1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59146050, compound

Participants

Reaction Steps

HOBT (211 mg) and EDCI (260 mg) were added to a solution of 5-chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylic acid (148 mg) in THF (4 mL). The resulting solution was stirred for 1 hour. Ethyl 3-{5-fluoro-7-[(Z)-(hydroxyamino)(imino)methyl]-1H-indol-3-yl}propanoate (D136) (302 mg) in THF (4 mL) was added, and the reaction mixture was stirred at RT for 1.5 hours. TBAF (780 mg) was then added. The reaction vessel was sealed and heated in Biotage Initiator using initial normal to 120° C. for 1.5 hours. After cooling, the reaction was quenched with water, and extracted with EA for 3 times. The combined organic solution was washed with brine, and dried over anhydrous sodium sulfate. The dried solution was concentrated. The residue was purified by column chromatography to afford ethyl 3-[7-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoate (D139) (341 mg) as a pale yellow solid. δH (CDCl3, 400 MHz): 1.26 (3H, t), 1.47 (6H, d), 2.73 (2H, t), 3.12 (2H, t), 4.15 (2H, q), 5.52 (1H, m), 7.24 (1H, d), 7.47 (1H, dd), 7.86 (1H, dd), 8.43 (1H, d), 8.93 (1H, d), 9.54 (1H, br s). MS (ES): C23H22ClFN4O4 requires 472; found 473.2 (M+H+).

Provenance & Evidence