3-Aminophenol → N-(3-((6-amino-5-(1-(2-fluorobenzyl)-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	1-[(2-fluorophenyl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 86721829	—
Product	N-(3-((6-amino-5-(1-(2-fluorobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide	HCID 86721828	—

Reaction Steps

N-(3-((6-amino-5-(1-(2-fluorobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 1-(2-fluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole, and acryloyl chloride using methods A, C, and F. HPLC: 100%. MS: m/z=431 [M+H]+. 1H-NMR (DMSO-d6) δ 10.21 (s, 1H), 8.12 (s, 1H), 8.01 (s, 1H), 7.73 (s, 1H), 7.50 (s, 1H), 7.40-7.17 (m, 6H), 6.82-6.65 (m, 3H), 6.42 (dd, 1H), 6.25 (d, 1H), 5.77 (d, 1H), 5.43 (s, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09073947B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-3f48d86e65f4493e87a64341d3765a13
Source note	uspto-grants-2015_07