Hydrochloric Acid → HCID 15030109, compound

HRID 893271Notes

Reaction equation

HRID 893271 reaction equation
[N:1]1N=N[N:4]2[CH:9]=[C:8]([CH:10]3[O:15][CH2:14][C:13](=[O:16])[N:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11]3)[CH:7]=[CH:6][C:5]=12.O.O.Cl[Sn]Cl.Cl>CO>[NH2:1][C:5]1[N:4]=[CH:9][C:8]([CH:10]2[O:15][CH2:14][C:13](=[O:16])[N:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 15030107HCID 15030107, compound

Product 1

HCID 15030109HCID 15030109, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(tetrazolo[1,5-a]pyrid-6-yl)-4-(1,1-dimethylethyl)-5-oxo-morpholine (550 mg), SnCl2.2H2O (968 mg) and 0.2 ml of 12N hydrochloric acid in 60 ml of methanol was heated at reflux for 14.5 hours under nitrogen. The reaction mixture was concentrated under reduced pressure and then poured into ice water containing 5N sodium hydroxide. The basic aqueous mixture was repeatedly extracted with methylene chloride. The combined organic fractions were washed with water and saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. Concentration gave 603 mg of crude product which was chromatographed on silica gel (95:5:1 methylene chloride:ethanol:ammonium hydroxide) to give 442 mg of product. Mass spectrum (FAB) 250 (M+1). 13C NMR (CDCl3) 27.9 49.5 57.7 69.2 74.3 108.5 123.6 135.8 146.3 158.7 167.4 ppm.

Workup

  1. temperatureat reflux for 14.5 hours under nitrogen
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionpoured into ice water containing 5N sodium hydroxide
  4. extractionThe basic aqueous mixture was repeatedly extracted with methylene chloride
  5. washThe combined organic fractions were washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentration
  8. customgave 603 mg of crude product which
  9. customwas chromatographed on silica gel (95:5:1 methylene chloride:ethanol:ammonium hydroxide)

Sources & evidence

ORD record
ord-02ff2d65a9174adcbf14098464cc99e7
Source dataset
uspto-grants-1992_06
Patent number
US05124328

Reaction notes

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