Hydrochloric Acid → HCID 57422478, compound

HRID 548158Notes

Reaction equation

HRID 548158 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N:13]3[C:17](=[O:18])[N:16](C(OCC)=O)[N:15]([CH3:24])[C:14]3=[O:25])[CH:10]=[N:9]2)=[C:5]([CH3:26])[O:4][N:3]=1.CN(C=O)C.C(#N)C.Cl>CO>[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N:13]3[C:14](=[O:25])[N:15]([CH3:24])[NH:16][C:17]3=[O:18])[CH:10]=[N:9]2)=[C:5]([CH3:26])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21891449acetonitrile N,N-dimethylformamideHCID 57422479HCID 57422479, compound

Product 1

HCID 57422478HCID 57422478, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-2-methyl-3,5-dioxo-1,2,4-triazolidine-1-carboxylate (3.2 g, 8.8 mmol) was stirred in a (1/1) mixture of MeOH/1N aqueous NaOH (100 mL) at ambient temperature for 30 minutes. The mixture was acidified with aqueous 1N HCl (150 mL), extracted with ethyl acetate (3×, 100 mL), dried over sodium sulfate, filtered and concentrated to afford 4-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-methyl-1,2,4-triazolidine-3,5-dione (2.3 g, 89%) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz): δ2.18 (s, 3H), 2.44 (s, 3H), 3.05 (s, 3H), 5.17 (s, 2H), 7.94 (s, 1H), 8.13 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate (3×, 100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f27fd4a4b98b4349ae3da48f8d6eb057
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Reaction notes

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