4-Methoxybenzylamine → 2-{4-[4-(4-Methoxy-benzylamino)-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl]-phenyl}-2-methyl-propionitrile

https://huagongshe.com/reaction/1971237

Participants

Role	Name	HCID	Charge
Reactant	4-Methoxybenzylamine	HCID 75452	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	2-[4-(4-Chloro-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-2-methyl-propionitrile	HCID 53630358	—
Catalyst	[(1R,4S)-2-Bicyclo[2.2.1]heptanyl]-[(1S,4R)-2-bicyclo[2.2.1]heptanyl]phosphane;chloropalladium(1+);N,N-dimethyl-2-phenylaniline	HCID 11272965	—
Solvent	Toluene	HCID 1140	—
Product	2-{4-[4-(4-Methoxy-benzylamino)-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl]-phenyl}-2-methyl-propionitrile	HCID 53630357	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

100 mg (0.198 mmol) of 2-[4-(4-chloro-3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-2-methyl-propionitrile (Example 109b), 27 mg (0.278 mmol) sodium tert-butanolate, 11 mg (0.02 mmol) SK-CC01-A catalyst and 33 mg (0.238 mmol) 4-methoxybenzylamine in 0.4 ml degassed toluene under argon are heated at 100° C. for 22 h. The reaction mixture is quenched with sat. aqueous NaHCO3 and extracted with CH2Cl2 (2×). The organic layers are washed with sat. aqueous NaHCO3, dried over Na2SO4, filtered and evaporated to provide the title compound as a crude brown solid. ES-MS: 605 (M+H)+; analytical HPLC: tret=3.29 minutes (Grad 1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08431592B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-ccb2058bba0d498c889ba80d45a7f620
Source note	uspto-grants-2013_04