Propyl-2-thiourea → 4-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-propylamino) thiazole
Reaction equation
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[CH2:22]([NH:25][C:26]([NH2:28])=[S:27])[CH2:23][CH3:24]>C(O)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:28]=[C:26]([NH:25][CH2:22][CH2:23][CH3:24])[S:27][C:2]=2[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1Participants
4
Procedure
To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (0.346 g, 0.932 mmol) (Example 26, Step 2) in ethanol (15 mL) in a 25 mL round bottom flask was added N-propylthiourea (0.116 g, 0.979 mmol) with stirring. The resulting solution was heated to reflux for 24 hours. The reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in methylene chloride, washed successively with Na2CO3 (10% solution) and brine, dried over Na2SO4, filtered and reconcentrated in vacuo yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-propylamino) thiazole as a yellow crystalline solid (0.276 g, 76%): mp 181°-182° C. 1H NMR (DMSO-d6) 400 mHz 5 7.97 (t, J=5.37 Hz, 1H), 7.78 (d, J=8.79 Hz, H), 7.42 (dd, J=5.86, 8.79, 2H), 7.37 (d, J=8.79, H), 7.15 (t, J=8.79 Hz, 2H), 3.21 (q, J=6.84, H), 3.18 (s, 3H), 1.60 (m, 2H), 0.91 (t, J=7.33, H). MS (EI): m/z 390 (M+). HRMS Δ=2.4 mmu.