2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5-pyrimidinediamine → N5-[1-(2,2-Difluoroethyl)piperidin-4-yl]-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5-diamine

Participants

Role	Name	HCID	Charge
Reactant	2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5-pyrimidinediamine	HCID 21934817	—
Reactant	1-(2,2-Difluoroethyl)piperidin-4-one	HCID 47002711	—
Product	N5-[1-(2,2-Difluoroethyl)piperidin-4-yl]-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5-diamine	HCID 86720048	—

Reaction Steps

200 mg (0.596 mmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5-diamine (synthesis described in US2004/67937; Example V) were reacted in analogy to the method in example 88A with 1-(2,2-difluoroethyl)piperidin-4-one. After purification by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient), this gave 219 mg of the title compound (76% of theory).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09096592B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-8574c7b2925840848f9d7891311c1819
Source note	uspto-grants-2015_08