Sodium Hydroxide → 2-(1H-pyrazol-4-yl)-N-(pyridin-2-yl)thiazol-4-amine

HRID 1910848Notes

Reaction equation

HRID 1910848 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)[CH:10]=[N:9]2)=CC=1.[OH-].[Na+]>C(O)(C(F)(F)F)=O>[NH:9]1[CH:10]=[C:11]([C:13]2[S:14][CH:15]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:17]=2)[CH:12]=[N:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67344078N-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-4-yl)pyridin-2-amine

Product 1

HCID 532590302-(1H-pyrazol-4-yl)-N-(pyridin-2-yl)thiazol-4-amineYield 61.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 1 Step 10: A solution of N-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-4-yl)pyridin-2-amine (0.39 mmol, 143 mg) in TFA (2 mL) was microwaved for 10 minutes at 120° C. The reaction mixture was neutralized with a solution of NaOH (1 M) and was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated. The resulting crude product was purified by flash chromatography over silica gel using DCM/EtOH/NH3 (100:0:0 to 90:9:1) as eluent to yield 2-(1H-pyrazol-4-yl)-N-(pyridin-2-yl)thiazol-4-amine (0.24 mmol, 58 mg, 61%) as an orange solid.

Workup

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

Sources & evidence

ORD record
ord-44587745a4cf4994a2e4a1936fb4ff94
Source dataset
uspto-grants-2013_12
Patent number
US08604033B2

Reaction notes

Loading…