Dimethyl Sulfoxide → HCID 178517717, compound

A solution of 2-(4-fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine (Preparation #4, 0.050 g, 0.14 mmol), 3-aminoquinuclidine dihydrochloride (0.054 g, 0.27 mmol), DIEA (0.047 mL, 0.27 mmol), and DMSO (1 mL) were shaken at about 80° C. for about 24 h. Additional DIEA (0.100 mL) was added to the mixture. The mixture was concentrated in vacuo to remove DMSO. The material was treated with saturated solution of NaHCO3 (30 mL) and EtOAc (50 mL). The layers were separated, and the aqueous layer was washed sequentially with EtOAc (3×50 mL) and DCM (50 mL). The combined organic layers were dried over MgSO4 and concentrated. The mixture was triturated in EtOAc and filtered to yield the title compound (0.007 g, 20%): LC/MS (Table 1, Method b) Rt=1.3 min; MS m/z: 308.2 (M+H)+.

1. concentrationThe mixture was concentrated in vacuo
2. customto remove DMSO
3. additionThe material was treated with saturated solution of NaHCO3 (30 mL) and EtOAc (50 mL)
4. customThe layers were separated
5. washthe aqueous layer was washed sequentially with EtOAc (3×50 mL) and DCM (50 mL)
6. dry with materialThe combined organic layers were dried over MgSO4
7. concentrationconcentrated
8. customThe mixture was triturated in EtOAc
9. filtrationfiltered

ORD record

ord-d9d347d9e4334f0998811520a37cfae4

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709468B2