Cesium carbonate → HCID 50939922, compound

Participants

Reaction Conditions

Reaction Steps

2-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl 4-methylbenzenesulfonate from step 1 of Example 5 (100 mg, 0.23 mmol) was dissolved in NMP (1.1 ml). The mixture of tert-butyl [1-(4-methoxybenzyl)-1H-indazol-5-yl]carbamate and tert-butyl [1-(4-methoxybenzyl)-2H-indazol-5-yl]carbamate (81 mg, 0.23 mmol) from step 2 of this example and cesium carbonate (0.224 mg, 0.69 mmol) were added and the slurry stirred at 70° C. for 24 h. The mixture was diluted with 4:1 water:saturated sodium bicarbonate (30 ml), extracted with EtOAc (3×30 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered, and the volatiles removed in vacuum. The material was dissolved in TPA at RT and the solution stirred for 5 minutes. The solution was heated to 70° C. for 2 hours. The volatiles were removed in vacuum. The residue was dissolved in DCM (30 ml), shaken with a solution of saturated bicarbonate (30 ml), the layers separated, and the aqueous phase extracted with DCM (2×30 ml). The organic fractions were combined, washed with brine, dried over Na2SO4, filtered, and the volatiles removed in vacuum. The product was purified by chromatography on SiO2 eluting with 20% acetone:DCM to give the titled compound. LRMS calc: 396.18; obs: 397.27 (M+1). Compounds reported in Table 6 are prepared by a general procedure analogous to that described in Example 42 above.

Provenance & Evidence