Potassium Carbonate → 5-(1-{[3-(2-Methoxyethoxy)phenyl]methyl}-5-methyl-1H-1,2,4-triazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

HRID 1475229Notes

Reaction equation

HRID 1475229 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][C:8]1[N:12]([CH2:13][C:14]2[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)[N:11]=[C:10]([C:21]2[O:25][N:24]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)[N:22]=2)[N:9]=1.Br[CH2:38][CH2:39][O:40][CH3:41]>CN(C=O)C.O>[CH3:41][O:40][CH2:39][CH2:38][O:20][C:16]1[CH:15]=[C:14]([CH2:13][N:12]2[C:8]([CH3:7])=[N:9][C:10]([C:21]3[O:25][N:24]=[C:23]([C:26]4[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:34])[F:35])=[CH:28][CH:27]=4)[N:22]=3)=[N:11]2)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 86711921HCID 86711921, compound

Product 1

HCID 867119225-(1-{[3-(2-Methoxyethoxy)phenyl]methyl}-5-methyl-1H-1,2,4-triazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of K2CO3 (19.9 mg, 0.144 mmol), 3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)phenol (Example 59; 30.0 mg, 0.072 mmol) and 1-bromo-2-methoxyethane (19.9 mg, 0.144 mmol) in DMF (0.36 mL) was stirred at RT for 16 h. The mixture was diluted with H2O and extracted with 4:1 CHCl3:i-PrOH. The organic layer was separated, dried with MgSO4 and concentrated under reduced pressure. The residue was dissolved in DMSO and purified using Prep-HPLC to furnish the title compound. MS (ES+) C22H20F3N5O4 requires: 475. found 476 [M+H]+; 1H-NMR (600 MHz, CD3OD) δ ppm 8.29 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.1 Hz, 2H), 7.28 (m, 1H), 6.91 (m, 1H), 6.83 (d, J=7.6 Hz, 1H), 6.81 (m, 1H), 5.42 (s, 2H), 4.09 (m, 2H), 3.73 (m, 2H), 3.43 (s, 3H), 2.52 (s, 3H).

Workup

  1. extractionextracted with 4:1 CHCl3
  2. customThe organic layer was separated
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in DMSO
  6. custompurified

Sources & evidence

ORD record
ord-c124563e9fb9454e85a1ae8a613f842c
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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