Water → HCID 57504292, compound

Participants

Reaction Steps

A solution of 2-bromo-4-(2-methoxyethoxy)-N-(4-methyl-1,3-thiazol-2-yl)butanamide (104 mg, 0.308 mmol) in DMF (1 mL) was added to a stirred solution of 1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine-4-thiol (81.0 mg, 0.308 mmol) and K2CO3 (51.1 mg, 0.370 mmol) in DMF (2 mL). The reaction mixture was kept at ambient temperature for 3 hrs (45° C. and 17 hrs for example 54, 55 and 56). Water and EtOAc were added, and the two phases were separated. The aqueous phase was extracted with EtOAc. The organic extracts were combined and washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with DCM/EtOAc:1/1) to give the title compound as a colourless viscous oil (145 mg), 1H NMR (300 MHz, CDCl3) δ 11.06 (br s, 1H), 8.93 (s, 1H), 8.30 (s, 1H), 7.62 (m, 1H), 7.49 (m, 3H), 6.51 (s, 1H), 5.14 (t, 1H), 3.77 (m, 1H), 3.67 (m, 1H), 3.59 (m, 2H), 3.50 (m, 2H), 3.33 (s, 3H), 2.60 (m, 1H), 2.27 (m, 4H), HRMS: calcd for (M+H+) C22H2435ClN6O3S2: 518.1040. Found: 519.1050.

Provenance & Evidence