Triethylamine → HCID 178513546, compound

Participants

Reaction Conditions

Reaction Steps

This compound was prepared in a fashion analogous to the procedure described in Example 16. Thus, 5-(3-fluorophenyl)-3-(4-piperidinyl)-1H-indazole-7-carboxamide (Intermediate 15) (75 mg, 0.167 mmol) was reacted with 2-chloro-1-ethanesulfonyl chloride (17 uL, 0.167 mmol) in the presence of triethyl amine (93 uL, 0.665 mmol) in DMF (2 mL) at 0° C. After 10 mins, K2CO3 (46 mg, 0.334 mmol) and pyrrolidine (41 uL, 0.501 mmol) were added. The reaction mixture was heated to 100° C. overnight. The resulting suspension was filtered. The filtrate was concentrated and the residue was purified by using a Gilson semi-preparative HPLC system, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to afford the title compound (12.6 mg, 15% for 2 steps).

Provenance & Evidence