Sodium Bicarbonate → ethyl 1-[(4-carbamoyl-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

HRID 1257345Notes

Reaction equation

HRID 1257345 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[S:13][CH:14]=[C:15]([C:17]([OH:19])=O)[N:16]=2)[CH:10]=1)=[O:5])[CH3:2].[NH4+].O[N:22]1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:17]([C:15]1[N:16]=[C:12]([CH2:11][N:9]2[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8]2)[S:13][CH:14]=1)(=[O:19])[NH2:22]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 669392482-{[4-(ethoxycarbonyl)-1H-pyrazol-1-yl]methyl}-1,3-thiazole-4-carboxylic acid

Product 1

HCID 58127585ethyl 1-[(4-carbamoyl-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylateYield 52.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (7 mL) of the compound (1.0 g, 3.56 mmol) obtained in Example 33a in N,N-dimethylformamide were added 1-ethyl-3-(3-dimethylaminopropyl)carboditmide hydrochloride (WSC, 820 mg, 4.27 mmol) and 1-hydroxy-1H-benzotriazole ammonium salt (704 mg, 4.63 mmol), and the mixture was stirred at room temperature for 4 hr. After confirmation of the termination of the reaction by TLC, saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-ethyl acetate) and recrystallization (ethyl acetate-hexane) to give the title compound (524 mg, 52%) as colorless crystals.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by column chromatography (hexane-ethyl acetate) and recrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-6322138885034792ac300a0a2f8e219b
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

Loading…