Hydroxylamine HCl → HCID 136052353, compound

HRID 1889546Notes

Reaction equation

HRID 1889546 reaction equation
[Cl-].O[NH3+].[C:4](=[O:7])([O-])[OH:5].[Na+].[CH2:9]([O:11][C:12]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)[C:15]2[S:32][C:33]([CH2:35][CH3:36])=[CH:34][C:14]=2[N:13]=1)[CH3:10].[N:37]12CCCN=C1CCCCC2>C(Cl)(Cl)Cl.C(Cl)Cl.CS(C)=O>[CH2:9]([O:11][C:12]1[N:16]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[NH:37][C:4](=[O:7])[O:5][N:31]=3)=[CH:22][CH:23]=2)[C:15]2[S:32][C:33]([CH2:35][CH3:36])=[CH:34][C:14]=2[N:13]=1)[CH3:10]

Participants

8

Reactant 4

HCID 21645Hydroxylamine HClHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 59351576HCID 59351576, compound

Product 1

HCID 136052353HCID 136052353, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of hydroxylammonium chloride (0.74 g), sodium hydrogencarbonate (1.07 g) and dimethyl sulfoxide (20 mL) was stirred at 40° C. for 30 min, 4′-[(2-ethoxy-5-ethyl-3H-thieno[2,3-d]imidazol-3-yl)methyl]biphenyl-2-carbonitrile (0.48 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 obtained by silica gel column chromatography was dissolved in methylene chloride (20 mL), N,N′-carbonyldiimidazole (0.22 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.18 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 precipitated solid was collected by filtration to give the title compound as colorless crystals (0.33 g, 59%).

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 obtained by silica gel column chromatography
  6. stirringthe mixture was stirred at room temperature for 2 hr
  7. washwashed successively with saturated aqueous potassium hydrogensulfate solution and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-92a9c21abdb2433b9e8b02a82c486f84
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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