Hydrochloric Acid → HCID 178438466, compound

HRID 1412836Notes

Reaction equation

HRID 1412836 reaction equation
[Cl-].O[NH3+].[C:4](=[O:7])([O-])[OH:5].[Na+].[CH3:9][C:10]1[O:14][C:13]([CH2:15][O:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([N:23]3[C:28](=[O:29])[C:27]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([C:37]5[C:38]([C:43]#[N:44])=[CH:39][CH:40]=[CH:41][CH:42]=5)=[CH:33][CH:32]=4)=[C:26]([CH2:45][CH2:46][CH3:47])[N:25]4[N:48]=[CH:49][N:50]=[C:24]34)[CH2:19][CH2:18]2)=[N:12][N:11]=1.[N:51]12CCCN=C1CCCCC2.Cl>O1CCCC1.C(OCC)(=O)C.O.CS(C)=O>[CH3:9][C:10]1[O:14][C:13]([CH2:15][O:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([N:23]3[C:28](=[O:29])[C:27]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=5[C:43]5[NH:51][C:4](=[O:7])[O:5][N:44]=5)=[CH:33][CH:32]=4)=[C:26]([CH2:45][CH2:46][CH3:47])[N:25]4[N:48]=[CH:49][N:50]=[C:24]34)[CH2:19][CH2:18]2)=[N:12][N:11]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 21645Hydroxylamine HClHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 178438603HCID 178438603, compound

Product 1

HCID 178438466HCID 178438466, compoundYield 15%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of hydroxylammonium chloride (0.45 g), sodium hydrogen carbonate (0.72 g) and dimethyl sulfoxide (5 mL) was stirred at 40° C. for 30 min, 4′-[(4-{trans-4-[(5-methyl-1,3,4-oxadiazol-2-yl)methoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (0.24 g) was added, and the mixture was stirred at 90° C. for 15 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 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 tetrahydrofuran (3 mL). N,N′-Carbonyldiimidazole (0.084 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.078 mL) were added, and the mixture was stirred at room temperature for 120 hr. The reaction mixture was diluted with ethyl acetate, adjusted to pH 4 with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic 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 a colorless solid (0.041 g, 15%).

Workup

  1. stirringthe mixture was stirred at 90° C. for 15 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue obtained by silica gel column chromatography
  7. stirringthe mixture was stirred at room temperature for 120 hr
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-86a8b9a4edbd4c2d8f51f9fc3f20d337
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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