Triethylamine → N-(3-Chloropropyl)-1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazol-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
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	1-Propanamine, 3-chloro-, hydrochloride	HCID 11469095	—
Reactant	1-Methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic Acid	HCID 59421802	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(3-Chloropropyl)-1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazol-2-carboxamide	HCID 59421821	—

Reaction Steps

140 mg (0.36 mmol) of 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic acid (Example 29A) are dissolved in 8 ml of DMF and, after addition of 204 mg (0.54 mmol) of HATU and 66 mg (0.54 mmol) of DMAP, stirred at room temperature for 15 minutes. Then a solution of 93 mg (0.72 mmol) of 3-chloropropan-1-amine hydrochloride and 80 mg (0.79 mmol) of triethylamine in 1 ml of DMF is added dropwise, and the reaction mixture is stirred overnight. The reaction mixture is purified by preparative HPLC. The product-containing fractions are evaporated in vacuo.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07767704B2
Source dataset	uspto-grants-2010_08
ORD ID	ord-3a64e892f1424da095ebd32ff4b7a49d
Source note	uspto-grants-2010_08