Water → HCID 68664339, compound

HRID 452596Notes

Reaction equation

HRID 452596 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[O:17][C:16]([SH:18])=[N:15][N:14]=3)=[CH:10][CH:11]=2)[CH:6]=[N:5]1.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[O:17][C:16]([S:18][CH2:24][C:23]4[CH:26]=[CH:27][CH:28]=[C:21]([C:20]([F:19])([F:29])[F:30])[CH:22]=4)=[N:15][N:14]=3)=[CH:10][CH:11]=2)[CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 178496777HCID 178496777, compound

Product 1

HCID 68664339HCID 68664339, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 5-[1-(methoxymethyl)-1H-indazol-5-yl]-1,3,4-oxadiazole-2-thiol (525 mg, 2.00 mmol), 3-(trifluoromethyl)benzyl chloride (0.372 mL, 2.40 mmol), and potassium carbonate (415 mg, 3.00 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 5 hr. The reaction mixture was poured into water, the precipitate was collected by filtration, purified by basic silica gel column chromatography (tetrahydrofuran) and recrystallized from hexane/tetrahydrofuran to give the title compound (821 mg, yield 98%) as colorless crystals.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. custompurified by basic silica gel column chromatography (tetrahydrofuran)
  3. customrecrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-d1006dd097c444c887ac65bb2443c41e
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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