Dimethyl Sulfoxide → HCID 136052301, compound

HRID 1889505Notes

Reaction equation

HRID 1889505 reaction equation
[Cl-].O[NH3+:3].[C:4](=[O:7])([O-])[OH:5].[Na+].CS(C)=O.[CH2:13]([C:15]1[S:51][C:18]2[N:19]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]4[C:44]([C:49]#[N:50])=[CH:45][CH:46]=[CH:47][CH:48]=4)=[CH:39][CH:38]=3)[C:20](=[O:35])[N:21]([CH2:24][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[O:26])[C:22](=[O:23])[C:17]=2[CH:16]=1)[CH3:14]>C(Cl)(Cl)Cl>[CH2:13]([C:15]1[S:51][C:18]2[N:19]([CH2:36][C:37]3[CH:38]=[CH:39][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=4[C:49]4[NH:3][C:4](=[O:7])[O:5][N:50]=4)=[CH:41][CH:42]=3)[C:20](=[O:35])[N:21]([CH2:24][C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])=[O:26])[C:22](=[O:23])[C:17]=2[CH:16]=1)[CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 59351561HCID 59351561, compound

Product 1

HCID 136052301HCID 136052301, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of hydroxylammonium chloride (8.6 g), sodium hydrogencarbonate (13 g) and dimethyl sulfoxide (100 mL) was stirred at 40° C. for 30 min, 4′-{[6-ethyl-3-[2-(2-methoxyphenyl)-2-oxoethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (4.12 g) was added, and the mixture was stirred at 90° C. for 16 hr. The reaction mixture was diluted with chloroform, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and dissolved in methylene chloride (150 ml). N,N′-Carbonyldiimidazole (1.25 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (1.06 mL) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with chloroform, washed successively with saturated aqueous potassium hydrogensulfate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was recrystallized from chloroform to give the title compound as colorless crystals (1.19 g, 26%).

Workup

  1. stirringthe mixture was stirred at 90° C. for 16 hr
  2. washwashed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. dissolutiondissolved in methylene chloride (150 ml)
  7. additionN,N′-Carbonyldiimidazole (1.25 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (1.06 mL) were added
  8. stirringthe mixture was stirred at room temperature for 2 hr
  9. additionThe reaction mixture was diluted with chloroform
  10. washwashed successively with saturated aqueous potassium hydrogensulfate solution and saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customThe obtained residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-f7d4264eae934960946e35dbadde25a3
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

Loading…