Sodium Carbonate → HCID 178506299, compound

HRID 1910852Notes

Reaction equation

HRID 1910852 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[S:14][CH:15]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[N:17]=3)[C:10]([C:25]([F:28])([F:27])[F:26])=[N:9]2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][C:16]1[N:17]=[C:13]([C:11]2[C:10]([C:25]([F:27])([F:28])[F:26])=[N:9][NH:8][CH:12]=2)[S:14][CH:15]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 67345739HCID 67345739, compound

Product 1

HCID 178506299HCID 178506299, compoundYield 43,636.398%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
140 °C

Procedure

According to Scheme 3 Step 2: A solution of 2-(1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)-N-(pyridin-2-yl)thiazol-4-amine (0.22 mmol, 94 mg) in TFA (1 mL) was stirred under microwave heating at 140° C. during 5 minutes then at 150° C. during 5 minutes. The solution was dropwise poured onto a saturated aqueous solution of Na2CO3 and filtered. The crude compound was purified by flash chromatography over silica gel using DCM/EtOH/NH3 (100:0:0 to 93:6.3:0.7) as eluent to yield N-(pyridin-2-yl)-2-(3-(trifluoromethyl)-1H-pyrazol-4-yl)thiazol-4-amine (96 mmol, 30 mg, 44%) as a slightly orange solid.

Workup

  1. filtrationfiltered
  2. customThe crude compound was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-b2abeb029962464baa071cc1a0f969d5
Source dataset
uspto-grants-2013_12
Patent number
US08604033B2

Reaction notes

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