HCID 66889224, compound → HCID 50938617, compound

HRID 1893726Notes

Reaction equation

HRID 1893726 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[S:16][C:17]=3[C:18]#[N:19])[CH:10]=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[NH:8]1[CH:12]=[C:11]([C:13]2[N:14]=[C:15]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[S:16][C:17]=2[C:18]#[N:19])[CH:10]=[N:9]1

Participants

3

Reactant 1

HCID 66889224HCID 66889224, compound

Product 1

HCID 50938617HCID 50938617, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

According to Scheme 7, Step 6: A solution of 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-(pyridin-2-yloxy)thiazole-5-carbonitrile (0.26 mmol, 153 mg) in TFA (5 mL) was stirred at 100° C. for 10 minutes under microwave conditions. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was diluted with EtOAc and was washed with a saturated aqueous solution of NaHCO3. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 4-(1H-pyrazol-4-yl)-2-(pyridin-2-yloxy)thiazole-5-carbonitrile as a white solid (29 mg, 28%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washwas washed with a saturated aqueous solution of NaHCO3
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-c65db581a4ad41009a85f8cc72375977
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

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