Triethylamine → HCID 17172923, compound

The reaction mixture of 3-(3-endo-amino-8-azabicyclo[3.2.1]octane-8-carbonyl)benzonitrile hydrochloride (300 mg, 1.03 mmol), commercially available 2-(2,4-dichlorophenoxy)-2-methylpropanoic acid (310 mg, 1.24 mmol), EDCI (300 mg, 1.54 mmol), HOBT (210 mg, 1.54 mmol) and triethylamine (0.75 mL, 5.38 mmol) in CH2Cl2 (10 mL) was stirred 18 h. The resulting mixture was washed with satd. aq. NaHCO3 (5 mL) and brine (5 mL) successively, then dried over MgSO4, filtered and evaporated to give a residue which was purified by column chromatography (ethyl acetate: CH2Cl2=1:1) to give N-(8-(3-cyanobenzoyl)-8-azabicyclo[3.2.1]octan-3-endo-yl)-2-(2,4-dichlorophenoxy)-2-methylpropanamide (378 mg, 0.78 mmol, 76% yield) as a white foam. 1H NMR (CDCl3, 400 MHz): δ 1.55 (s, 6H), 1.85 (m, 2H), 2.00 (m, 3H), 2.20 (m, 3H), 2.50 (m, 1H), 4.04 (br s, 1H), 4.28 (q, 1H), 4.86 (br s, 1H), 7.05 (d, 1H), 7.22 (dd, 1H), 7.44 (d, 2H), 7.58 (m, 2H), 7.77 (m, 3H).

1. washThe resulting mixture was washed with satd
2. dry with materialaq. NaHCO3 (5 mL) and brine (5 mL) successively, then dried over MgSO4
3. filtrationfiltered
4. customevaporated
5. customto give a residue which
6. customwas purified by column chromatography (ethyl acetate: CH2Cl2=1:1)

ORD record

ord-1854896a56c74a87873d3023fcddc67e

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163771B2