Water → 9-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-3-carboxylic acid pyridin-3-ylamide

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	3-Aminopyridine	HCID 10009	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	9-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-3-carboxylic acid	HCID 58767561	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dimethylformamide	HCID 6228	—
Product	9-Oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-3-carboxylic acid pyridin-3-ylamide	HCID 15604845	20%

Reaction Conditions

Temperature	65 °C

Reaction Steps

To a solution of 9-oxo-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-3-carboxylic acid (983 mg, 4.29 mmol) in anhydrous DMF (5 mL) was added HATU (4.00 g, 10.5 mmol), DMAP (3.00 g, 25.0 mmol) and pyridine-3-ylamine (1.00 g, 10.6 mmol). The reaction was stirred at 65° C. for 36 h. The reaction was poured into water and the resulting precipitate was filtered, washed with water and triturated with cold MeCN to give the title compound (256 mg, 20%) as an analytically pure as a brown powder; ESI-MS m/z 306 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07790712B2
Source dataset	uspto-grants-2010_09
ORD ID	ord-2a40bde6bae84bda81a7ca3945110d31
Source note	uspto-grants-2010_09