Einecs 211-027-4 → HCID 178464705, compound

HRID 480480Notes

Reaction equation

HRID 480480 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]([OH:44])([C:20]3[N:21]=[CH:22][N:23](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:24]=3)[CH:17]([CH3:19])[CH3:18])[CH:12]=2)[CH:7]=1)=[O:5])[CH3:2].[Cl-].[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH2:1]([NH:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:16]([OH:44])([C:20]3[N:21]=[CH:22][NH:23][CH:24]=3)[CH:17]([CH3:19])[CH3:18])[CH:12]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 69401Einecs 211-027-4HCID 516892Sodium BicarbonateHCID 18769117N-ethyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthamide

Product 1

HCID 178464705HCID 178464705, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-ethyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthamide (11.5 g) and pyridinium chloride (4.62 g) in methanol (60 mL) was stirred at 60° C. for 2 h. The mixture was neutralized with sodium bicarbonate solution and concentrated. The residue was dissolved in ethanol and insoluble material was filtered off. The filtrate was concentrated and purified by column chromatography (eluent; dichloromethane:methanol=10:1→7:1) to give the titled compound (5.75 g) as a colorless powder.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethanol
  3. filtrationinsoluble material was filtered off
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography (eluent; dichloromethane:methanol=10:1→7:1)

Sources & evidence

ORD record
ord-33df7664786f4a7caa5d9d41855d9caf
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

Loading…