1,1,1-Trimethoxybutane → HCID 21912893, compound

HRID 1008063Notes

Reaction equation

HRID 1008063 reaction equation
Cl.N1C=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]1[C:20]([CH3:21])=[C:19]([CH3:22])[N:18]=[C:17]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]=1[NH2:30].COC(OC)(OC)CCC>C1(C)C=CC=CC=1>[Cl:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:15]2[C:20]([CH3:21])=[C:19]([CH3:22])[N:18]=[C:17]([O:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:16]=2[N:30]=[C:3]1[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 1235121,1,1-TrimethoxybutaneHCID 10176127Pyridinium chlorideHCID 85898859HCID 85898859, compound

Product 1

HCID 21912893HCID 21912893, compoundYield 219.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, pyridine hydrochloride (4.2 g, 36.4 mmol) was added in small amounts to a solution of N4-(5-chloropentyl)-5,6-dimethyl-2-phenoxypyridine-3,4-diamine (32.4 g, 97.0 mmol) in toluene (500 mL). Trimethylorthobutyrate (17 mL, 107 mmol) was then added, and the reaction was heated at reflux for two hours. The solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate (500 mL). The solution was washed with water (3×80 mL) and brine (1×40 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford an oil, which was dissolved in hexanes (20 mL) and concentrated under reduced pressure to provide an off-white solid. The crude solid was purified by column chromatography on silica gel (eluting with 2:1 hexane:ethyl acetate) to provide 30.8 g of 1-(5-chloropentyl)-6,7-dimethyl-4-phenoxy-2-propyl-1H-imidazo[4,5-c]pyridine as white crystals.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for two hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate (500 mL)
  5. washThe solution was washed with water (3×80 mL) and brine (1×40 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford an oil, which
  10. concentrationconcentrated under reduced pressure
  11. customto provide an off-white solid
  12. customThe crude solid was purified by column chromatography on silica gel (eluting with 2:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-0abdaa7dbead41ecb1e60db196ca3435
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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