OC(C(F)(F)F)=O.[CH:8]([N:11]1[C:15]([C:16]2[S:17][C:18]3[CH2:19][CH2:20][O:21][C:22]4[CH:29]=[C:28]([CH:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)[CH:27]=[CH:26][C:23]=4[C:24]=3[N:25]=2)=[N:14][CH:13]=[N:12]1)([CH3:10])[CH3:9].[CH:36]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH2:37].C(Cl)Cl.CO>O.C(O)C>[CH:8]([N:11]1[C:15]([C:16]2[S:17][C:18]3[CH2:19][CH2:20][O:21][C:22]4[CH:29]=[C:28]([CH:30]5[CH2:35][CH2:34][N:33]([CH2:37][CH2:36][S:38]([CH3:41])(=[O:40])=[O:39])[CH2:32][CH2:31]5)[CH:27]=[CH:26][C:23]=4[C:24]=3[N:25]=2)=[N:14][CH:13]=[N:12]1)([CH3:10])[CH3:9]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 (1H, d, J=8.20 Hz), 8.05 (1H, s), 7.05 (1H, dd, J=8.25, 1.78 Hz), 6.89 (1H, d, J=1.74 Hz), 5.82-5.72 (1H, m), 4.33-4.27 (2H, m), 3.37 (2H, t, J=5.06 Hz), 3.02 (3H, s), 2.97 (2H, s), 2.70 (2H, s), 2.03 (2H, s), 1.75 (2H, d, J=12.38 Hz), 1.67-1.55 (2H, m), 1.50 (6H, d, J=6.59 Hz). 3 Protons obscured by solvent peaks
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