Hydrochloric Acid → 5-Amino-1-methyl-4-(3-phthalimidopropyl)pyrazole

HRID 349522Notes

Reaction equation

HRID 349522 reaction equation
[CH3:1][N:2]1[C:6]([NH:7]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:5]([CH2:27][CH2:28][CH2:29]O)[CH:4]=[N:3]1.[C:31]1(=[O:41])[NH:35][C:34](=[O:36])[C:33]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:32]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.Cl>O1CCCC1.O1CCOCC1.O>[NH2:7][C:6]1[N:2]([CH3:1])[N:3]=[CH:4][C:5]=1[CH2:27][CH2:28][CH2:29][N:35]1[C:31](=[O:41])[C:32]2=[CH:40][CH:39]=[CH:38][CH:37]=[C:33]2[C:34]1=[O:36]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 17962027HCID 17962027, compound

Product 1

HCID 179620255-Amino-1-methyl-4-(3-phthalimidopropyl)pyrazoleYield 77.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)propanol (4.0 g, 10 mmol), phthalimide (1.5 g, 10 mmol) and triphenylphosphine (4.0 g, 15 mmol) in tetrahydrofuran (20 ml) was added diisopropyl azodicarboxylate (3.0 g, 15 mmol), and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added 4 mol/l hydrogen chloride solution in dioxane (10 ml), and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added water, and the mixture was washed with ethyl acetate. The organic layer was separated, and the aqueous layer was adjusted to pH 9 with 10% aqueous sodium carbonate solution. The solution was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with ethyl acetate and dried in vacuo to give 5-amino-1-methyl-4-(3-phthalimidopropyl)pyrazole (2.2 g) as a solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. washthe mixture was washed with ethyl acetate
  3. customThe organic layer was separated
  4. extractionThe solution was extracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ethyl acetate
  9. customdried in vacuo

Sources & evidence

ORD record
ord-fb98834c1b6a46fdb46a30c9a7f17c24
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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