Hydrochloric Acid → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid 3-methyl ester

HRID 33243Notes

Reaction equation

HRID 33243 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]([O:12]C)=[O:11])[N:7]([CH2:14][C:15]2[CH:19]=[C:18]([C:20]3[S:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[O:17][N:16]=2)[N:6]=1)=[O:4].[OH-].[Na+].Cl>O.C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[N:7]([CH2:14][C:15]2[CH:19]=[C:18]([C:20]3[S:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[O:17][N:16]=2)[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 602079511-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester

Product 1

HCID 602079521-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid 3-methyl ester

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 1.7 g 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester in 10 ml water/THF 1:1, 4 ml of a 1M aqueous NaOH were added at RT and the mixture was stirred for 3 h with LCMS reaction control. Then the reaction mixture was acidified to pH 3 with half concentrated HCl and extracted with DCM (3×50 ml). The organic phase was dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue was subjected to the next reaction step without further purification.

Workup

  1. extractionextracted with DCM (3×50 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was subjected to the next reaction step without further purification

Sources & evidence

ORD record
ord-93dc486557fc4a2698f57b8cd55ecc08
Source dataset
uspto-grants-2008_09
Patent number
US07429581B2

Reaction notes

Loading…