Triethylamine → 2-Methyl-n-(6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-nicotinamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Methylnicotinic acid	HCID 643373	—
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	8-Amino-2-phenyl-1,5-dihydro-[1,2]diazepino[4,5,6-cd]indol-6-one	HCID 135774079	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-Methyl-n-(6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-nicotinamide	HCID 135434039	33.3%

Reaction Steps

Preparation of example 14 from the title compound of Example 7 (15 mg, 0.054 mmol), 2-methyl-nicotinic acid (9 mg, 0.062 mmol), triethylamine (0.030 mL, 0.22 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (25 mg, 0.065 mmol) in N,N-dimethylformamide (1.0 mL) was carried out analogously to Example 11. Silica gel chromatography (ethyl acetate), also in an analogous manner, followed by diethyl ether trituration afforded the title compound (7 mg, 0.018 mmol) as a yellow powder in 33% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06967198B2
Source dataset	uspto-grants-2005_11
ORD ID	ord-2fed66ae0aac4b99905f914a194bf1b4
Source note	uspto-grants-2005_11