Einecs 211-027-4 → HCID 178450069, compound

HRID 480485Notes

Reaction equation

HRID 480485 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:17]([OH:45])([C:21]4[N:22]=[CH:23][N:24](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:25]=4)[CH:18]([CH3:20])[CH3:19])[CH:13]=3)[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[Cl-].[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH:1]1([NH:4][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:17]([OH:45])([C:21]4[N:22]=[CH:23][NH:24][CH:25]=4)[CH:18]([CH3:20])[CH3:19])[CH:13]=3)[CH:8]=2)=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 69401Einecs 211-027-4HCID 516892Sodium BicarbonateHCID 18769022N-cyclopropyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthamide

Product 1

HCID 178450069HCID 178450069, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-cyclopropyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthamide (16.0 g) and pyridinium chloride (6.46 g) in methanol (84 mL) was heated at 60° C. for 3 h. The mixture was neutralized with sodium bicarbonate solution. The solvent was evaporated and the residue was dissolved in ethanol and insoluble material was filtered off. The filtrate was concentrated and purified by column chromatography (eluent; CHCl3: 8% methanolic ammonia=19:1→9:1) to give the titled compound (8.9 g) as a colorless powder.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethanol
  3. filtrationinsoluble material was filtered off
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography (eluent; CHCl3: 8% methanolic ammonia=19:1→9:1)

Sources & evidence

ORD record
ord-314b47e8205c4fd99e0b721052acf9d6
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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