Methylamine → HCID 59613078, compound

Temperature

0 °C

To a solution of 2-amino-5-bromonicotinic acid (Combi-Blocks, San Diego, USA, 1.355 mmol) and triethylamine (0.378 ml) in dichloromethane (10 ml) cooled with an ice-bath was added a solution of trichloromethyl chloroformate (Acros, Basel, Switzerland, 0.677 mmol) in dichloromethane (10 ml). After 40 min stirring at 0° C., was added a solution 8 M of methylamine in EtOH (1.7 ml). The RM was stirred for 30 min at rt then was diluted with dichloromethane, washed with saturated aqueous NaHCO3, with brine, dried over Na2SO4, filtered and evaporated. The residue was taken in DMF and purified by preparative HPLC. The fractions containing product were basified with NaHCO3, concentrated and extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as a white solid. (HPLC: tR 1.69 min (Method A); M+H=230, 232 MS-ES)

1. stirringThe RM was stirred for 30 min at rt
2. washwashed with saturated aqueous NaHCO3, with brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. customevaporated
6. custompurified by preparative HPLC
7. additionThe fractions containing product
8. concentrationconcentrated
9. extractionextracted with dichloromethane (2×)
10. washThe combined organic layers were washed with brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. customevaporated
14. customdried under vacuum

ORD record

ord-1cc181faa03340208df00102fdc4e352

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476294B2