Diisopropylethylamine → 1,1-dimethylethyl(2S)-2-{[(2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-5-yl)amino]carbonyl}-1-pyrrolidinecarboxylate

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Reaction Steps

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) was treated with 1-{[(1,1-dimethylethyl)oxy]carbonyl}-L-proline (0.022 g, 0.103 mmol), DIPEA (0.090 mL, 0.514 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.079 g, 0.309 mmol) as in the general procedure described herein. The crude product was purified by silica gel chromatography (hexanes/ethyl acetate) to afford the title compound (0.035 g, 51%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.51 (s, 1H), 9.77 (s, 1H), 8.95 (s, 1H), 7.88-7.98 (m, 1H), 7.77 (s, 1H), 7.44 (s, 3H), 7.33-7.40 (m, 1H), 7.27-7.33 (m, 1H), 7.19-7.26 (m, 1H), 7.07 (s, 1H), 4.52 (s, 2H), 4.15 (m, 1H), 3.24-3.45 (m, 2H), 2.14 (m, 1H), 1.62-1.92 (m, 3H), 1.36 (s, 3H), 1.23 (s, 6 H). MS: m/z 666 (M+1).

Provenance & Evidence