Diisopropylethylamine → HCID 86644906, compound

Participants

Reaction Steps

BOP chloride (0.079 g, 0.309 mmol) was added to a solution of 5-amino-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamide trifluoroacetate (0.060 g, 0.103 mmol), 3-(1-piperidinyl)propanoic acid (0.0162 g, 0.103 mmol) and diisopropylethylamine (0.090 mL, 0.514 mmol) in DMF (1 mL). The mixture was stirred at room temperature for 1 hr. The reaction mixture was extracted with ethyl acetate and water. The organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was purified by reverse phase HPLC (acetonitrile:water with 0.% trifluoroacetic acid) to give 0.032 g (43%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (br. s., 1H), 10.01 (br. s., 1H), 9.01-9.18 (m, 1H), 8.97 (d, 1H), 7.92 (br. s., 1H), 7.68-7.84 (m, 1H), 7.40-7.56 (m, 2H), 7.27-7.41 (m, 2H), 7.15-7.28 (m, 1H), 7.08 (s, 1H), 4.36-4.68 (m, 2H), 3.22-3.48 (m, 4H), 2.67-2.98 (m, 4H), 1.72-1.87 (m, 2H), 1.48-1.71 (m, 3H), 1.20-1.43 (m, 1H). ES MS: m/z 608 (M+1).

Provenance & Evidence