Dimethyl Sulfoxide → HCID 178438503, compound

HRID 2048772Notes

Reaction equation

HRID 2048772 reaction equation
[Cl-].O[NH3+:3].[C:4](=[O:7])([O-])[OH:5].[Na+].CS(C)=O.[N:13]1([CH2:19][CH2:20][O:21][C@H:22]2[CH2:27][CH2:26][C@H:25]([N:28]3[C:33](=[O:34])[C:32]([CH2:35][C:36]4[CH:41]=[CH:40][C:39]([C:42]5[C:43]([C:48]#[N:49])=[CH:44][CH:45]=[CH:46][CH:47]=5)=[CH:38][CH:37]=4)=[C:31]([CH2:50][CH2:51][CH3:52])[N:30]4[N:53]=[CH:54][N:55]=[C:29]34)[CH2:24][CH2:23]2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C(OCC)(=O)C>[N:13]1([CH2:19][CH2:20][O:21][C@H:22]2[CH2:27][CH2:26][C@H:25]([N:28]3[C:33](=[O:34])[C:32]([CH2:35][C:36]4[CH:41]=[CH:40][C:39]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=5[C:48]5[NH:3][C:4](=[O:7])[O:5][N:49]=5)=[CH:38][CH:37]=4)=[C:31]([CH2:50][CH2:51][CH3:52])[N:30]4[N:53]=[CH:54][N:55]=[C:29]34)[CH2:24][CH2:23]2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 178438648HCID 178438648, compound

Product 1

HCID 178438503HCID 178438503, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of hydroxylammonium chloride (0.54 g), sodium hydrogen carbonate (0.87 g) and dimethyl sulfoxide (10 mL) was stirred at 40° C. for 30 min, 4′-({4-[trans-4-(2-morpholin-4-ylethoxy)cyclohexyl]-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile (0.3 g) was added, and the mixture was stirred at 90° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was dissolved in tetrahydrofuran (10 mL). N,N′-Carbonyldiimidazole (0.1 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.085 mL) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water, and the mixture was adjusted to pH 7 with 1 N hydrochloric acid and extracted with ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.2 g, 59%).

Workup

  1. stirringthe mixture was stirred at 90° C. for 16 hr
  2. washwashed with water
  3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in tetrahydrofuran (10 mL)
  6. additionN,N′-Carbonyldiimidazole (0.1 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.085 mL) were added
  7. stirringthe mixture was stirred at room temperature for 2 hr
  8. additionThe reaction mixture was poured into water
  9. extractionextracted with ethyl acetate
  10. washThe obtained ethyl acetate layer was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d65a1749f76b4e71bd93bd34c7342dfc
Source dataset
uspto-grants-2013_11
Patent number
US08592431B2

Reaction notes

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