Bromopyruvic Acid → 2-{[4-(ethoxycarbonyl)-1H-pyrazol-1-yl]methyl}-1,3-thiazole-4-carboxylic acid

HRID 1257344Notes

Reaction equation

HRID 1257344 reaction equation
[NH2:1][C:2](=[S:14])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]1.Br[CH2:16][C:17](=O)[C:18]([OH:20])=[O:19]>C(#N)C>[CH2:12]([O:11][C:9]([C:7]1[CH:6]=[N:5][N:4]([CH2:3][C:2]2[S:14][CH:16]=[C:17]([C:18]([OH:20])=[O:19])[N:1]=2)[CH:8]=1)=[O:10])[CH3:13]

Participants

4

Reactant 2

HCID 70684Bromopyruvic AcidHCID 58127901Ethyl 1-(carbamothioylmethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 669392482-{[4-(ethoxycarbonyl)-1H-pyrazol-1-yl]methyl}-1,3-thiazole-4-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution (9 mL) of the compound (2.0 g, 9.38 mmol) obtained in Example 1b in acetonitrile was added 3-bromo-2-oxopropanoic acid (1.9 g, 11.3 mmol), and the mixture was stirred at 80° C. for 2 hr. The resulting crystals were collected by filtration and washed with hexane to give the title compound (2.56 g, 97%) as pale-brown crystals.

Workup

  1. filtrationThe resulting crystals were collected by filtration
  2. washwashed with hexane

Sources & evidence

ORD record
ord-4720631a02ab4951b5132373d51a63da
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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