Methanol → 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-8-[1-(2-methanesulfonyl-ethyl)-piperidin-4-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Following the procedure for 320, 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-piperidin-4-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt 375 and methyl vinyl sulfone were reacted, with added DCM to aid dissolution. Addition of a mixture of methanol, ethanol and water followed by removal in vacuo of the DCM precipitated the product from the reaction mixture. The resulting solid was collected by filtration to give 476 as an off-white solid (175 mg, 71%). LCMS: RT=3.30 min, [M+H]+=502. 1H NMR δ (ppm) (DMSO-d6): 8.23 (1 H, d, J=8.20 Hz), 8.05 (1 H, s), 7.05 (1 H, dd, J=8.25, 1.78 Hz), 6.89 (1 H, d, J=1.74 Hz), 5.82-5.72 (1 H, m), 4.33-4.27 (2 H, m), 3.37 (2 H, t, J=5.06 Hz), 3.02 (3 H, s), 2.97 (2 H, s), 2.70 (2 H, s), 2.03 (2 H, s), 1.75 (2 H, d, J=12.38 Hz), 1.67-1.55 (2 H, m), 1.50 (6 H, d, J=6.59 Hz). 3 Protons obscurred by solvent peaks

1. dissolutiondissolution
2. customfollowed by removal in vacuo of the DCM
3. customprecipitated the product from the reaction mixture
4. filtrationThe resulting solid was collected by filtration

ORD 기록

ord-7651a9b8f89f4c368bbf03c12ed5f9e4

출처 데이터셋

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08952043B2