Lawesson's reagent → 2-Methyl-N-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)thiazol-5-amine
Reaction equation
[C:1]([NH:4][CH2:5][C:6]([NH:8][C:9]1[N:27]=[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=3)[N:11]2[N:10]=1)=O)(=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>>[CH3:2][C:1]1[S:37][C:6]([NH:8][C:9]2[N:27]=[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:18]=4)[N:11]3[N:10]=2)=[CH:5][N:4]=1Participants
3
Procedure
A solution of 2-acetamido-N-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide (46 mg, 0.12 mmol, 1 equiv) and Lawesson's reagent (190 mg, 0.48 mmol, 4.0 equiv) was heated under reflux for 6 hr. The reaction mixture was concentrated in vacuo, and the resulting residue was diluted with water and ethyl acetate. The product was collected by filtration and purified by preparative HPLC to afford product (20 mg, 40% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.41 (s, 1H), 8.71 (t, J=1.6 Hz, 1H), 8.35 (s, 1H), 8.11 (s, 1H), 7.90 (d, J=7.9 Hz, 1H), 7.71 (d, J=7.2 Hz, 1H), 7.60 (m, 1H), 7.37 (dd, J=7.2, 1.3 Hz, 1H), 7.28 (s, 1H), 3.33 (s, 3H), 2.52 (s, 3H).