Cesium carbonate → HCID 57422494, compound

HRID 548183Notes

Reaction equation

HRID 548183 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])[CH2:16][NH:15][C:14]3=[O:19])[CH:10]=[N:9]2)=[C:5]([CH3:20])[O:4][N:3]=1.ClC[C:23]1[C:24]([CH3:29])=[N:25][N:26]([CH3:28])[CH:27]=1.[C:30](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:28][N:26]1[C:27]([CH2:30][N:15]2[CH2:16][C:17](=[O:18])[N:13]([C:11]3[CH:10]=[N:9][N:8]([CH2:7][C:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[CH3:20])[CH:12]=3)[C:14]2=[O:19])=[CH:23][C:24]([CH3:29])=[N:25]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 55298635HCID 55298635, compoundHCID 574224243-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione

Product 1

HCID 57422494HCID 57422494, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione (10a) (200 mg, 0.7 mmol), 4-(chloromethyl)-1,3-dimethyl-1H-pyrazole (144 mg, 1 mmol), and cesium carbonate (325 mg, 1 mmol) were dissolved in 2 mL DMF and irradiated in the microwave reactor at 165° C. for 5 minutes. The reaction was cooled to room temperature, and salt precipitate was removed by filtration. The clear solution containing crude product was obtained and was purified by HPLC (10 to 95% Acetonitrile/water; 25 minutes) to afford 1-((1,3-dimethyl-1H-pyrazol-5-yl)methyl)-3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidine-2,4-dione (150 mg, 53%) as a light brown solid. 12.09H NMR (DMSO, 400 MHz): δ (s, 3H), 2.14 (s, 3H), 2.20 (s, 3H), 3.70 (s, 3H), 3.99 (s, 2H), 4.55 (s, 2H), 5.19 (s, 2H), 6.06 (s, H), 7.77 (s, H), 8.17 (s, H). MS M+H calculated for 384.2; found 384.2. Melting point: 145-146° C.

Workup

  1. customirradiated in the microwave reactor at 165° C. for 5 minutes
  2. customsalt precipitate was removed by filtration
  3. additionThe clear solution containing crude product
  4. customwas obtained
  5. customwas purified by HPLC (10 to 95% Acetonitrile/water; 25 minutes)

Sources & evidence

ORD record
ord-0ffcc3f0ee9b4a3c96f48c9833a308b1
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Reaction notes

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