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 1524212노트

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HRID 1524212 반응식
[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

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 127748255-(Chloromethyl)-3-methyl-1,2,4-oxadiazoleHCID 58044589HCID 58044589, 화합물

생성물 1

HCID 565958832-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)-6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
110 °C

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-0e5b875dfd934e85837fd4299bf2be41
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079901B2

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