Sodium Carbonate → HCID 21180465, compound

HRID 1386936Notes

Reaction equation

HRID 1386936 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[N:16]([CH2:17][C:18](=[O:20])[CH3:19])[N:15]=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:13]=2)[CH:9]=[CH:10][CH:11]=1)[CH3:4].[BH4-].[Li+].C([O-])([O-])=O.[Na+].[Na+].Cl.CCO>CO.C(Cl)(Cl)Cl.CCOCC>[ClH:1].[CH3:2][N:3]([CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[N:16]([CH2:17][CH:18]([OH:20])[CH3:19])[N:15]=[C:14]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[N:13]=2)[CH:9]=[CH:10][CH:11]=1)[CH3:4]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 4148881Lithium borohydrideHCID 21180474HCID 21180474, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 21180465HCID 21180465, compoundYield 84.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 1-[5-(3-dimethylaminomethyl-phenyl)-3-(4-methoxy-phenyl)-[1,2,4]triazol-1-yl]-propan-2-one hydrochloride (22 mg, 0.05 mmol) in methanol (4 ml), was added Lithium borohydride (1.8 mg, 0.08 mmol) and the mixture stirred for 4 hr at r.t. Saturated Na2CO3 solution was then added and the mixture stirred for 15 min., the aqueous phase was then extracted twice with EtOAc, dried with Na2SO4 filtered and the solvent evaporated to afford a yellow oil. This was dissolved in CHCl3 and 1.45N HCl/EtOH (0.05 ml) was added at 4° C. After 20 min ether was added to precipitate the titled salt as a light brown solid (17 mg, 76.9% yield) MS: m/e=367.3 (M+H+).

Workup

  1. stirringthe mixture stirred for 15 min.
  2. extractionthe aqueous phase was then extracted twice with EtOAc
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customto afford a yellow oil

Sources & evidence

ORD record
ord-114bcebc98564b2aa8575037693a3e23
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

Loading…