HCID 67855017, compound → HCID 67855003, compound

HRID 1614501Notes

Reaction equation

HRID 1614501 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:21]2[C:26]([Cl:27])=[CH:25][C:24]([C:28]([F:31])([F:30])[F:29])=[CH:23][N:22]=2)[C:7]=1[CH:8]=[CH:9][C:10]([O:12][C:13]([C:16]([O:18]CC)=[O:17])(C)C)=[O:11])#[N:2]>FC(F)(F)C(O)=O>[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:21]2[C:26]([Cl:27])=[CH:25][C:24]([C:28]([F:29])([F:31])[F:30])=[CH:23][N:22]=2)[C:7]=1[CH:8]=[CH:9][C:10]([O:12][CH2:13][C:16]([OH:18])=[O:17])=[O:11])#[N:2]

Participants

3

Reactant 1

HCID 67855017HCID 67855017, compound

Product 1

HCID 67855003HCID 67855003, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.33 gram (0.0007 mole) of 1,1-dimethylethoxycarbonylmethyl 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylate in 1.3 mL of trifluoroacetic acid was stirred at ambient temperature for one hour. After this time, the reaction mixture was concentrated under reduced pressure at a temperature of about 30° to 50° C. The resultant residue was taken up in toluene, and the concentration procedure was repeated. The residue was shaken with diethyl ether and water and then concentrated under reduced pressure at a temperature of about 45° C., yielding 0.29 gram of 90% pure carboxymethyl 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure at a temperature of about 30° to 50° C
  2. concentrationthe concentration procedure
  3. concentrationconcentrated under reduced pressure at a temperature of about 45° C.

Sources & evidence

ORD record
ord-4b2ba6c448494f38a0ea1ac2a1a01d3a
Source dataset
uspto-grants-1993_03
Patent number
US05198014

Reaction notes

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