Hydrochloric Acid → 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-amine hydrochloride

HRID 548005

Reaction equation

HRID 548005 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([NH:13]C(=O)OC(C)(C)C)[CH:10]=[N:9]2)=[C:5]([CH3:21])[O:4][N:3]=1.[ClH:22]>O1CCOCC1>[ClH:22].[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([NH2:13])[CH:10]=[N:9]2)=[C:5]([CH3:21])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57945015Tert-butyl 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-ylcarbamate

Product 1

HCID 574222641-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-amine hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-ylcarbamate (Example 4-1b) (592 mg, 2 mmol) was stirred in a solution of 4N HCl in dioxane (20 mL) at ambient temperature for 2 hours. The solvent was removed under reduced pressure and the residue was taken up in a 1/1 mixture of ethyl acetate/hexanes (30 mL) and concentrated (twice). The solid was triturated with hexanes and collected by filtration providing 1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-amine hydrochloride (500 mg, 99%) as a white solid. 1H NMR (DMSO-d6, 400 MHz): 2.11 (s, 3H), 2.38 (s, 3H), 5.16 (s, 2H), 7.51 (s, 1H), 8.03 (s, 1H), 10.27 (bs, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was taken up in a 1/1 mixture of ethyl acetate/hexanes (30 mL)
  3. concentrationconcentrated (twice)
  4. customThe solid was triturated with hexanes
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-15c5b37b2f98459c89858421e732f69a
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Linked notes

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