Potassium Carbonate → 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl ester

HRID 1643221Notes

Reaction equation

HRID 1643221 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][NH:11][CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:8]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:7]=[C:6]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:2][CH2:3][CH3:4].[O:33]([C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:40]Br)[C:34]([CH3:36])=[O:35].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:48]([O:47][C:45](=[O:46])[C:44]1[CH:43]=[CH:42][C:39]([CH2:40][N:11]([CH2:10][C:9]2[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:7][C:8]=2[C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)=[CH:38][C:37]=1[O:33][C:34](=[O:35])[CH3:36])([CH3:51])([CH3:50])[CH3:49]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 184378533-Acetoxyl-4-tert-butoxycarbonyl-benzyl bromideHCID 58818024[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine

Product 1

HCID 588179794-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine (4.0 g, 9.31 mmol) and 3-acetoxyl-4-tert-butoxycarbonyl-benzyl bromide (3.37 g, 10.24 mmol, 1.1 eq.) in 50 ml anhydrous acetonitrile is added anhydrous potassium carbonate (2.82 g, 20.5 mmol, 2.2 eq.), the resulting mixture is stirred at room temperature for 1 h, then raised to 50° C., stirred overnight. The solid precipitate is filtered off, washed with ethyl acetate, the combined organics is concentrated to dryness, purified through silica gel flash chromatography to give 3.99 g of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]cyclohexylmethyl-amino}-methyl)-2-acetoxy-benzoic acid tert-butyl ester MS (+VE) m/z 680 (M+1).

Workup

  1. temperatureraised to 50° C.
  2. stirringstirred overnight
  3. filtrationThe solid precipitate is filtered off
  4. washwashed with ethyl acetate
  5. concentrationthe combined organics is concentrated to dryness
  6. custompurified through silica gel flash chromatography

Sources & evidence

ORD record
ord-7b025043345248e5b2404c0d43cf4a37
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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