Ammonium Chloride → 6[[(1,1-dimethylethyl)diphenylsilyl]oxy]-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-1-naphthalenecarboxamide

HRID 1512187Notes

Reaction equation

HRID 1512187 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:8]=[C:9]([NH2:17])[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=2)[CH:6]=1.C[Al](C)C.[CH3:22][C:23]([Si:26]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34]([C:38](OC)=[O:39])=[CH:33][CH:32]=[CH:31]2)([CH3:25])[CH3:24].[NH4+].[Cl-]>C1(C)C=CC=CC=1>[CH3:25][C:23]([Si:26]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34]([C:38]([NH:17][C:9]1[CH:10]=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:12]=[C:7]([N:5]3[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]3)[CH:8]=1)=[O:39])=[CH:33][CH:32]=[CH:31]2)([CH3:22])[CH3:24]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 120028253-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 866414066[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-1-naphthalenecarboxylic acid, methyl ester

Product 1

HCID 685910626[[(1,1-dimethylethyl)diphenylsilyl]oxy]-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-1-naphthalenecarboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere, a stirred solution of 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzenamine (0.99 g, 4.1 mmol) in dry toluene (40 mL) is treated with a solution of AlMe3 (5 mL of 2 M in toluene; 10 mmol) at 40° C. After 45 min, a solution of 6[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-naphthalenecarboxylic acid, methyl ester (1.64 g, 3.72 mmol) in dry toluene (15 mL) is added and the stirred mixture is heated at 100° C. for 90 min. The cooled mixture is then added to a saturated aqueous solution of NH4Cl and stirred for 30 min. The organic phase is separated, washed with brine, dried (Na2SO4) and solvent is evaporated off under reduced pressure to give a residue, which is purified by column chromatography (SiO2; hexane/ethyl acetate 1:1) to afford the title compound as a beige solid.

Workup

  1. customThe organic phase is separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4) and solvent
  4. customis evaporated off under reduced pressure
  5. customto give a residue, which
  6. customis purified by column chromatography (SiO2; hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-8e010fbb9b7447dfa3cbddae30237eb0
Source dataset
uspto-grants-2012_07
Patent number
US08217045B2

Reaction notes

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