Sodium Chloride → N-((6-amino-2-methylpyridin-3-yl)methyl)-1-((2-methylquinolin-6-yl)methyl)-1H-pyrazole-4-carboxamide

Temperatur

50 °C

To a suspension of 1-((2-methylquinolin-6-yl)methyl)-1H-pyrazole-4-carboxylic acid (incl. NaCl) (100 mg, 0.337 mmol), EDC.HCl (84 mg, 0.438 mmol) and HOAt (59.6 mg, 0.438 mmol) in DMF (1 ml) was added N-methylmorpholine (0.185 ml, 1.684 mmol). The reaction mixture was stirred for 1 h at 50° C., then 5-(aminomethyl)-6-methylpyridin-2-amine (70.7 mg, 0.337 mmol) was added. Stirring continued at 50° C. for 18 h. Reaction mixture was diluted with methanol, then applied onto a PL-SO3H cartridge (500 mg/6 ml by VARIAN) to catch the desired amine product, washed the cartridge with DMF, DCM and MeOH to remove all impurities, then the product was released from the cartridge by washing with 2M NH3 in MeOH. The basic filtrate was evaporated to give the crude material, which was treated with 0.2 ml of MeOH and 1 ml of ACN in ultrasonic bath. The precipitate formed was filtered, washed with 1 ml of ACN and dried under high vacuum for 4 days to yield the title compound. HPLC (Method J) Rt=2.373 min, MS (Method V) [M+H]+=387.1.

1. stirringStirring
2. waitcontinued at 50° C. for 18 h
3. customReaction mixture
4. washwashed the cartridge with DMF, DCM and MeOH
5. customto remove all impurities
6. washby washing with 2M NH3 in MeOH
7. customThe basic filtrate was evaporated
8. customto give the crude material, which
9. customThe precipitate formed
10. filtrationwas filtered
11. washwashed with 1 ml of ACN
12. customdried under high vacuum for 4 days

ORD-Eintrag

ord-1eee77baa79a4995a82d67ed559d2e14

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09290485B2