Potassium Carbonate → HCID 67159405, compound

HRID 631684Notes

Reaction equation

HRID 631684 reaction equation
Cl.[C:2]([C:6]1[CH:10]=[C:9]([NH2:11])[N:8]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[N:7]=1)([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26].C(N(CC)C(C)C)(C)C>C1COCC1>[C:2]([C:6]1[CH:10]=[C:9]([NH:11][C:25](=[O:26])[O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:8]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[N:7]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 66876820HCID 66876820, compound

Product 1

HCID 67159405HCID 67159405, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 3-tert-butyl-1-cyclohexyl-1H-pyrazol-5-amine hydrochloride (260 mg, 1 mmol) and potassium carbonate (210 mg, 1.5 mmol) in THF (3 mL) at rt, was added dropwise a solution of phenyl chloroformate (170 mg, 1.1 mmol) in THF (2 mL) and the reaction mixture was stirred for a further 15 h. N,N-Diisopropylethylamine (129 mg, 1 mmol) was added to the reaction mixtureand stirring continued for an additional 4 h. The reaction mixture was filtrated, the filtrate concentrated under reduced pressure and the residue partitioned between dichloromethane and water. The organic layer was separated and washed with brine, then concentrated under reduced pressure to give a solid which was recrystallized from diethyl ether to afford crude phenyl 3-tert-butyl-1-cyclohexyl-1H-pyrazol-5-ylcarbamate (200 mg) which was used without further purification. LC-MS (ESI) m/z 342 (M+H)+.

Workup

  1. stirringstirring
  2. waitcontinued for an additional 4 h
  3. filtrationThe reaction mixture was filtrated
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customthe residue partitioned between dichloromethane and water
  6. customThe organic layer was separated
  7. washwashed with brine
  8. concentrationconcentrated under reduced pressure
  9. customto give a solid which
  10. customwas recrystallized from diethyl ether

Sources & evidence

ORD record
ord-0a4231c6e4294e3285d6801ca6109d06
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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