Hydrochloric Acid → HCID 86694310, compound

HRID 69107Notes

Reaction equation

[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9]C(=O)C)=[C:4]([C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:16]=[CH:15][CH:14]=2)[CH:3]=1.Cl.C(=O)([O-])O.[Na+].[OH-].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH2:9])=[C:4]([C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:16]=[CH:15][CH:14]=2)[CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3.96 g of N-{4-bromo-5-methyl-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]phenyl}acetamide and 18 mL of 12 M hydrochloric acid was stirred at 120° C. for 40 minutes. The reaction mixture was cooled to room temperature, then poured into a mixture of a saturated aqueous sodium hydrogen carbonate solution/ethyl acetate, and adjusted to pH 10 with a 6 M aqueous sodium hydroxide solution. The aqueous layer was separated, and then the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 3.36 g of 4-bromo-5-methyl-2-[1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]aniline.

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe aqueous layer was separated
washthe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record: ord-9653670544604896948132dc3b8c958c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822448B2

Reaction notes

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