Trifluoromethanesulfonic acid → HCID 50940353, compound

HRID 1893714Notes

Reaction equation

HRID 1893714 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([O:18][C:19]4[N:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[S:16][CH:17]=3)[C:10]([CH3:25])=[N:9]2)=CC=1.FC(F)(F)S(O)(=O)=O>C(O)(C(F)(F)F)=O>[CH3:25][C:10]1[NH:9][N:8]=[CH:12][C:11]=1[C:13]1[N:14]=[C:15]([O:18][C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[S:16][CH:17]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 66888334HCID 66888334, compound

Product 1

HCID 50940353HCID 50940353, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

According to Scheme 2, Step 6: To a solution of 4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl)-2-(pyrimidin-2-yloxy)thiazole (0.18 mmol, 67 mg) in TFA (1.8 mL) was added trifluoromethanesulfonic acid (1.77 mmol, 156 μl). The reaction mixture was stirred for 8 minutes at 80° C. under microwave conditions. The crude mixture was quenched with water and the aqueous phase was extracted with DCM. The organic layer was dried over MgSO4, was filtered and was evaporated to dryness. The crude residue was purified by preparative TLC using DCM/EtOH/NH3 (100:0:0 to 93:6.7:0.3) as eluent to yield 4-(5-methyl-1H-pyrazol-4-yl)-2-(pyrimidin-2-yloxy)thiazole (12 μmol, 3.2 mg, 7%) as a beige solid.

Workup

  1. customThe crude mixture was quenched with water
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationwas filtered
  5. customwas evaporated to dryness
  6. customThe crude residue was purified by preparative TLC

Sources & evidence

ORD record
ord-13fabbc5ec984dc5b386aa9fbfa289e3
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

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