Acetic Acid → HCID 22037242, compound

HRID 1060951Notes

Reaction equation

HRID 1060951 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:11]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.C(O)(=O)C.C(O[C:32]1(O[Si](C)(C)C)[CH2:34][CH2:33]1)C.C([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][N:10]=[C:11]([N:19]3[CH2:20][CH2:21][N:22]([CH:32]4[CH2:34][CH2:33]4)[CH2:23][CH2:24]3)[C:12]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 178478002HCID 178478002, compound

Product 1

HCID 22037242HCID 22037242, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(4-chlorophenyl)-4-(4-pyridyl)-5-(4-piperazinyl)pyrazole (1.95 g; 5.8 mmoles; prepared as set forth in Example A-169) and acetic acid (3.6 g, 60 mmol) containing 5A molecular sieves (6 g) was added [(1-ethoxycyclopropyl)oxy]trimethylsilane (6 g, 35 mmol). After stirring for 5 minutes, sodium cyanoborohydride (1.7 g, 26 mmol) was added and the mixture was refluxed under a nitrogen atmosphere for 6 hours. The reaction mixture was filtered hot and the filtrate concentrated in vacuo. Water (50 mL) was added and the solution made basic with 2N sodium hydroxide. The resultant gel was extracted with dichloroethane and the combined organic extracts dried (MgSO4). Evaporation again yielded a gel which was treated with hot methanol. Upon cooling, the product crystallized to give 1.4 g (63%) of 1-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl)-4-cyclopropylpiperazine, m.p. 264-265° C. Anal. Calc'd. for C21H22ClN5.1.5 H2O: C, 61.99; H, 6.19; N, 17.21. Found: C, 62.05; H, 5.81; N, 16.81.

Workup

  1. customprepared
  2. temperaturethe mixture was refluxed under a nitrogen atmosphere for 6 hours
  3. filtrationThe reaction mixture was filtered hot
  4. concentrationthe filtrate concentrated in vacuo
  5. additionWater (50 mL) was added
  6. extractionThe resultant gel was extracted with dichloroethane
  7. dry with materialthe combined organic extracts dried (MgSO4)
  8. customEvaporation
  9. customagain yielded a gel which
  10. temperatureUpon cooling
  11. customthe product crystallized

Sources & evidence

ORD record
ord-b51834f7f2b847b68379a3da8136d898
Source dataset
uspto-grants-2003_02
Patent number
US06525059B1

Reaction notes

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