Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester → 3-(4-chlorophenyl)-7-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5(4H)-one
Reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[C:5]([NH2:14])[NH:4][N:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[CH2:24][C:25](OCC)=[O:26])=[CH:19][CH:18]=1>N1C=CC=CC=1>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]2[C:2]([CH3:1])=[N:3][N:4]3[C:23]([C:20]4[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=4)=[CH:24][C:25](=[O:26])[NH:14][C:5]=23)=[CH:12][CH:11]=1Participants
Procedure
3-Methyl-4-(4-chlorophenyl)-1H-pyrazol-5-amine (166 mg) and ethyl 3-(4-methoxyphenyl)-3-oxopropanoate (266 mg) are stirred overnight at 95° C. in a pyridine (10 mL) solvent. After lowering reaction temperature 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 141 mg of the target compound is obtained by column chromatography. 1H NMR (CDCl3, 300 MHz) δ 11.40 (br, 1H), 7.98 (d, J=8.7 Hz, 2H), 7.44 (m, 4H), 6.97 (d, J=8.7 Hz, 2H), 4.06 (br, 1H), 3.89 (s, 3H), 2.17 (s, 3H), 2.25 (s, 1H).
Workup
- customreaction temperature to room temperature
- customthe reaction solvent is removed by distillation under reduced pressure
- extractionThe remainder is extracted with ethyl acetate and water
- washThe extracted organic layer is washed with brine
- distillationThe dehydrated organic layer is distilled under reduced pressure
Sources & evidence
- ORD record
- ord-fb9fbfd6898c42e0a63cca40066dbcbd
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975264B2
Reaction notes
Loading…