Potassium Carbonate → HCID 21071282, compound

HRID 1371577Notes

Reaction equation

HRID 1371577 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:23][C:24]1[CH:29]([CH3:30])[CH2:28][CH2:27][CH2:26][C:25]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[K+].[K+]>ClCCl.CC(C)=O.O.CN(C)C=O>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:23][C:24]2[CH:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:26][CH2:27][CH2:28][C:29]=2[CH3:30])=[O:9])[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 115875353-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid2×HCID 21071283HCID 21071283, compound

Product 1

HCID 21071282HCID 21071282, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (i.e. the product of Step F) (1.0 g, 3.11 mmol) in dichloromethane (10 mL) was added dimethylformamide (20 μL) and oxalyl chloride (299 μL, 3.42 mmol). The mixture was stirred at ambient temperature until a clear solution resulted. The solution was then concentrated under reduced pressure and placed under high vacuum (0.1 torr) for 0.5 h. The residue was redissolved in acetone (5 mL) and added to a mixture of ethyl 2-amino-3-methyl-1-cyclohexene-1-carboxylate (i.e. the product of Step B) (570 mg, 3.11 mmol) and potassium carbonate (645 mg, 4.67 mmol) in acetone (10 mL). After stirring ovenight at ambient temperature, water was added and the mixture was filtered through a column of celite and washed with dichloromethane. The eluent was concentrated and purified by silica gel column, chromatography (eluted with 60% then 80% ethyl ether in petroleum ether) to give the title compound as a white foam (0.2 g).

Workup

  1. customresulted
  2. concentrationThe solution was then concentrated under reduced pressure
  3. dissolutionThe residue was redissolved in acetone (5 mL)
  4. stirringAfter stirring ovenight at ambient temperature
  5. filtrationthe mixture was filtered through a column of celite
  6. washwashed with dichloromethane
  7. concentrationThe eluent was concentrated
  8. custompurified by silica gel column, chromatography (
  9. washeluted with 60%

Sources & evidence

ORD record
ord-5b588fdb0ab443d98a6d77ce9e97c7f5
Source dataset
uspto-grants-2007_01
Patent number
US07157475B2

Reaction notes

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