Water → HCID 178428575, compound

HRID 1520216Notes

Reaction equation

HRID 1520216 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:18][C:19]4[N:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=4)[S:16][CH:17]=3)[C:10]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:9]2)=CC=1.O>C(O)(C(F)(F)F)=O>[CH3:25][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([NH:18][C:15]2[S:16][CH:17]=[C:13]([C:11]3[C:10]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[N:9][NH:8][CH:12]=3)[N:14]=2)[N:24]=1

Participants

4

Reactant 2

HCID 962WaterHCID 86658567HCID 86658567, compound

Product 1

HCID 178428575HCID 178428575, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 12 Step 2: A solution of 4-(1-(4-methoxybenzyl)-3-phenyl-1H-pyrazol-4-yl)-N-(4-methylpyrimidin-2-yl)thiazol-2-amine (0.17 mmol, 77 mg) in TFA (1 mL) was stirred at 150° C. for 5 minutes under microwave heating. Water was added and was extracted with DCM. The organic layer was dried over MgSO4, was filtered and was concentrated. The crude compound was purified by flash chromatography with silica gel using DCM/AcOEt (100:10 to 50:50) to yield N-(4-methylpyrimidin-2-yl)-4-(3-phenyl-1H-pyrazol-4-yl)thiazol-2-amine (90 μmol, 30 mg, 50%) as a yellow solid.

Workup

  1. temperatureheating
  2. extractionwas extracted with DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationwas filtered
  5. concentrationwas concentrated
  6. customThe crude compound was purified by flash chromatography with silica gel

Sources & evidence

ORD record
ord-911c68b572ed4a47980b3f65f25be8ce
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

Loading…