Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate → 2-cyclopropyl3-(4-chlorophenyl)-7-(4-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5(4H)-one

HRID 872120Notes

Reaction equation

HRID 872120 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:14]3[CH2:16][CH2:15]3)=[N:10][NH:11][C:12]=2[NH2:13])=[CH:4][CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[CH2:25][C:26](OCC)=[O:27])=[CH:20][CH:19]=1>N1C=CC=CC=1>[CH:14]1([C:9]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[C:12]3[NH:13][C:26](=[O:27])[CH:25]=[C:24]([C:21]4[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=4)[N:11]3[N:10]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 2758844Ethyl 3-(4-Fluorophenyl)-3-OxopropanoateHCID 178509102HCID 178509102, compound

Product 1

HCID 1363939242-cyclopropyl3-(4-chlorophenyl)-7-(4-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5(4H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(4-Chlorophenyl)-3-cyclopropyl-1H-pyrazol-5-amine (121 mg) and ethyl 3-(4-fluorophenyl)-3-oxopropanoate (0.095 mL) are stirred overnight in a pyridine (7 mL) solvent at 95° C. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The extracted organic layer is washed with brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is distilled under reduced pressure and purified by column chromatography to yield 75 mg of the target compound. 1H NMR (CDCl3, 300 MHz): δ 10.15 (br, 1H), 8.02 (m, 2H), 7.42 (m, 4H), 7.18 (m, 2H), 4.08 (br, 1H), 1.80 (m, 1H) 0.89 (m, 4H).

Workup

  1. customthe reaction solvent is removed by distillation under reduced pressure
  2. extractionThe remainder is extracted with ethyl acetate and water
  3. washThe extracted organic layer is washed with brine
  4. distillationThe dehydrated organic layer is distilled under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-e63d7d4a655f4befac2eb875df4731e3
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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