Triethylamine → HCID 17172923, compound

A mixture of 3-((3-endo-amino-8-azabicyclo[3.2.1]octan-8-yl)methyl)benzonitrile dihydrochloride (470 mg, 1.49 mmol), commercially available 2-(2,4-dichlorophenoxy)-2-methylpropanoic acid (4) (447 mg, 1.79 mmol), EDCI (430 mg, 2.24 mmol), HOBT (304 mg, 2.24 mmol) and triethylamine (1.3 mL, 9.32 mmol) in CH2Cl2 (5 mL) was stirred 18 h. The resulting mixture was washed with satd. aq. NaHCO3 solution (5 mL), brine (5 mL) successively, 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-cyanobenzyl)-8-azabicyclo[3.2.1]octan-3-endo-yl)-2-(2,4-dichlorophenoxy)-2-methylpropanamide (526 mg, 1.11 mmol, 74% yield) as a solid. 1H NMR (CDCl3, 400 MHz): δ 1.55 (s, 6H), 1.65 (d, 2H), 1.85 (m, 2H), 2.08 (m, 2H), 2.25 (m, 2H), 3.15 (br s, 2H), 3.55 (ABq, 2H), 4.17 (m, 1H), 7.04 (d, 1H), 7.20 (dd, 1H), 7.44 (m, 2H), 7.48 (m, 1H), 7.54 (m, 1H), 7.62 (d, 1H), 7.70 (br s, 1H).

1. washThe resulting mixture was washed with satd
2. dry with materialaq. NaHCO3 solution (5 mL), brine (5 mL) successively, 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-39538d828f1641108485e5e906963ae9

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163771B2