Cesium carbonate → HCID 58504634, compound

Into a 40 mL vial was added 4-{2-amino-6-[(3R)-3-amino-1-piperidinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (100 mg, 0.260 mmol) followed by THF (3 mL) and saturated NaHCO3 (1.5 mL), and the resulting mixture was stirred for 5 minutes. Then 2-chloroethyl chloridocarbonate (0.032 mL, 0.311 mmol) was added, and the reaction mixture was capped and stirred at room temperature overnight. The reaction was then diluted with 5 mL of water and extracted with EtOAc (3×10 mL). The organic was combined and washed with saturated NaCl, dried over MgSO4, filtered and concentrated. The resulting light yellow solid (114 mg) was dissolved in DMF (3.00 mL), and then Cs2CO3 (127 mg, 0.389 mmol) was added, and the reaction was stirred at room temperature overnight. The reaction was incomplete. Additional 0.5 equiv of Cs2CO3 was added, and the reaction mixture was continue to stir at room temperature. After 5 hours, the reaction was completed, and then it was diluted with 10 mL water, and extracted with EtOAc (3×10 mL). The organics were combined, washed with saturated NaCl, dried over MgSO4, filtered and concentrated to afford the crude title compound (83 mg). LC-MS (ES) m/z=383 [M+H]+.

1. customthe reaction mixture was capped
2. stirringstirred at room temperature overnight
3. extractionextracted with EtOAc (3×10 mL)
4. washwashed with saturated NaCl
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutionThe resulting light yellow solid (114 mg) was dissolved in DMF (3.00 mL)
9. stirringthe reaction was stirred at room temperature overnight
10. stirringto stir at room temperature
11. waitAfter 5 hours
12. extractionextracted with EtOAc (3×10 mL)
13. washwashed with saturated NaCl
14. dry with materialdried over MgSO4
15. filtrationfiltered
16. concentrationconcentrated

ORD record

ord-4cb4f5cd522742cca05ba1cb68cc0452

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697685B2