Water → Methyl [(3-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-pyrazol-5-yl)oxy]acetate

HRID 535012Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:23]=[C:22]([OH:24])[N:21]([CH3:25])[N:20]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:27][C:28]([O:30][CH3:31])=[O:29].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([C:19]2[CH:23]=[C:22]([O:24][CH2:27][C:28]([O:30][CH3:31])=[O:29])[N:21]([CH3:25])[N:20]=2)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 3-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1-methyl-1H-pyrazol-5-ol (0.65 g), methyl bromoacetate (0.38 g, 2.48 mmol), potassium carbonate (0.60 g, 4.3 mmol) in N,N-dimethylformamide (5 mL) was stirred at 40° C. for 4 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to purify the residue by silica gel column chromatography (hexane/ethyl acetate 80:20 to 20:80). Solvent was removed to obtain a solid (0.573 g, 73%). LC/MS; ESI(+) m/z: 415 (M+H)+.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customto purify the residue by silica gel column chromatography (hexane/ethyl acetate 80:20 to 20:80)
customSolvent was removed

Sources & evidence

ORD record: ord-63c82a37fe5b47cd98d7bacb9b9eebb5
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853215B2

Reaction notes

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