Sodium Hydroxide → [3-Methyl-5-phenyl-1-(pyrazin-2-yl)-1H-pyrazol-4-yl]acetic acid

HRID 2068479Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5](=[O:25])[CH2:6][C:7]1[C:8]([CH3:24])=[N:9][N:10]([C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CO>[CH3:24][C:8]1[C:7]([CH2:6][C:5]([OH:25])=[O:4])=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]([C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)[N:9]=1

Participants

Conditions

Temperature: 20 °C

Procedure

0.073 g (1.819 mmol) of 2-molar aqueous sodium hydroxide solution was added to 0.165 g (0.455 mmol) of methyl[3-methyl-5-phenyl-1-(pyrazin-2-yl)-1H-pyrazol-4-yl]acetate (see A3) dissolved in 5 ml of methanol, and the mixture was stirred at 20° C. for 1 h. The methanol was removed under reduced pressure and the residue was poured into a mixture of 10 ml of water and 15 ml of dichloromethane. The aqueous phase was extracted with 15 ml of dichloromethane, acidified with concentrated hydrochloric acid (pH=3) and extracted three times with in each case 15 ml of dichloromethane. Drying of the combined organic phases and removal of the solvent under reduced pressure gave 0.080 g (59.7% of theory) of a colorless foamy solid, melting point 125° C.

Workup

customThe methanol was removed under reduced pressure
additionthe residue was poured into a mixture of 10 ml of water and 15 ml of dichloromethane
extractionThe aqueous phase was extracted with 15 ml of dichloromethane
extractionextracted three times with in each case 15 ml of dichloromethane
customDrying of the combined organic phases and removal of the solvent under reduced pressure
customgave 0.080 g (59.7% of theory) of a colorless foamy solid, melting point 125° C.

Sources & evidence

ORD record: ord-646855cf86da4a5ab47b45b0068ad7c5
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08298994B2

Reaction notes

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