3,5-Dimethylisoxazole-4-isocyanate → HCID 25255370, compound

HRID 507403

Reaction equation

HRID 507403 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:26])[CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]2[CH3:25])=[CH:4][CH:3]=1.[N:27]([C:30]1[C:31]([CH3:36])=[N:32][O:33][C:34]=1[CH3:35])=[C:28]=[O:29]>ClCCl>[CH3:36][C:31]1[C:30]([NH:27][C:28]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:26])[CH2:9][N:10]3[C:14](=[O:15])[C:13]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]3[CH3:25])=[CH:6][CH:7]=2)=[O:29])=[C:34]([CH3:35])[O:33][N:32]=1

Participants

4

Reactant 2

HCID 27362663,5-Dimethylisoxazole-4-isocyanateHCID 68467135HCID 68467135, compound

Product 1

HCID 25255370HCID 25255370, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (+/−)-3-[2-(4-amino-phenyl)-2-oxo-ethyl]-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one (88 mg, 0.25 mmol) and 4-isocyanato-3,5-dimethyl-isoxazole (35 mg, 0.25 mmol) in 3 mL dichloromethane is stirred at room temperature for 18 hours. Subsequently the solvent is evaporated and the residue is dissolved in acetonitrile, the solution filtrated and subjected to preparative HPLC purification (method 3) to yield (+/−)-1-(3,5-dimethyl-isoxazol-4-yl)-3-{4-[2-(2-methyl-5-oxo-4-phenyl-4-propyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-urea (43 mg, 35%), LC/MS at 254 nm; [M+H] 488; Rt 2.648 min.

Workup

  1. customSubsequently the solvent is evaporated
  2. dissolutionthe residue is dissolved in acetonitrile
  3. filtrationthe solution filtrated
  4. customsubjected to preparative HPLC purification (method 3)

Sources & evidence

ORD record
ord-788ec14dbf054e259be1b6dbb050e94f
Source dataset
uspto-grants-2010_08
Patent number
US07786155B2

Linked notes

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