3-Aminophenol → N-(3-((6-amino-5-(1-(3-cyanobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide

Participants

Role	Name	HCID	Charge
Reactant	3-Aminophenol	HCID 11568	—
Reactant	Acryloyl chloride	HCID 13140	—
Reactant	5,6-Dichloro-pyrimidin-4-ylamine	HCID 24219262	—
Reactant	3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)benzonitrile	HCID 71092746	—
Product	N-(3-((6-amino-5-(1-(3-cyanobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide	HCID 86721843	—

Reaction Steps

N-(3-((6-amino-5-(1-(3-cyanobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)benzonitrile, and acryloyl chloride using methods A, C, and F. HPLC: 100%. MS: m/z=438 [M+H]+. 1H-NMR (DMSO-d6) δ 10.20 (s, 1H), 8.18 (s, 1H), 8.00 (s, 1H), 7.79-7.74 (m, 3H), 7.65-7.50 (m, 3H), 7.41 (d, 1H), 7.31 (t, 1H), 6.81 (d, 1H), 6.69 (broad s, 2H), 6.42 (dd, 1H), 6.25 (d, 1H), 5.77 (d, 1H), 5.44 (s, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09073947B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-8ebce4f355e945ef9cdef7c882a70e14
Source note	uspto-grants-2015_07