3,4,5-Trimethoxybenzylamine → N-(2-methyl-5-(6-(3,4,5-trimethoxybenzylamino)imidazo[1,2-b]pyridazin-2-yl)phenyl)pivalamide

참여 물질

역할	이름	HCID	투입량
반응물	3,4,5-Trimethoxybenzylamine	HCID 87736	—
반응물	Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane	HCID 11618717	—
반응물	Sodium t-butoxide	HCID 23676156	—
반응물	N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamide	HCID 86667859	—
촉매	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
용매	Toluene	HCID 1140	—
생성물	N-(2-methyl-5-(6-(3,4,5-trimethoxybenzylamino)imidazo[1,2-b]pyridazin-2-yl)phenyl)pivalamide	HCID 67983329	40%

반응 조건

온도	100 °C

반응 단계

A 40-mL vial is charged with N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-phenyl]-2,2-dimethyl-propanamide (1.0285 g, 3 mmol), tert-butyl xphos (0.255 g, 0.6 mmol), sodium tert-butoxide (0.577 g, 6 mmol), and bis(dibenzylideneacetone)palladium(0) (0.172 g, 0.3 mmol) and the vial is purged with N2. Toluene (16 mL) and 3,4,5-trimethoxybenzylamine (1.54 mL, 9 mmol) is added and the mixture heated at 100° C. for 1 hr. The reaction mixture is filtered through celite, washed with 1:1:0.1 CH2Cl2:EtOAc:MeOH and concentrated onto celite, and purified by silica gel chromatography (0-100% 1:1:0.1 CH2Cl2:EtOAc:MeOH) to afford the title compound (0.604 g). LCMS (m/z)=504.6 [M+H]+, tR=2.31 min.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US08871767B2
출처 데이터셋	uspto-grants-2014_10
ORD ID	ord-1907d305fbb24cd69e53c2d20a983f05
출처 메모	uspto-grants-2014_10