Tetrahydrofuran → HCID 117949317, compound

HRID 1474433Notes

Reaction equation

HRID 1474433 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:19])=[O:8])[N:4]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[N:3]=1.C1COCC1.[O-]S(S([O-])=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>O.CO>[NH2:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:19])[C:10]=1[NH:9][C:7]([C:5]1[N:4]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[N:3]=[C:2]([Br:1])[CH:6]=1)=[O:8]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 76315512HCID 76315512, compound

Product 1

HCID 117949317HCID 117949317, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-Bromo-1-(3-chloropyridin-2-yl)-N-(2-methyl-6-nitrophenyl)-1H-pyrazole-5-carboxamide prepared in Step 1 (1.27 g, 2.91 mmol), THF (0.2 M, 14.6 mL) and Na2S2O4 (5.37 g, 26.2 mmol, 9.0 eq) were added to a 100 mL round flask and stirred. In a separate flask, NaHCO3 (2.20 g, 26.2 mmol, 9.0 eq) was dissolved in H2O (0.1 M, 29.1 mL) and slowly added to the reaction solution. MeOH (0.6 M, 4.9 mL) was added to the reaction solution, subjected to a reaction at room temperature for 5 minutes, and the solvent was removed therefrom under reduced pressure upon completion of the reaction. The residue was extracted with ethyl acetate (20 mL x 2) and brine (20 mL x 2), and the organic layer thus obtained was dried over MgSO4 and concentrated under reduced pressure. Upon completion of removing the solvent, the residue was dissolved in a small quantity of ethyl acetate, wetted with ethyl acetate/hexane (1:1) and then filtered. The solvent was removed under reduced pressure to obtain the title compound.

Workup

  1. additionslowly added to the reaction solution
  2. customsubjected to a reaction at room temperature for 5 minutes
  3. customthe solvent was removed
  4. customunder reduced pressure upon completion of the reaction
  5. extractionThe residue was extracted with ethyl acetate (20 mL x 2) and brine (20 mL x 2)
  6. customthe organic layer thus obtained
  7. dry with materialwas dried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customUpon completion of removing the solvent
  10. dissolutionthe residue was dissolved in a small quantity of ethyl acetate
  11. filtrationfiltered
  12. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f7888a579a3549a39c6e3766511b7e13
Source dataset
uspto-grants-2015_04
Patent number
US09018233B2

Reaction notes

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