Hydrochloric Acid → HCID 58763940, compound

HRID 859192Notes

Reaction equation

HRID 859192 reaction equation
C([O:3][C:4]([C:6]1[C:10]([NH:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:9]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[N:7]=1)=[O:5])C.[OH-].[K+].Cl>C(O)C.[Na+].[Cl-]>[C:18]([O:17][C:15]([NH:14][CH2:13][CH2:12][NH:11][C:10]1[C:6]([C:4]([OH:5])=[O:3])=[N:7][N:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:9]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58763951HCID 58763951, compound

Product 1

HCID 58763940HCID 58763940, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 5234Sodium ChlorideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(2-tert-butoxycarbonylaminoethylamino)-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (I-4b, 900 mg) in ethanol (50 ml) at room temperature was added 1 N KOH (25 ml). The reaction mixture was heated at 50° C. for 2 hours, cooled to room temperature, diluted with saturated aqueous NaCl, and acidified to pH 3 with 3N HCl. The aqueous solution was extracted with EtOAc (2×) and the combined organic extracts were dried and concentrated in vacuo to give the product I-4c as an amorphous glass (879 mg): +ES MS (M+1) 491.5.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe aqueous solution was extracted with EtOAc (2×)
  3. customthe combined organic extracts were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df8a00322e394165995fef74b665c2a2
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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