Hydrochloric Acid → HCID 57559703, compound

HRID 1723956Notes

Reaction equation

HRID 1723956 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[CH:16]=[C:15]([C:17](=[O:36])[NH:18][C:19]3[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[C:21]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:20]=3[O:34][CH3:35])[CH:14]=[CH:13][C:12]=2[CH3:37])[CH:10]=1)=[O:5])C.[OH-].[Na+].Cl>CO>[C:25]([C:23]1[CH:22]=[C:21]([NH:29][S:30]([CH3:33])(=[O:31])=[O:32])[C:20]([O:34][CH3:35])=[C:19]([NH:18][C:17]([C:15]2[CH:14]=[CH:13][C:12]([CH3:37])=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)[CH:16]=2)=[O:36])[CH:24]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11685140HCID 11685140, compound

Product 1

HCID 57559703HCID 57559703, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[5-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-pyrazole-4-carboxylic acid ethyl ester (Example 2) (900 mg) was suspended in MeOH (7 mL). A solution of 10% sodium hydroxide (33 mL) was added and the reaction stirred 2 h. The solution was acidified with concentrated HCl to a pH of 4 resulting in a suspension. The suspension was cooled in an ice bath and the solids collected by vacuum filtration. The solids were washed with water, dried under vacuum over P2O5 at 50° C. to provide 1-[5-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-pyrazole-4-carboxylic acid (782 mg, 91%) as a white solid.

Workup

  1. customresulting in a suspension
  2. temperatureThe suspension was cooled in an ice bath
  3. filtrationthe solids collected by vacuum filtration
  4. washThe solids were washed with water
  5. dry with materialdried under vacuum over P2O5 at 50° C.

Sources & evidence

ORD record
ord-8064ad693dd0445aa43d35a5a3d0a21f
Source dataset
uspto-grants-2009_02
Patent number
US07485657B2

Reaction notes

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