Reaktion #1018384

Reaktionsgleichung

(R)—N-(2-amino-6-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)-1-(pyridin-3-yl)cyclopropanecarboxamide

sodium methoxide

→

(R)-(1-(2-(1-(pyridin-3-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

Ausbeute 21.3%

Lösungsmittel

isobutanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated under a nitrogen stream
2. 2
   SonstigeThe residue was partitioned between water (0.5 mL) and ethyl acetate (1.5 mL×3)
3. 3
   TrocknenThe combined organics were dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified via HPLC

Vorschrift

To a solution of (R)—N-(2-amino-6-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)-1-(pyridin-3-yl)cyclopropanecarboxamide (35 mg, 0.081 mmol) in isobutanol (500 μL) was added sodium methoxide (18 mg, 0.335 mmol) in methanol (250 μL). The reaction mixture was shaken 110° C. for 18 h. The solvent was evaporated under a nitrogen stream. The residue was partitioned between water (0.5 mL) and ethyl acetate (1.5 mL×3). The combined organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified via HPLC to afford (R)-(1-(2-(1-(pyridin-3-yl)cyclopropyl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (7.2 mg). MS (ESI+) (M+H) 417.3; HPLC retention time 1.59 min (Method A).

Quelle