Hydrochloric Acid → 2-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-5-[2-(2-methoxy-ethoxy)-ethoxy]-2H-pyrazole-3-carboxylic acid

HRID 33272Notes

Reaction equation

HRID 33272 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:19][C:20](=[O:29])[NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=2)[N:8]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[CH:10]=1)=[O:5])C.[OH-].[K+].Cl>C1COCC1>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:20]([CH2:19][N:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:10][C:9]([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])=[N:8]2)=[O:29])=[N:23][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 602079672-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-5-[2-(2-methoxy-ethoxy)-ethoxy]-2H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 574744152-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-5-[2-(2-methoxy-ethoxy)-ethoxy]-2H-pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.2 g 2-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-5-[2-(2-methoxy-ethoxy)-ethoxy]-2H-pyrazole-3-carboxylic acid ethyl ester in 5 ml THF 10 ml of a aqueous KOH solution (10%) were added and the reaction mixture was stirred for 4 h at RT. Then the mixture was acidified with half concentrated hydrochloric acid to pH 3 and the precipitate collected by filtration and washed with 10 ml of water The product was obtained as a white solid which was dried under reduced pressure.

Workup

  1. filtrationthe precipitate collected by filtration
  2. washwashed with 10 ml of water The product
  3. customwas obtained as a white solid which
  4. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-7c8f16473c34460f829a09c00daec6dc
Source dataset
uspto-grants-2008_09
Patent number
US07429581B2

Reaction notes

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