Dimethylformamide → 6-azido-N,N-dimethylnicotinamide

In a 500 mL round-bottomed flask, 6-chloro-N,N-dimethylnicotinamide (8.15 g, 44.1 mmol) was combined with DMF (50.0 ml) to give a brown solution. Sodium azide (3.44 g, 53.0 mmol) was added and the reaction mixture was heated to 120° C. and stirred for 60 h. The reaction mixture was diluted with 100 mL H2O and extracted with EtOAc (2×200 mL). The organic layers were combined, washed with H2O (1×50 mL), sat NaCl (1×100 mL), dried over Na2SO4 and concentrated in vacuo to a yellow oil. MeOH was added and the entire mixture solidified upon concentration. The crude product was dried under vacuum overnight. The pasty solid was recrystallized from EtOAc/Hex. The solid was filtered and washed with a minimal amount of hexane. The white powder was dried under vacuum at 45° C. for 3 hrs to give 2.23 g (26%) of the title compound. 1H NMR (300 MHz, CHLOROFORM-d) δ: 8.95 (s, 1H), 8.09 (d, J=9.1 Hz, 1H), 7.75 (dd, J=9.1, 1.5 Hz, 1H), 3.15 (br. s., 6H).

1. customto give a brown solution
2. extractionextracted with EtOAc (2×200 mL)
3. washwashed with H2O (1×50 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo to a yellow oil
6. additionMeOH was added
7. concentrationthe entire mixture solidified upon concentration
8. dry with materialThe crude product was dried under vacuum overnight
9. customThe pasty solid was recrystallized from EtOAc/Hex
10. filtrationThe solid was filtered
11. washwashed with a minimal amount of hexane
12. customThe white powder was dried under vacuum at 45° C. for 3 hrs

ORD-Eintrag

ord-9131652ef5ec4e14a71ca4c15285167f

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08481540B2