Potassium Carbonate → HCID 58081349, compound

HRID 928391Notes

Reaction equation

HRID 928391 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.[NH:11]1[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:19]([O:18][C:16]([C:14]1[CH:15]=[N:11][N:12]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=2)[CH:13]=1)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 5107660[4-(Chloromethyl)phenyl]methanol

Product 1

HCID 58081349HCID 58081349, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (4-Chloromethyl-phenyl)-methanol (600 mg, 3.8 mmol), ethyl 1H-pyrazole-4-carboxylate (537 mg, 3.8 mmol) and potassium carbonate (2.6 g, 19 mmol) in 30 mL acetone was stirred at 50° C. for 3 h. The mixture was filtrated and concentrated in vacuo. The crude was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min) to yield the title compound. LCMS (method A) RtA=1.403 min; [M+H]+=261.0.

Workup

  1. filtrationThe mixture was filtrated
  2. concentrationconcentrated in vacuo
  3. customThe crude was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min)

Sources & evidence

ORD record
ord-259ebb4c272341f89a3a5089ad037b19
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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