Triethylamine → tert-Butyl (1R)-1-cyclohexyl-2-oxo-2-[(6-oxo-2-phenyl-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)amino]ethylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	(2R)-2-(((tert-butoxy)carbonyl)amino)-2-cyclohexylacetic acid	HCID 7014890	—
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	Hexane	HCID 8058	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	tert-Butyl (1R)-1-cyclohexyl-2-oxo-2-[(6-oxo-2-phenyl-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)amino]ethylcarbamate	HCID 136181616	70%

Reaction Steps

Preparation of example 59 from the title compound of Example 7 (70 mg, 0.25 mmol), (2R)-[(tert-butoxycarbonyl)amino](cyclohexyl)ethanoic acid (98 mg, 0.38 mmol), triethylamine (0.139 mL, 1.0 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (144 mg, 0.38 mmol) in N,N-dimethylformamide (2.0 mL) was carried out analogously to Example 11 except that after 24 hours additional (2R)-[(tert-butoxycarbonyl)amino](cyclohexyl)ethanoic acid (32 mg, 0.13 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (48 mg, 0.13 mmol) were added to drive the reaction to completion. Silica gel chromatography (1:1 ethyl acetate:hexane), also in an analogous manner, followed by diethyl ether trituration afforded the title compound (90 mg, 0.17 mmol) as a yellow powder in 70% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07462713B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-8a1dd59be96f45c39873bdb4b6d82ea9
Source note	uspto-grants-2008_12