Reaction #471853

Reaction equation

(E)-N′-hydroxyacetimidamide

DIPEA

4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)nicotinic acid

HATU

NaCl

→

powder

Yield 77.0%

(E)-tert-Butyl 4-((5-((1-aminoethylideneaminooxy)carbonyl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

Yield 77.0%

Solvents

DMF

DMF

Conditions

Workup

1. 1
   workup.STIRRINGThe resulting solution was stirred at r.t. for 12 hr
2. 2
   Otherthe resulting precipitate was collected
3. 3
   WashThe solid was washed with water and n-hexane

Procedure

DIPEA (96 μL, 0.55 mmol) was added to a solution of 4-((1-(tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)nicotinic acid (Synthesis 75-A) (50 mg, 0.11 mmol), HATU (54 mg, 0.14 mmol) in DMF (6 mL) under argon. The reaction mixture was stirred for 15 min at r.t. and (E)-N′-hydroxyacetimidamide (25 mg, 0.34 mmol) in DMF (0.5 mL) was added. The resulting solution was stirred at r.t. for 12 hr. Aqueous NaCl solution (15 mL) was added and the resulting precipitate was collected. The solid was washed with water and n-hexane to give a yellow powder (43 mg, 77%).

Source