N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine → 5-fluoro-N-(6-methylpyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine

HRID 1520206Notes

Reaction equation

HRID 1520206 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=4)[S:16][C:17]=3[F:18])[CH:10]=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[F:18][C:17]1[S:16][C:15]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=2)=[N:14][C:13]=1[C:11]1[CH:12]=[N:8][NH:9][CH:10]=1

Participants

3

Reactant 1

HCID 86658559N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine

Product 1

HCID 468367265-fluoro-N-(6-methylpyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amineYield 50%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 6 Step 4: A solution of N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine (0.24 mmol, 95 mg) in TFA (3 mL) was microwaved for 8 minutes at 140° C. After evaporation of the solvent, the reaction mixture was neutralized with a solution of NaOH (1 M). The aqueous phase was extracted with DCM and with AcOEt. The organic phase was dried over MgSO4, was filtered and was concentrated. The resulting crude product was washed with Et2O to yield 5-fluoro-N-(6-methylpyridin-2-yl)-4-(1H-pyrazol-4-yl)thiazol-2-amine (0.12 mmol, 33 mg, 50%) as a beige solid.

Workup

  1. customAfter evaporation of the solvent
  2. extractionThe aqueous phase was extracted with DCM and with AcOEt
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationwas filtered
  5. concentrationwas concentrated
  6. washThe resulting crude product was washed with Et2O

Sources & evidence

ORD record
ord-c3592a2b046e4334a3a4958cc275bd32
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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