID 472364Notes

Reaction equation

HRID 472364 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:21]=[C:22]([NH2:24])[N:23]=3)[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:26]1[CH:27]=[CH:28][C:29]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)=[N:30][CH:31]=1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:21]=[C:22]([NH:24][C:26]4[CH:31]=[N:30][C:29]([N:32]5[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]5)=[CH:28][CH:27]=4)[N:23]=3)[CH:14]=[C:15]([C:17]([F:19])([F:20])[F:18])[CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 164142065-Bromo-2-(4-methylpiperazin-1-yl)pyridineHCID 674814178-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 59612526[8-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-amine

Procedure

[8-(4-Methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-amine was prepared from 8-(4-methanesulfonyl-phenyl)-6-trifluoromethyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine and 1-(5-bromo-pyridin-2-yl)-4-methyl-piperazine in a manner analogous to Step 2d and was isolated as a yellow solid (16% yield). MP 210-215° C. 1H NMR (400 MHz, (CDCl3, δ, ppm): 8.79 (s, 1H), 8.38 (s, 1H), 8.25 (d, J=8.5 Hz, 2H), 8.14 (d, J=7.3 Hz, 2H), 7.90 (d, 1H), 7.80 (s, 1H), 7.49 (d, J=8.2 Hz, 2H), 6.99 (d, J=8.2 Hz, 2H), 6.96 (d, 1H), 6.88 (s, 1H), 3.21 (bm, 4H), 3.13 (s, 3H), 2.66 (bm, 4H), 1.57 (s, 3H). MS=532.1 (MH)+.

Sources & evidence

ORD record
ord-53b47fcc720746619067975aaf239870
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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