1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(2,6-Dichlorophenyl)-1H-indole-6-carboxylic acid thiazolo[5,4-b]pyridin-2-ylamide

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Reaction Conditions

Reaction Steps

A mixture of 2-(2,6-dichlorophenyl)-1H-indole-6-carboxylic acid (362 mg, 1.18 mmol), thiazolo[5,4-b]pyridin-2-ylamine (179 mg, 1.18 mmol), EDCI (340 mg, 1.77 mmol) and HOBT (176 mg, 1.30 mmol) in THF (10 mL) was heated in a microwave apparatus at 150° C. for 3 h. The insolubles were filtered off and the filtrate was concentrated under reduced pressure. The residue was chromatographed using a 30-70% gradient of heptane/ethyl acetate to afford the title compound. 1H NMR (DMSO-d6, 400 MHz): δ 12.95 (s, broad, 1H), 12.00 (s, broad, 1H), 8.51 (dd, J=4.7, 1.4 Hz, 1H), 8.34 (s, 1H), 8.16 (d, J=7.7 Hz, 1H), 7.88 (dd, J=8.5, 1.4 Hz, 1H), 7.76 (d, J=8.5 Hz, 1H), 7.68 (d, J=8.3 Hz, 2H), 7.54 (m, 2H), 6.66 (m, 1H). MS (m/z) 439.0 (M+1), Retention time=1.41 min (Method 10). Anal. Calcd.: C, 57.41; H, 2.75; N, 12.75. Found: C, 57.29; H, 2.73; N, 12.54.

Provenance & Evidence