Hydrochloric Acid → 3-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(3-hydroxybenzyl)-imidazolidine-2,4-dione

HRID 658679Notes

Reaction equation

HRID 658679 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([CH:33]=[CH:34][CH:35]=1)[CH2:12][N:13]1[CH2:17][C:16](=[O:18])[N:15]([C:19]2[CH:20]=[N:21][N:22]([CH2:24][C:25]3[C:26]([CH3:31])=[N:27][O:28][C:29]=3[CH3:30])[CH:23]=2)[C:14]1=[O:32])(C(C)(C)C)(C)C.Cl>CO>[CH3:31][C:26]1[C:25]([CH2:24][N:22]2[CH:23]=[C:19]([N:15]3[C:16](=[O:18])[CH2:17][N:13]([CH2:12][C:11]4[CH:33]=[CH:34][CH:35]=[C:9]([OH:8])[CH:10]=4)[C:14]3=[O:32])[CH:20]=[N:21]2)=[C:29]([CH3:30])[O:28][N:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59524366HCID 59524366, compound

Product 1

HCID 574224313-(1-((3,5-Dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(3-hydroxybenzyl)-imidazolidine-2,4-dioneYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(3-(tert-butyldimethylsilyloxy)benzyl)-3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione (Example 10-10b) (6.00 g, 12.11 mmol) was dissolved in methanol (100 mL) and treated with HCl (2.0 M solution in diethyl ether, 5 equivalents). The solution was refluxed for 2. The mixture was allowed to cool down to room temperature and the solvent was removed. The residue was triturated in toluene, filtered and recrystallized from ethanol at 4° C. to give 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(3-hydroxybenzyl)imidazolidine-2,4-dione (4.50 g, 11.80 mmol, 97%) as a white solid. 1H NMR (DMSO, 400 MHz): 2.15 (s, 3H), 2.39 (s, 3H), 3.97 (s, 2H), 4.43 (s, 2H), 5.18 (s, 2H), 6.68 (m, 3H), 7.12 (m, 1H), 7.80 (s, 1H), 8.17 (s, H), 9.41 (s, H). MS 382 (MH+).

Workup

  1. temperatureThe solution was refluxed for 2
  2. customthe solvent was removed
  3. customThe residue was triturated in toluene
  4. filtrationfiltered
  5. customrecrystallized from ethanol at 4° C.

Sources & evidence

ORD record
ord-fd9b91156a894794835643fab1c204e4
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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