Potassium Carbonate → HCID 66876723, compound

HRID 871738Notes

Reaction equation

Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].Cl.[C:18]([C:22]1[CH:26]=[C:25]([NH2:27])[N:24]([CH:28]([CH3:30])[CH3:29])[N:23]=1)([CH3:21])([CH3:20])[CH3:19].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:18]([C:22]1[CH:26]=[C:25]([NH:27][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:24]([CH:28]([CH3:30])[CH3:29])[N:23]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of phenyl chloroformate (170 mg, 1.1 mmol) and potassium carbonate (210 mg, 1.5 mmol) in DCM (3 mL) at 0° C., was added dropwise a solution of 3-tert-butyl-1-isopropyl-1H-pyrazol-5-amine hydrochloride (220 mg, 1 mmol) in N,N-diisopropylethylamine (130 mg, 1 mmol) and the reaction mixture was stirred at 0° C. for 3 h. The mixture was filtrated, concentrated under reduced pressure, and the residue dissolved in dichloromethane. The organic phase was washed water, brine and concentrated under reduced pressure to give the crude product which was purified via recrystallization from diethyl ether to afford phenyl 3-tert-butyl-1-isopropyl-1H-pyrazol-5-ylcarbamate (300 mg, 100%) as a colorless solid. LC-MS (ESI) m/z 302 (M+H)+.

Workup

filtrationThe mixture was filtrated
concentrationconcentrated under reduced pressure
dissolutionthe residue dissolved in dichloromethane
washThe organic phase was washed water, brine
concentrationconcentrated under reduced pressure
customto give the crude product which
customwas purified via recrystallization from diethyl ether

Sources & evidence

ORD record: ord-4d6432526eab41f68e9a9cc680c650e6
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969587B2

Reaction notes

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