Sodium Hydroxide → HCID 49818908, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed mixture of 2-methyl-2-(4-((4-morpholino-2-(tributylstannyl)thieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)propanamide (150 mg, 0.22 mmol), 3-bromo-2-(methoxymethyl)-1-(phenylsulfonyl)-1H-indole (82 mg, 0.22 mmol), copper(I) thiophene-2-carboxylate (41 mg, 0.22 mmol) in dioxane (2 mL) was added Pd(PPh3)4 (12 mg, 0.011 mmol). The reaction mixture was reacted in the microwave at 140° C. for 35 min. The reaction mixture was filtered through paper and concentrated. The crude product was purified by flash chromatography (20% MeOH in DCM) to give a yellow paste which was dissolved in dioxane (5 mL) and ethanol (1 mL). A 12 M aqueous solution of NaOH was then added. The resulting mixture was then stirred at 65° C. for 15 hours. The reaction mixture was then loaded onto a Biotage Isolute SPE SCX-2 column. The column was washed with MeOH and the desired product was then eluted with 2 M NH3 in MeOH and further purified by RP-HPLC to give 126 (12.4 mg, 10.2%). LCMS: M+H+=564.3. 1H-NMR (400 MHz, DMSO-d6): δ 11.48 (s, 1H), 8.55 (m, 1H), 7.44 (m, 1H), 7.35 (s, 1H), 7.10 (m, 2H), 7.05 (m, 1H), 6.93 (m, 1H), 5.19 (s, 2H), 3.90 (m, 4H), 3.83 (m, 6H), 3.47 (s, 3H), 2.42-2.58 (m, 8H), 1.08 (s, 6H)

Provenance & Evidence