Dimethyl Sulfoxide → HCID 136052396, compound

HRID 1889557Notes

Reaction equation

HRID 1889557 reaction equation
[Cl-].O[NH3+:3].[C:4](=[O:7])([O-])[OH:5].[Na+].CS(C)=O.[CH3:13][C:14]1([CH3:52])[CH2:18][C:17]2[CH:19]=[C:20]([N:23]3[C:28](=[O:29])[C:27]4[CH:30]=[C:31]([CH2:33][CH3:34])[S:32][C:26]=4[N:25]([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][C:37]=4[F:50])[C:24]3=[O:51])[CH:21]=[CH:22][C:16]=2[O:15]1>O>[CH3:52][C:14]1([CH3:13])[CH2:18][C:17]2[CH:19]=[C:20]([N:23]3[C:28](=[O:29])[C:27]4[CH:30]=[C:31]([CH2:33][CH3:34])[S:32][C:26]=4[N:25]([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][C:37]=4[F:50])[C:24]3=[O:51])[CH:21]=[CH:22][C:16]=2[O:15]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 59351604HCID 59351604, compound

Product 1

HCID 136052396HCID 136052396, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of hydroxylammonium chloride (1.2 g), sodium hydrogencarbonate (1.6 g) and dimethyl sulfoxide (10 mL) was stirred at 40° C. for 30 min, 4′-{[3-(2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-6-ethyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}-3′-fluorobiphenyl-2-carbonitrile (0.54 g) was added, and the mixture was stirred at 90° C. for 16 hr. To the reaction mixture was added water, and the precipitated solid was collected by filtration, washed with water, and dried under reduced pressure. The solid was dissolved in tetrahydrofuran (10 mL), N,N′-carbonyldiimidazole (0.24 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.22 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 purified by silica gel column chromatography to give the title compound as a pale-yellow solid (0.43 g, 72%).

Workup

  1. stirringthe mixture was stirred at 90° C. for 16 hr
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure
  5. dissolutionThe solid was dissolved in tetrahydrofuran (10 mL)
  6. additionN,N′-carbonyldiimidazole (0.24 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.22 mL) were added
  7. stirringthe mixture was stirred at room temperature for 2 hr
  8. additionThe reaction mixture was diluted with chloroform
  9. washwashed successively with saturated aqueous potassium hydrogensulfate solution and saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-64dfb6cf6be149fe852f6e6844c79113
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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