Sodium Carbonate → HCID 46836994, compound

HRID 1520210Notes

Reaction equation

HRID 1520210 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][C:3]=1[C:14]1[CH:15]=[N:16][N:17](CC2C=CC(OC)=CC=2)[CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][C:3]=1[C:14]1[CH:15]=[N:16][NH:17][CH:18]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 86658562HCID 86658562, compound

Product 1

HCID 46836994HCID 46836994, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
120 °C

Procedure

According to Scheme 7, Step 2: A mixture of 5-chloro-4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-N-(pyrimidin-2-yl)thiazol-2-amine (0.33 mmol, 130 mg) in TFA (1 mL) was stirred for 8 minutes at 120° C. under microwave activation. The reaction mixture 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. The crude compound was purified by flash chromatography with silica gel using DCM/MeOH (96:4) as eluent to afford 5-chloro-4-(1H-pyrazol-4-yl)-N-(pyrimidin-2-yl)thiazol-2-amine (0.26 mmol, 74 mg, 81%) as a beige 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. customThe crude compound was purified by flash chromatography with silica gel

Sources & evidence

ORD record
ord-08a12ab9d960419dab7ba92aa933c58b
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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