Triethylamine → HCID 86703244, compound

Participants

Reaction Steps

Methanesulfonic anhydride (3.42 g, 19.62 mmol) was added at −40° C. to a stirred solution of methyl 2-((4-chlorophenyl)(hydroxy)methyl)-1-cyclopropyl-1H-pyrrole-3-carboxylate (Step 240.5) (3 g, 9.81 mmol) and triethylamine (6.84 mL, 49.1 mmol) in CH2Cl2 (60 mL). After 15 min at −40° C., 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 240.7) (1.762 g, 12.76 mmol) was added. The resulting mixture was allowed to warm from −40° C. to rt over 18 hr under stirring, diluted in CH2Cl2//water, and extracted twice with CH2Cl2. The combined organic extracts were dried and concentrated. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 97.5:2.5) to afford the title compound (2.2 g, 51.6% yield) as a brown foam. tR: 1.13 min (LC-MS 6); ESI-MS: 426.2 [M+H]+ (LC-MS 6); TLC (CH2Cl2/MeOH 97.5:2.5): Rf=0.29.

Provenance & Evidence