Hydrochloric Acid → HCID 60207958, compound

HRID 33251Notes

Reaction equation

HRID 33251 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([O:13]CC)=[O:12])[N:8]([CH2:16][C:17](=[O:26])[NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=2)[N:7]=1)=[O:5])[CH3:2].Cl>C1COCC1.O.[OH-].[Na+]>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[N:8]([CH2:16][C:17](=[O:26])[NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 602079571-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-1H-pyrazole-3,5-dicarboxylic acid diethyl ester

Product 1

HCID 60207958HCID 60207958, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 8 g 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-1H-pyrazole-3,5-dicarboxylic acid diethyl ester in 200 ml THF and 50 ml H2O 17.2 ml IN NaOH is added. After standing for 16 h, the solution was acidified using 1 N HCl. THF was removed in vacuo and water was removed by lyophilization. The residue was purified by chromatography on silica gel using ethyl acetate followed by CH2Cl2/MeOH/HOAC/H2O=9/1/0.1/0.1. The fractions containing the product were evaporated and lyophilized to give a white solid. Yield: 4.42 g.

Workup

  1. customTHF was removed in vacuo and water
  2. customwas removed by lyophilization
  3. customThe residue was purified by chromatography on silica gel
  4. additionThe fractions containing the product
  5. customwere evaporated
  6. customto give a white solid

Sources & evidence

ORD record
ord-cf2ee79d763a4cf2a7e527d2f8490d96
Source dataset
uspto-grants-2008_09
Patent number
US07429581B2

Reaction notes

Loading…