HCID 86658569, compound → HCID 46836806, compound

HRID 1520218Notes

Reaction equation

HRID 1520218 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[S:16][CH:17]=3)[C:10]([C:25]#[N:26])=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[NH:18][C:15]1[S:16][CH:17]=[C:13]([C:11]2[CH:12]=[N:8][NH:9][C:10]=2[C:25]#[N:26])[N:14]=1

Participants

3

Reactant 1

HCID 86658569HCID 86658569, compound

Product 1

HCID 46836806HCID 46836806, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 13 Step 2: A solution of 1-(4-methoxybenzyl)-4-(2-(pyridin-2-ylamino)thiazol-4-yl)-1H-pyrazole-3-carbonitrile (31 μmol, 12 mg) in TFA (1 mL) was microwaved for 3 minutes at 130° C. After evaporation of the solvent, the crude residue was dissolved in AcOEt. The organic phase was washed with a saturated aqueous solution of Na2CO3, was dried over MgSO4, was filtered and was concentrated. The resulting crude product was purified by flash chromatography over silica gel using DCM/MeOH (100:0 to 95:5) as eluent to yield 4-(2-(pyridin-2-ylamino)thiazol-4-yl)-1H-pyrazole-5-carbonitrile (15 μmol, 4 mg, 48%) as a white solid.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe crude residue was dissolved in AcOEt
  3. washThe organic phase was washed with a saturated aqueous solution of Na2CO3
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated
  7. customThe resulting crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-193fbc7764fb43fbb117cd5b396ad07a
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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