Sodium Bicarbonate → HCID 18436986, 화합물

HRID 456536노트

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HRID 456536 반응식
[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

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 184369853-(4-benzyl-piperazin-1-yl)-1H-thieno[3,2-c]pyrazoleHCID 23665647Potassium tert-butoxide

생성물 1

HCID 18436986HCID 18436986, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-30 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ac432b7f1ba47c69216a6033d78e838
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186724B2

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