Dichloromethane → HCID 118413252, compound

Participants

Reaction Conditions

Reaction Steps

Isobutylene oxide (17 μl, 0.191 mmol) was added to a stirred solution of (3R,3aR,6R,6aR)-6-[1-allyl-6-chloro-5-[4-(5,6-dihydro-4H-pyrrolo[3,4-c]pyrazol-2-yl)phenyl]imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (83.4 mg, 0.160 mmol) in dioxane (0.64 ml). The reaction mixture was a pale yellow solution that was heated to 80° C. After 3 days, additional isobutylene oxide (8 μl, 0.090 mmol) was added. After stirring an additional 16 h, the reaction mixture was cooled to room temperature. The reaction mixture was then diluted with MeOH/DCM and loaded onto two 500 micron 20 cm×20 cm silica gel plates, which were developed twice using 10% (10% NH4OH/MeOH)/DCM. The silica containing the product band was collected and eluted with 10% (10% NH4OH/MeOH)/DCM (80 ml). The solvent was evaporated under reduced pressure to give the desired product as a yellow residue. LC-MS: calculated for C30H33ClN6O5 592.22 observed m/e: 593.25 (M+H)+ (Rt 1.00/2 min)

Provenance & Evidence