Sodium Bicarbonate → HCID 18436986, compound

HRID 456536Notes

Reaction equation

HRID 456536 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[S:21][CH:20]=[CH:19][C:16]=3[NH:17][N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22]C(C)([O-])C.[K+].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[S:21][CH:20]=[CH:19][C:16]=3[N:17]([CH3:22])[N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18436985HCID 18436985, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18436986HCID 18436986, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

To a stirred solution of 3-(4-benzyl-piperazin-1-yl)-1H-thieno[3,2-c]pyrazole (318.0 g, 1.07 mol) in THF (2.5 L) was added a mixture of potassium t-butoxide (134.4 g, 1.2 mol) in THF (1.5 L) dropwise over a period of 1 hour while keeping the reaction temperature below 25° C. After complete addition, the mixture was cooled to −30° C. and Mel (65.4 mL, 1.05 mol) was added dropwise over a period of 30 minutes. The mixture is then slowly warmed to room temperature overnight. To the reaction mixture is slowly added saturated NaHCO3 (1 L). The solution is then evaporated to remove the THF and the resulting aqueous mixture is taken up in EtOAc and washed with water and brine. The EtOAc extract is dried (Na2SO4), filtered and evaporated. The viscous concentrate is filtered through a silica gel plug with 1:1 EtOAc/heptane and evaporated yielding a viscous oil that is then dried under vacuum where it solidifies and yields 326.03 g (98%) as a 12:1 ratio of regioisomers in favor of the desired product.

Workup

  1. customthe reaction temperature below 25° C
  2. additionAfter complete addition
  3. additionMel (65.4 mL, 1.05 mol) was added dropwise over a period of 30 minutes
  4. temperatureThe mixture is then slowly warmed to room temperature overnight
  5. customThe solution is then evaporated
  6. customto remove the THF
  7. washwashed with water and brine
  8. extractionThe EtOAc extract
  9. dry with materialis dried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated
  12. concentrationThe viscous concentrate
  13. filtrationis filtered through a silica gel plug with 1:1 EtOAc/heptane
  14. customevaporated
  15. customyielding a viscous oil that
  16. customis then dried under vacuum where it

Sources & evidence

ORD record
ord-8ac432b7f1ba47c69216a6033d78e838
Source dataset
uspto-grants-2007_03
Patent number
US07186724B2

Reaction notes

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