Hydrochloric Acid → 4-[3-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-ureido]benzoic acid

HRID 499197Notes

Reaction equation

C([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[N:16]([CH3:24])[N:17]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:19]=2)=[O:13])=[CH:7][CH:6]=1)C.[OH-].[Na+].Cl>C(O)C.C(OCC)(=O)C>[C:20]([C:18]1[CH:19]=[C:15]([NH:14][C:12](=[O:13])[NH:11][C:8]2[CH:7]=[CH:6][C:5]([C:4]([OH:25])=[O:3])=[CH:10][CH:9]=2)[N:16]([CH3:24])[N:17]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 4-[3-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-ureido]benzoic acid ethyl ester (0.24 g, 0.71 mmol) in ethanol (4 mL) is added 1 N aq. NaOH solution (2 mL) and the mixture is heated at 80° C. for 2 hours. Then, 1 N HCl is added until pH 6 and the mixture is diluted with ethyl acetate. The organic phase is washed once with aqueous sodium chloride solution and dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 0.19 g (0.59 mmol), 83% as white solid. ES+(m/z) 317 [M+H].

Workup

washThe organic phase is washed once with aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated under reduced pressure
customto give 0.19 g (0.59 mmol), 83% as white solid

Sources & evidence

ORD record: ord-103db95bea444ed98e22c21a965358de
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767674B2

Reaction notes

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