Reaktion #798698

Reaktionsgleichung

methyl 6-chloro-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate

DIPEA

tert-butyl (1S,2R)-2-aminocyclohexylcarbamate

→

title compound

Ausbeute 19.1%

Methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate

Ausbeute 19.1%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeafter which the solvent was removed
2. 2
   workup.ADDITIONthe resulting crude material was diluted in MeOH (5.0 mL)
3. 3
   Sonstigepurified via reverse phase preparative HPLC
4. 4
   SonstigeThe collected fractions were collected
5. 5
   SonstigeACN was removed via rotary evaporation
6. 6
   Waschenwashed with EtOAc (2×200 mL)
7. 7
   Trocknendried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   SonstigeThe organic phase was stripped to dryness via rotary evaporation

Vorschrift

To a solution of methyl 6-chloro-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate (201 mg, 0.691 mmol) in DMF (1 mL) was added DIPEA (0.242 mL, 1.383 mmol) and tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (237 mg, 1.106 mmol). The reaction mixture was stirred at 100° C. overnight, after which the solvent was removed, and the resulting crude material was diluted in MeOH (5.0 mL) and purified via reverse phase preparative HPLC. The collected fractions were collected and ACN was removed via rotary evaporation. The resulting aq solution was neutralized with saturated aq NaHCO3 and washed with EtOAc (2×200 mL), dried over Na2SO4, and filtered. The organic phase was stripped to dryness via rotary evaporation to yield the title compound (62 mg, 19%). [M+H] calc'd for C24H32N6O4, 469. found, 469.

Quelle