Hydrochloric Acid → {2-[(1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acid

Participants

Reaction Conditions

Reaction Steps

Following general procedure A using 6-fluoroindole and R5X=cyclopropyl-methylbromide {2-[(1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acid ethyl ester was obtained. Ester hydrolysis: 110 mg (0.25 mmol) {2-[(1-cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acid ethyl ester was dissolved in EtOH (3 mL) and NaOH (254 μL, 4N) was introduced. The mixture was heated to 80° C. for 1 hour before it was cooled to room temperature and pH was adjusted to 2 using 1 N HCl, where-upon a white precipitate was formed. The product was filtered off and dried to give 85 mg {2-[(1-Cyclopropylmethyl-6-fluoro-1H-indole-3-carbonyl)-amino]-thiazol-4-ylsulfanyl}-acetic acid.

Provenance & Evidence