Hydrochloric Acid → HCID 14747879, compound

HRID 1164899Notes

Reaction equation

HRID 1164899 reaction equation
[CH3:1][C:2]([NH:13][CH2:14][C@@H:15]([C:17]1[CH:18]=[CH:19][C:20]2[N:21](N=N[N:25]=2)[CH:22]=1)[OH:16])([CH3:12])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.[ClH:26]>CO>[ClH:26].[ClH:26].[NH2:25][C:20]1[N:21]=[CH:22][C:17]([C@H:15]([CH2:14][NH:13][C:2]([CH3:12])([CH3:1])[CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=2)[OH:16])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18637941HCID 18637941, compound

Product 1

HCID 14747879HCID 14747879, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 137 mg (0.40 mmol) of (R)-a-[[(1,1-dimethyl-3-(3-hydroxyphenyl)propyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol and 182 mg (0.81 mmol) of SnCl2 ·H2O in 20 ml of methanol was heated at reflux for 21 hours. The reaction mixture was cooled in an ice bath and H2S was bubbled through the solution. The precipitate was removed by filtration and the filtrate concentrated. The residue was chromatographed on silica gel (94:6:2 CH2Cl2 :MeOH:NH4OH) to give pure product which was converted into its hydrochoride salt with ethanolic HCl, 97.3 mg, [a]D =-17.3° C.

Workup

  1. temperatureat reflux for 21 hours
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. customH2S was bubbled through the solution
  4. customThe precipitate was removed by filtration
  5. concentrationthe filtrate concentrated
  6. customThe residue was chromatographed on silica gel (94:6:2 CH2Cl2 :MeOH:NH4OH)
  7. customto give pure product which

Sources & evidence

ORD record
ord-ff6395df7bff42bcb0da317cc8336a9c
Source dataset
uspto-grants-1990_03
Patent number
US04906645

Reaction notes

Loading…