Triethylamine → N-Cycloheptyl-N-(2,2-dimethoxyethyl)-3-(3-(1-methyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanamide

Temperature

25 °C

A solution of T3P (1.656 mL) dissolved in THF (1.57M) was added in one portion to a stirred solution of N-(2,2-dimethoxyethyl)cycloheptanamine (0.30 mL), 3-(3-(1-methyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoic acid [Example 5, Step ii)] (0.51 g) and triethylamine (2.17 mL) in acetonitrile (5 mL) at 25° C. The resulting solution was stirred at 25° C. for 15 min. The reaction mixture was diluted with ethyl acetate (100 mL), and washed with saturated sodium hydrogen carbonate (50 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0-70% ethyl acetate in isohexane to afford the subtitled compound (0.51 g). 1H NMR (400 MHz, CD3OD) δ 8.25 and 8.24 (2×s, 1H), 7.68-7.65 (m, 1H), 7.62 (d, J=7.9 Hz, 1H), 7.32 and 7.31 (2×t, J=7.6 Hz, 1H), 7.20 (d, J=7.3 Hz, 1H), 4.56 and 4.39 (2×t, J=5.1 Hz, 1H), 4.13 (s, 3H), 3.85-3.66 (m, 5H), 3.36-3.32 (m, 2H), 3.34 (s, 3H), 3.32 (s, 3H), 3.22 (d, J=5.0 Hz, 2H), 2.92-2.85 (m, 2H), 2.63 and 2.60 (2×t, J=6.0 Hz, 2H), 1.83-1.32 (m, 10H), a ˜1:1 mixture of rotamers is observed.

1. washwashed with saturated sodium hydrogen carbonate (50 mL)
2. dry with materialThe organic layer was dried over magnesium sulfate
3. filtrationfiltered
4. customevaporated
5. customto afford crude product
6. customThe crude product was purified by flash silica chromatography, elution gradient 0-70% ethyl acetate in isohexane

ORD record

ord-c7f5b9de2e4d4e868dd7a7c01ee7b5a4

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017602B2