(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid → (E)-3-(6-aminopyridin-3-yl)-N-(5-fluoro-1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

Participants

Role	Name	HCID	Charge
Reactant	(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid	HCID 10487224	—
Reactant	5-fluoro-1-methyl-3-(methylaminomethyl)-1H-indole	HCID 22139018	—
Reactant	2,3-dihydro-8-(methylaminomethyl)-1H-3a-azacyclopenta[a]indene	HCID 22139048	—
Reactant	(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride	HCID 66905305	—
Product	(E)-3-(6-aminopyridin-3-yl)-N-(5-fluoro-1-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide	HCID 10337203	41%

Reaction Steps

According to the procedure of Example 24, except substituting 5-fluoro-1-methyl-3-(methylaminomethyl)-1H-indole (0.2 g, 1.04 mmole) for the 2,3-dihydro-8-(methylaminomethyl)-1H-3a-azacyclopenta[a]indene, and substituting (E)-3-(6-amino-pyridin-3-yl)acrylic acid (0.17 g, 1.04 mmole) for the (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride salt, the title compound (0.14 g, 41%) was prepared as an off-white powder: MS (ES) m/e 339 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08153652B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-e32db832e46348f294fdf667a78bf21f
Source note	uspto-grants-2012_04