Urea → 1-(4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)-3-(4-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)urea

Participants

Role	Name	HCID	Charge
Reactant	Urea	HCID 1176	—
Reactant	Aniline	HCID 6115	—
Reactant	N-(2-Dimethylaminoethyl)-N-methylbenzene-1,4-diamine	HCID 21873395	—
Reactant	ethyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-ethylureido)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate	HCID 25262323	—
Product	1-(4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)-3-(4-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)urea	HCID 57424687	—

Reaction Steps

A urea formation procedure similar to that used for the synthesis of ethyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-ethylureido)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate is used, utilizing N1-(2-(dimethylamino)ethyl)-N1-methylbenzene-1,4-diamine as the aniline component. (40%, MS=570.5 (M+H))

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08129371B2
Source dataset	uspto-grants-2012_03
ORD ID	ord-c2632c849d5b432b85d1a902b2a990cf
Source note	uspto-grants-2012_03