Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Trifluoromethanesulfonic acid | HCID 62406 | — |
| Reactant | HCID 86658564 | HCID 86658564 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | HCID 46837061 | HCID 46837061 | 5.5% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09073907B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-aca633f3358347bab61bb3fbca152b3f |
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| Source note | uspto-grants-2015_07 |
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