Triethylamine → N-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(phenylsulfonylmethyl)cyclohexyl)-3-(pyridin-3-yl)propanamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3-(Pyridin-3-yl)propanoic acid	HCID 259624	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	(1R,3R,4S*)-N1-isopropyl-N1-methyl-3-(phenylsulfonylmethyl)cyclohexane-1,4-diamine	HCID 68468828	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(phenylsulfonylmethyl)cyclohexyl)-3-(pyridin-3-yl)propanamide	HCID 11431032	66%

Reaction Steps

A solution of (1R,3R,4S)-N1-isopropyl-N1-methyl-3-(phenylsulfonylmethyl)-cyclohexane-1,4-diamine (see 30b) (50 mg, 0.154 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (32 mg, 0.166 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (22 mg, 0.166 mmol), Et3N (17 mg, 0.166 mmol) and 3-(pyridin-3-yl)propanoic acid (26 mg, 0.166 mmol) in CH2Cl2 (5 mL) was stirred overnight at room temperature. The mixture was dilute with CH2Cl2 (20 mL) and washed with water, brine and evaporated. The residue was chromatographed on silica gel (4-6% NH4OH/MeOH/CH2Cl2) to give the product (45 mg, 66%). MS found: (M+1)+: 458.53.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07696205B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-bdf2315617d841ad831f62ca574684f4
Source note	uspto-grants-2010_04