Triethylamine → HCID 22613814, compound

HRID 844576Notes

Reaction equation

HRID 844576 reaction equation
[N:1]1([CH2:6][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.[CH3:32][O:33][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37]>C(#N)C>[CH3:32][O:33][C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[C:36]([C:2]1[N:1]([CH2:6][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:4][N:3]=1)=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 226138011-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane

Product 1

HCID 22613814HCID 22613814, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(Imidazol-1-yl)-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane (0.86 g) (see Preparation 30) and triethylamine (1.3 ml) were dissolved in acetonitrile (15 ml), under a nitrogen atmosphere, the solution cooled in an ice-bath and 2-methoxybenzoyl chloride (1.4 ml) added, dropwise. The mixture was allowed to warm to room temperature slowly and then stirred for 2 days. The acetonitrile was removed under reduced pressure and the residue dissolved in dichloromethane (20 ml) and washed sequentially with water and brine. The organic phase was then dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give a residue which was chromatographed on silica gel eluting with 97:3, by volume, dichloromethane:methanol to give 1-[2-(2-methoxybenzoyl)imidazol- 1-yl]-2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butane (1.1 g) as an oil and as a mixture of diastereomers.

Workup

  1. temperaturethe solution cooled in an ice-bath
  2. customThe acetonitrile was removed under reduced pressure
  3. dissolutionthe residue dissolved in dichloromethane (20 ml)
  4. washwashed sequentially with water and brine
  5. dry with materialThe organic phase was then dried over anhydrous sodium sulphate
  6. customthe solvent removed under reduced pressure
  7. customto give a residue which
  8. customwas chromatographed on silica gel eluting with 97:3, by volume, dichloromethane

Sources & evidence

ORD record
ord-d4d034a2503047a7a17448ae1f2b67a7
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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