Sodium Carbonate → HCID 46837061, compound

HRID 1520213Notes

Reaction equation

HRID 1520213 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:22][C:23]4[N:28]=[C:27]([CH3:29])[CH:26]=[CH:25][N:24]=4)[S:16][C:17]=3[C:18]([F:21])([F:20])[F:19])[CH:10]=[N:9]2)=CC=1.FC(F)(F)S(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O>[CH3:29][C:27]1[CH:26]=[CH:25][N:24]=[C:23]([NH:22][C:15]2[S:16][C:17]([C:18]([F:21])([F:19])[F:20])=[C:13]([C:11]3[CH:10]=[N:9][NH:8][CH:12]=3)[N:14]=2)[N:28]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 62406Trifluoromethanesulfonic acidHCID 86658564HCID 86658564, compound

Product 1

HCID 46837061HCID 46837061, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 9 Step 4: A solution of 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-N-(4-methylpyrimidin-2-yl)-5-(trifluoromethyl)thiazol-2-amine (0.40 mmol, 180 mg) and trifluoromethanesulfonic acid (4.84 mmol, 430 μL) in TFA (1 mL) was stirred for 8 minutes at 80° C. under microwave activation. The reaction solution was neutralized with a saturated aqueous solution of Na2CO3 and extracted with AcOEt. The combined organic layers were dried over MgSO4, were filtered and were evaporated under reduced pressure to give a brown solid. The resulting crude product was purified by flash chromatography over silica gel using DCM/MeOH (100:0 to 95:5) to yield N-(4-methylpyrimidin-2-yl)-4-(1H-pyrazol-4-yl)-5-(trifluoromethyl)thiazol-2-amine (22 μmol, 7 mg, 5.5%) as a white solid.

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationwere filtered
  4. customwere evaporated under reduced pressure
  5. customto give a brown solid
  6. customThe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-aca633f3358347bab61bb3fbca152b3f
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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