HCID 10236495, compound → HCID 10192891, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 98 (0.56 g) and Pyr-HCl and heated at 200° C. for 1 h (while occasionally adding more Pyr-HCl). The reaction was allowed to cool and then partitioned between 2 N HCl aq and EtOAc. A small amount of MeOH was added to facilitate the dissolution process. The organic layer was washed with saturated NaHCO3 aq, brine, and dried over MgSO4. Filtration, concentration and trituration of the pdt with CH2Cl2 yielded 0.44 g of the desired pdt which contained some inorganic impurities. The material was then chromatographed on silica gel (MeOH/CH2Cl2 1:19 to MeOH/CH2Cl2 1:9) to yield 0.24 g of 99: Mp=236-237° C.; 1H NMR (DMSO-d6) δ 10.06 (br s, 1 H), 7.73 (d, 2 H, J=8.3 Hz), 7.46 (dd, 1 H, J=2.4 Hz, 0.7 HZ), 7.38 (dd, 1 H, J=2.3 Hz, 0.7 Hz), 7.28 (s, 1 H), 6.93 (d, 2 H, J=8.3 Hz); MS 270 (M−H)−.

Provenance & Evidence