Diisopropylethylamine → 3-{2-[5-(4-aminothieno[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}benzonitrile

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Reaction Steps

To a 4 mL screw cap vial was added 3-(2,3-dihydro-1H-indol-5-yl)thieno[3,2-c]pyridin-4-amine (100 mg, 0.329 mmol) followed by HATU (125 mg, 0.329 mmol), 3-cyanophenylacetic acid (53.0 mg, 0.329 mmol) and DIEA (0.230 mL, 1.317 mmol). N,N-Dimethylformamide (DMF) (2 mL) was added and the reaction was sealed and left to stir at room temperature overnight. The reaction mixture was poured into water (4 mL) and extracted with EtOAc (5 mL). The organics were dried over Na2SO4 and concentrated. The residue was taken up in DCM and purified via normal phase chromatography (0-10% MeOH/DCM). Fractions were collected and concentrated to afford 3-{2-[5-(4-aminothieno[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}benzonitrile (100.8 mg). 1H NMR (400 MHz, DMSO-d6) d ppm 8.13 (d, J=8.1 Hz, 1H) 7.83 (d, J=5.8 Hz, 1H) 7.73-7.79 (m, 2H) 7.66 (d, J=7.8 Hz, 1H) 7.52-7.61 (m, 1H) 7.44 (s, 1H) 7.35 (s, 1H) 7.28 (d, J=5.6 Hz, 1H) 7.20-7.26 (m, 1H) 5.48 (br. s., 2H) 4.29 (t, J=8.5 Hz, 2H) 4.00 (s, 2H) 3.27 (t, 2H).

Provenance & Evidence