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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 72512Generated: October 30, 2026

Triethylamine → HCID 67958748, compound

https://huagongshe.com/reaction/72512

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
Reactant1-Hydroxybenzotriazole hydrateHCID 2796029—
ReactantMethyl 4-(1-aminocyclopropyl)benzoate hydrochlorideHCID 66824369—
Reactant5-Chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1-yl)nicotinic acidHCID 67958080—
SolventDimethylformamideHCID 6228—
ProductHCID 67958748HCID 67958748173.5%

Reaction Steps

A mixture of 5-chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1-yl)nicotinic acid (D118) (40 mg, 0.118 mmol), 1-Hydroxybenzotriazole hydrate (18 mg, 0.118 mmol) and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (34 mg, 0.177 mmol) in dimethylformamide (5 ml) was stirred 10 min at room temperature. A solution of methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (D7) (32.2 mg, 0.141 mmol) and triethylamine (0.02 ml, 0.141 mmol) in dry dimethylformamide (2 ml) was added and the mixture was stirred 24 h at room temperature. After solvent evaporation, water (10 ml) was added and the formed precipitate was filtered off and purified by Biotage SNAP-Si (10 g) cartridge eluting with a mixture dichloromethane/methanol from 100/0 to 80/20. Collected fractions, after solvent evaporation afforded the title compound (D169) (105 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08828987B2
Source datasetuspto-grants-2014_09
ORD IDord-f9fd8496b8c24567963244c5777053ad
Source noteuspto-grants-2014_09