Ammonia → HCID 69203453, compound

3,11-Diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-11-carbaldehyde (75 mg, 0.4 mmol) was stirred in 1M BH3.THF complex (3 mL) at reflux for 18 h at which time additional 1M BH3.THF complex was introduced (3 mL). Heating was continued for 3 days at which time the mixture was cooled and treated with 1N HCl (5 mL) and conc. HCl (1 mL) and the resulting mixture refluxed for 24 h. The mixture was cooled, treated with solid NaOH to achieve pH 10 and extracted with EtOAc (4×10 mL). The organic layer was washed with saturated aqueous NaCl solution (30 mL), dried over Na2SO4, filtered and concentrated to give 48 mg. This material was dissolved in MeOH and treated with 1 mL 3N HCl/EtOAc solution, stirred and concentrated. After recrystallization from MeOH/Et2O, product was filtered and dried to give white solids (49 mg 59%). Mp 260–266° C.; (TLC ˜0.2% NH3/5% CH3OH/dichloromethane Rf 0.33); 1H NMR (400 MHz, CD3OD) δ 8.73 (d, J=5.0 Hz, 1H), 8.42 (d, J=8.1 Hz, 1H), 7.95 (m, 1H), 3.78–3.15 (m, 7H), 2.82 (s, 3H), 2.74 (br s, 1H), 2.28 (d, J=13.6 Hz, 1H), 2.09 (d, J=13.6 Hz, 1H); GCMS m/z 188 (M+).

1. temperatureat reflux for 18 h at which time additional 1M BH3.THF complex
2. additionwas introduced (3 mL)
3. temperatureHeating
4. temperaturethe mixture was cooled
5. temperaturethe resulting mixture refluxed for 24 h
6. temperatureThe mixture was cooled
7. extractionextracted with EtOAc (4×10 mL)
8. washThe organic layer was washed with saturated aqueous NaCl solution (30 mL)
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customto give 48 mg
13. concentrationconcentrated
14. customAfter recrystallization from MeOH/Et2O, product
15. filtrationwas filtered
16. customdried
17. customto give white solids (49 mg 59%)

ORD record

ord-2fec104ff5044624864c065bf6f82284

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456177B2