Stannous Chloride → HCID 67924595, compound

HRID 2051493Notes

Reaction equation

HRID 2051493 reaction equation
[CH3:1][C:2]1([NH:5][CH2:6][C@@H:7]([C:9]2[CH:10]=[CH:11][C:12]3[N:13](N=N[N:17]=3)[CH:14]=2)[OH:8])[CH2:4][CH2:3]1.[Cl:18][Sn]Cl>CO.Cl>[ClH:18].[ClH:18].[NH2:17][C:12]1[N:13]=[CH:14][C:9]([C@H:7]([CH2:6][NH:5][C:2]2([CH3:1])[CH2:4][CH2:3]2)[OH:8])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 14988395HCID 14988395, compound

Product 1

HCID 67924595HCID 67924595, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 319 mg (1.37 mmol) of (R)-α-[[(1-methylcyclopropyl)amino]methyl]tetrazolo [1,5-a]pyridine-6-methanol in 25 ml of methanol, 0.12 ml of 12 N HCl and 622 mg (2.75 mmol) of SnCl2 ·2H2O were added. This mixture was heated at reflux for 8 hours and then concentrated to dryness. The residue was partitioned between 80:20 methylene chloride:methanol and 5 ml of 2.5 N NaOH solution. The layers were separated and the aqueous layer repeatedly extracted with 80:20 methylene chloride:methanol. The combined extracts were dried with anhydrous magnesium sulfate and concentrated under reduced pressure, wt. 355 mg. Purification was accomplished by preparative Tlc on silica gel (90:10:1 methylene chloride:methanol:conc. ammonium hydroxide) to give 116 mg of product which was converted into its hydrochloride salt in ethanolic HCl. The salt was precipitated with ether, 105 mg; [α]25D=-28.5 (MeOH, c=1.5); Analysis: Calcd. for C11H17N3O·2HCl:

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 8 hours
  3. concentrationconcentrated to dryness
  4. customThe residue was partitioned between 80:20 methylene chloride
  5. customThe layers were separated
  6. extractionthe aqueous layer repeatedly extracted with 80:20 methylene chloride
  7. dry with materialThe combined extracts were dried with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure, wt. 355 mg
  9. customPurification

Sources & evidence

ORD record
ord-1630a2e4e44745a2a75076f055e2a196
Source dataset
uspto-grants-1991_05
Patent number
US05019578

Reaction notes

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