Diisopropylethylamine → (1R,2R)-N-(1-cyanocyclopropyl)-2-(6-(2-(dimethylamino)ethoxy)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-2-carbonyl)cyclohexanecarboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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	trans-Cyclohexane-1,2-dicarboxylic anhydride	HCID 10942665	—
Reactant	1-Amino-1-cyclopropanecarbonitrile hydrochloride	HCID 14586363	—
Reactant	N,N-dimethyl-2-(2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yloxy)ethanamine	HCID 57541284	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(1R,2R)-N-(1-cyanocyclopropyl)-2-(6-(2-(dimethylamino)ethoxy)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-2-carbonyl)cyclohexanecarboxamide	HCID 25112828	23%

Reaction Steps

(3aR,7aR)-hexahydroisobenzofuran-1,3-dione (125 mg, 0.81 mmol) was added to N,N-dimethyl-2-(2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yloxy)ethanamine (210 mg, 0.81 mmol) in DMF (10 ml) at room temperature under air. The resulting solution was stirred at room temperature for 2 hours. N,N-Diisopropylethylamine (0.535 ml, 3.24 mmol), HATU (462 mg, 1.21 mmol) and 1-amino-1-cyclopropanecarbonitrile HCL (144 mg, 1.21 mmol) were then added to the mixture. The resulting solution was stirred at room temperature for 20 hours. The crude product was purified by preparative HPLC (0.1% NH3, CH3CN/H2O gradient) as eluents to afford as a brown gum (89 mg, 23%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08008279B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-ab4c8d1c547e4a7cb2168ab6c119c52e
Source note	uspto-grants-2011_08