Methanol → HCID 53475914, compound

Temperature

80 °C

Commercially available (6-chloropyridin-3-yl)methanamine (1 g, 7 mmol) was dissolved in 40 ml of AcOEt and at 0° C. triphosgene (1.93 g, 7 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 10 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (1 g, 6.7 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt 9.5/MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (80 ml) and washed with water (1×40 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 450 mg of a pale yellow solid. Yield=21% 1HNMR (DMSO, 200 MHz) δ 4.32 (2H, d, J=5.8 Hz), 6.62 (1H, d, J=7.2 Hz), 6.85 (3H, m), 7.48 (1H, d, J=8.4 Hz), 7.81 (1H, dd, J=8.2 Hz, J′=2.4 Hz), 8.33 (2H, m), 10.02 (1H, bs), 10.60 (1H, bs); [M+1] 317.8 (C14H12ClN5O2 requires 317.73).

1. additionwas added to the solution
2. customthen evaporated
3. dissolutionthe residue was dissolved in 10 ml of DMF
4. temperaturethe mixture was warmed at 80° C. for 8 hours
5. customThe solvent was evaporated
6. dissolutionthe crude was dissolved in AcOEt (80 ml)
7. washwashed with water (1×40 ml) and brine
8. dry with materialThe organic phase was dried over sodium sulfate
9. concentrationconcentrated under vacuum
10. customThe purification of the crude residue by chromatographic column

ORD record

ord-f8aff1abb19647a4a75905adc835eac2

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216975B2