N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-(piperidin-1-yl)thiazol-2-yl)pyridin-2-amine → 5-(piperidin-1-yl)-4-(1H-pyrazol-4-yl)-N-(pyridin-2-yl)thiazol-2-amine

HRID 1520203Notes

Reaction equation

HRID 1520203 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[S:16][C:17]=3[N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:10]=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[N:18]1([C:17]2[S:16][C:15]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[N:14][C:13]=2[C:11]2[CH:10]=[N:9][NH:8][CH:12]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

3

Reactant 1

HCID 86658557N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-(piperidin-1-yl)thiazol-2-yl)pyridin-2-amine

Product 1

HCID 468366515-(piperidin-1-yl)-4-(1H-pyrazol-4-yl)-N-(pyridin-2-yl)thiazol-2-amineYield 103.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 5 Step 3: A solution N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-(piperidin-1-yl)thiazol-2-yl)pyridin-2-amine (0.58 mmol, 260 mg) in TFA (4 mL) was microwaved for 8 minutes at 140° C. After evaporation of the solvent, the crude residue was neutralized with a solution of NaOH (1 M). The aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield 5-(piperidin-1-yl)-4-(1H-pyrazol-4-yl)-N-(pyridin-2-yl)thiazol-2-amine (0.60 mmol, 195 mg, 99%) as a pale yellow solid.

Workup

  1. customAfter evaporation of the solvent
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationwas filtered
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-11704980f8804d70802bca3350307b03
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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