CEP 33779 synthesis
- Product Name:CEP 33779
- CAS Number:1257704-57-6
- Molecular formula:C24H26N6O2S
- Molecular Weight:462.57
747413-17-8
![[1,2,4]Triazolo[1,5-a]pyridin-2-amine, 8-[4-(methylsulfonyl)phenyl]-](/CAS/20210305/GIF/1257704-13-4.gif)
1257704-13-4
1257704-57-6
GENERAL STEPS: To an oven-dried reaction tube was added palladium acetate (10 mg), 2,2'-bis(dicyclohexylphosphino)biphenyl (30 mg), 8-[4-(methylsulfonyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine (75 mg), 1-(3-bromophenyl)-4-methylpiperazine (80 mg), cesium carbonate (270 mg) and 1 ,4-dioxane (5 mL). The reaction tube was evacuated and backflushed three times with nitrogen and then sealed. The reaction mixture was heated at 80°C for 72 hours. After completion of the reaction, the mixture was cooled to room temperature. The cooled mixture was diluted with dichloromethane (10 mL), filtered through a diatomaceous earth plug and rinsed with dichloromethane. The filtrate was concentrated by evaporation and purified by column chromatography (using an ISCO automated purification system, an amine-modified silica gel column, and an eluent of 5% to 100% ethyl acetate in hexane solution). The target compound N-[3-(4-methyl-1-piperazinyl)phenyl]-8-[4-(methylsulfonyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine (Compound A) was obtained as a yellow solid (70 mg). Melting point: 232-234 °C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.49 (d, J = 7.2 Hz, 1H), 8.25 (d, J = 7.5 Hz, 2H), 8.08 (d, J = 7.9 Hz, 2H), 7.65 (d, J = 7.7 Hz, 1H), 7.38 (s, 1H), 7.27- 7.20 (m, 1H), 7.04-6.95 (m, 2H), 6.84 (s, 1H), 6.60 (d, J = 8.0 Hz, 1H), 3.30-3.25 (m, 4H), 3.10 (s, 3H), 2.63-2.58 (m, 4H), 2.38 (s, 3H). MS: MS = 463 (MH)+.
747413-17-8
35 suppliers
$171.20/100mg
1257704-13-4
3 suppliers
inquiry
1257704-57-6
94 suppliers
$55.00/500μg
Yield:1257704-57-6 36%
Reaction Conditions:
with dicyclohexyl-({2-[2-(dicyclohexylphosphanyl)phenyl]-phenyl})-phosphane;palladium diacetate;caesium carbonate in 1,4-dioxane at 100; for 72 h;Inert atmosphere;Buchwald-Hartwig coupling;
References:
Dugan, Benjamin J.;Gingrich, Diane E.;Mesaros, Eugen F.;Milkiewicz, Karen L.;Curry, Matthew A.;Zulli, Allison L.;Dobrzanski, Pawel;Serdikoff, Cynthia;Jan, Mahfuza;Angeles, Thelma S.;Albom, Mark S.;Mason, Jennifer L.;Aimone, Lisa D.;Meyer, Sheryl L.;Huang, Zeqi;Wells-Knecht, Kevin J.;Ator, Mark A.;Ruggeri, Bruce A.;Dorsey, Bruce D. [Journal of Medicinal Chemistry,2012,vol. 55,# 11,p. 5243 - 5254] Location in patent:experimental part
![8-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine](/CAS2/GIF/1124382-72-4.gif)
1124382-72-4
100 suppliers
$37.00/250mg
1257704-57-6
94 suppliers
$55.00/500μg
1257704-13-4
3 suppliers
inquiry
1257704-57-6
94 suppliers
$55.00/500μg