1,2-Dichloroethane → HCID 86686976, compound

Temperature

60 °C

2-Cyano-5-fluoropyridine (1.00 g, 8.19 mmol) was dissolved in hydrochloric acid (37% aqueous, 1.0 mL) and heated to 60° C. for 18 h and then evaporated in vacuo. The residue was suspended in DMF (40.0 mL) and EDC (1.89 g, 9.83 mmol), HOBt (111 mg, 0.82 mmol), morpholine (787 μL, 9.00 mmol) and triethylamine (1.25 mL, 9.00 mmol) were added and the reaction stirred for 18 h. The reaction was partitioned between water (200 mL) and EtOAc (100 mL), and extracted into EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by FCC, using 0-8% [2M NH3 in MeOH] in DCM, to give the title compound (350 mg), contaminated with a single impurity (˜10% by NMR integration). The product was used in the next step without further purification. LCMS (Method 1): Rt 1.88 min, m/z 211 [MH+].

1. customevaporated in vacuo
2. customThe reaction was partitioned between water (200 mL) and EtOAc (100 mL)
3. extractionextracted into EtOAc (3×)
4. washThe combined organic layers were washed with brine
5. dry with materialdried (MgSO4)
6. customevaporated in vacuo
7. customThe residue was purified by FCC

ORD record

ord-52ce95e9714d4733b374532a3cc291b2

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139584B2