Acetic Acid → HCID 178516068, compound

HRID 2401140Notes

Reaction equation

HRID 2401140 reaction equation
[C:1]1([C:7]2[C:8]([C:13]([F:16])([F:15])[F:14])=[N:9][NH:10][C:11]=2[NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:17][CH2:18][C:19](=O)[CH2:20][C:21](OCC)=[O:22].C(O)(=O)C>O>[Cl:17][CH2:18][C:19]1[NH:12][C:11]2[N:10]([N:9]=[C:8]([C:13]([F:15])([F:16])[F:14])[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:21](=[O:22])[CH:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 69484Ethyl 4-chloroacetoacetateHCID 178509120HCID 178509120, compound

Product 1

HCID 178516068HCID 178516068, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Referring to the process as shown in FIG. 2 of the drawings, provide and place 0.227 g of the intermediate 4-phenyl-3-trifluoromethyl-5-amino-1H-pyrazole (1 mmol), 0.130 g of ethyl 4-chloro-3-oxobutanoate and 3 ml of acetic acid (anhydrous acetic acid) into a parallel synthesis instrument (Buchi, Switzerland), allow reflux reaction for 4 hours, stop heating, filling cold water into the low temperature module of the synthesis instrument for precipitation of solid substance, wash with acetic acid, then wash with water until the solid substance is neutral, obtain 30 mg of 5-chloromethyl-3-phenyl-2-trifluoromethylpyrazolo[1,5-a]pyrimidin-7(4H)-one, which is a white solid. The purity is greater than 98% (HPLC-UV by area normalization); ESI-Ms(m/z): 328 (M+1)+; 1HNMR (500 MHz, CD3OD): 7.56 (d, 2H), 7.42 (m, 2H), 7.33 (m, 1H), 6.12 (s, 1H), 4.57 (s, 2H).

Workup

  1. customprovide
  2. temperatureallow reflux
  3. customreaction for 4 hours
  4. temperaturestop heating
  5. customfor precipitation of solid substance
  6. washwash with acetic acid
  7. washwash with water until the solid substance

Sources & evidence

ORD record
ord-283c2d21b2194e58b10a362047b32b30
Source dataset
uspto-grants-2014_08
Patent number
US08796285B2

Reaction notes

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