Potassium Carbonate → 2-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2368019Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16](=[O:19])[NH:17][N:18]=3)[CH:15]=2)=[CH:6][CH:5]=1.Cl[CH2:23][C:24]1[O:28][N:27]=[C:26]([CH3:29])[N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH3:29][C:26]1[N:25]=[C:24]([CH2:23][N:17]2[C:16](=[O:19])[N:14]3[CH:15]=[C:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:20])[F:21])=[CH:9][CH:8]=4)[CH:11]=[CH:12][C:13]3=[N:18]2)[O:28][N:27]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 90 mg 6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (0.30 mmol), 40 mg 5-(chloromethyl)-3-methyl-1,2,4-oxadiazole (0.30 mmol) and 23 mg potassium carbonate (0.17 mmol) in 2 mL DMA was heated at 110° C. for 2 h. The reaction mixture was then filtered and the filtrate concentrated. The residue was column purified on 12 g silica, eluting with 36 mL 5% ethyl acetate in hexanes, then 5-50% over 60 mL, and then 50% 120 mL. 2-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one was isolated as a yellow solid. m/z (ESI)=392.0 [M+H]+. 1H NMR (δ, d6-DMSO, 400 MHz) 7.95 (dd, 1H) 7.54 (d, 2H), 7.40 (dd, 1H), 7.32 (d, 2H), 7.20 (dd, 1H) 5.43 (s, 2H), 2.40 (s, 3H)

Workup

filtrationThe reaction mixture was then filtered
concentrationthe filtrate concentrated
custompurified on 12 g silica
washeluting with 36 mL 5% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-889d7451b44144fd87a372bf7d210744
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703759B2

Reaction notes

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