Triethylamine → N'-heptyl-N-(2,4,6-trifluorophenyl)-N'-[[2'-[N-(triphenylmethyl)tetrazol-5-yl]-1,1'-biphenyl-4-yl]methyl]urea

2,4,6-Trifluorobenzoic acid (148.8 mg), diphenylphosphoryl azide (223.3 mg) and triethylamine (105.1 mg) were added to benzene (8 mL) and the mixture was heated under reflux. Fifty minutes later, a solution of N-heptyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (393.7 mg) in benzene (3 mL) was added to the reaction mixture, and under reflux, heating was continued. Upon elapsed time of 45 minutes after the addition of the solution, the reaction mixture was concentrated under reduced pressure. Ethyl acetate (40 mL) was added to the residue, and the resulting mixture was washed successively with 5% hydrochloric acid, water, a saturated sodium bicarbonate solution and brine (40 mL, each). The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (hexane/ethyl acetate) to afford N′-heptyl-N-(2,4,6-trifluorophenyl)-N′-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]urea as a colorless amorphous mass (369.1 mg).

1. temperaturethe mixture was heated
2. temperatureunder reflux
3. temperatureunder reflux
4. temperatureheating
5. additionUpon elapsed time of 45 minutes after the addition of the solution
6. concentrationthe reaction mixture was concentrated under reduced pressure
7. additionEthyl acetate (40 mL) was added to the residue
8. washthe resulting mixture was washed successively with 5% hydrochloric acid, water
9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-b98e816bba8844feb006a99d8dff52de

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531576B2