Potassium Carbonate → HCID 66876660, compound

HRID 631667Notes

Reaction equation

HRID 631667 reaction equation
C(O)(=O)C(O)=O.[C:7]([C:11]1[CH:15]=[C:14]([NH2:16])[N:13]([CH2:17][CH3:18])[N:12]=1)([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])[O-].[K+].[K+].C(N(CC)C(C)C)(C)C.Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:36]>ClCCl>[C:7]([C:11]1[CH:15]=[C:14]([NH:16][C:35](=[O:36])[O:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:13]([CH2:17][CH3:18])[N:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 66876716HCID 66876716, compound

Product 1

HCID 66876660HCID 66876660, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3-tert-butyl-1-ethyl-1H-pyrazol-5-amine oxalate (350 mg, 1.36 mmol), potassium carbonate (280 mg, 2 mmol) and N,N-diisopropylethylamine (170 mg, 1.3 mmol) in dichloromethane (3 mL) at rt, was added dropwise, phenyl chloroformate (220 mg, 1.4 mmol) and the reaction mixture was stirred for a further 3 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 phenyl 3-tert-butyl-1-ethyl-1H-pyrazol-5-ylcarbamate (300 mg, 77%) as a colorless solid. LC-MS (ESI) m/z 288 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-02bec0f84b0f4138bbec2ce7507d28cd
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

Loading…