1-Methylimidazole → Tert-butyl 4-(1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidine-3-carboxamido)benzoate

Participants

Role	Name	HCID	Charge
Reactant	1-Methylimidazole	HCID 1390	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	Benzoic acid, 4-amino-, 1,1-dimethylethyl ester	HCID 233272	—
Reactant	1-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidine-3-carboxylic acid	HCID 86682744	—
Solvent	Dichloromethane	HCID 6344	—
Product	Tert-butyl 4-(1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidine-3-carboxamido)benzoate	HCID 86682745	139.5%

Reaction Steps

A mixture of 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidine-3-carboxylic acid (100 mg, 0.25 mmol), tert-butyl 4-aminobenzoate (49 mg, 0.25 mmol), EDCI (192 mg, 1.0 mmol) and 1-methyl-1H-imidazole (82 mg, 1.0 mmol) in dichloromethane (3 mL) was stirred at room temperature for 16 h. The residue was concentrated to give crude tert-butyl 4-(1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidine-3-carboxamido)benzoate (200 mg, crude) as brown liquid that was used directly without further purification. LC-MS: 574 [M+1]+, tR=1.720 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09169259B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-5a823de7a43646f1b04099e1ed491072
Source note	uspto-grants-2015_10