Triethylamine → HCID 53734757, compound

HRID 2187612Notes

Reaction equation

HRID 2187612 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](=O)[CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)=[CH:22][CH:21]=1.C(N(CC)CC)C.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>ClCCl.CO.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([NH:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:3]=2)[CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)=[CH:22][CH:21]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 51512791-(4-fluorophenyl)-2-(1H-imidazol-1-yl)ethan-1-oneHCID 18476027HCID 18476027, compound

Product 1

HCID 53734757HCID 53734757, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 160960Diamminetetrachlorotitanate(IV)CatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Titanium chloride (2.86 ml; 26 mmol) was added portionwise to a solution of methyl 4-amino-2-(4-fluorophenyl)benzoate (5 g; 20 mmol), 1-(4-fluorophenyl)-2-(imidazol-1-yl) ethanone (4.08 g; 20 mmol) and triethylamine (8.4 ml; 60 mmol) in dichloromethane (120 ml) at 0° C. under argon atmosphere. After stirring overnight at ambient temperature, sodium cyanoborohydride (1.4 g; 0.22 mmol) in solution in methanol (10 ml) was added at 0° C. The reaction mixture was stirred for 2 hours at ambient temperature, treated with 5% aqueous sodium hydrogen carbonate solution, filtered and extracted with dichloromethane. After evaporation to dryness of the organic phase, the residue was purified by flash chromatography eluting with dichloromethane/ethanol 95/5 to give methyl 4-[1-(4-fluorophenyl)-2-(imidazol-1-yl)ethylamino]-2-(4-fluorophenyl)benzoate. Yield 52%.

Workup

  1. stirringThe reaction mixture was stirred for 2 hours at ambient temperature
  2. filtrationfiltered
  3. extractionextracted with dichloromethane
  4. customAfter evaporation to dryness of the organic phase
  5. customthe residue was purified by flash chromatography
  6. washeluting with dichloromethane/ethanol 95/5

Sources & evidence

ORD record
ord-df3c8ec8df954fa1aee550a7315bab36
Source dataset
uspto-grants-2002_06
Patent number
US06410539B1

Reaction notes

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