Sodium Chloride → [(E)-1-aminoethylideneamino] 6-[(5-cyanopyrazin-2-yl)amino]-4-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methylamino]pyridine-3-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Chloride	HCID 5234	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	22059-22-9	HCID 5360664	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	4-((1-(Tert-butoxycarbonyl)piperidin-4-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)nicotinic acid	HCID 59613465	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[(E)-1-aminoethylideneamino] 6-[(5-cyanopyrazin-2-yl)amino]-4-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methylamino]pyridine-3-carboxylate	HCID 59613429	77%

Reaction Steps

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%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08367658B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-3b5f3b6745004473a25c317baf6eb4fe
Source note	uspto-grants-2013_02