Cyclopropylamine → 3-Bromo-4-chloro-N-cyclopropylbenzamide

Participants

Role	Name	HCID	Charge
Reactant	Cyclopropylamine	HCID 69828	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-Bromo-4-chlorobenzoic acid	HCID 2735544	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Methanol	HCID 887	—
Solvent	Dimethylformamide	HCID 6228	—
Product	3-Bromo-4-chloro-N-cyclopropylbenzamide	HCID 18457794	—

Reaction Steps

To a solution of 3-bromo-4-chlorobenzoic acid (120 mg) in DMF (1 ml) was added a solution of HATU (192 mg) in DMF (1 ml) and a solution of HOBT (69 mg) in DMF (1 ml). To this mixture was added cyclopropylamine (0.04 ml) and DIPEA (0.27 ml). The reaction was stirred at room temperature for 18 hours, before diluting with methanol (5 ml) and filtration through a SPE cartridge (SCX, 2 g). The filtrate was applied to a SPE cartridge (Aminopropyl, 10 g) and washed through with methanol (10 ml). The combined filtrate and washings were reduced to dryness under vacuum to give 3-bromo-4-chloro-N-cyclopropylbenzamide.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07208629B2
Source dataset	uspto-grants-2007_04
ORD ID	ord-ee08f686d32f4a7691d59f0f5a009837
Source note	uspto-grants-2007_04