Acetyl chloride → HCID 17754851, compound

HRID 2263983Notes

Reaction equation

HRID 2263983 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:32][CH2:33][CH3:34])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:42](Cl)(=[O:44])[CH3:43]>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([C:42](=[O:44])[CH3:43])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[C@@:13]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)([CH3:24])[N:12]=2)=[C:7]([O:32][CH2:33][CH3:34])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 53628801rac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazole

Product 1

HCID 17754851HCID 17754851, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazole (70 mg, 0.13 mmol, example 2) and triethylamine (92 uL, 0.65 mmol) in methylene chloride (3 mL) was added acetyl chloride (59 uL, Aldrich). The reaction mixture was stirred at room temperature overnight then concentrated. Purification of the crude residue by flash chromatography (12 g of silica gel, eluting with 5-30% ethyl acetate in hexane) gave the title compound (56.1 mg, 80%). HR-MS (ES, m/z) calculated for C31H34N2O2Cl2 [(M+H)+] 537.2070, observed 537.2068.

Workup

  1. concentrationthen concentrated
  2. customPurification of the crude residue
  3. washby flash chromatography (12 g of silica gel, eluting with 5-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b1f8e7425966424598eca5abcb334d13
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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