1-Hydroxybenzotriazole → HCID 55556362, compound

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	5-Chloro-1H-indole-2-carboxylic acid	HCID 82693	—
Reactant	tert-Butyl piperazine-1-carboxylate	HCID 143452	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 55556362	HCID 55556362	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

A mixture of 5-chloroindole-2-carboxylic acid (10 g), tert-butyl 1-piperazinecarboxylate (10.5 g) and 4-dimethylaminopyridine (6.3 g) in CH2Cl2 (200 mL) was treated with a catalytic amount of HOBT (0.2 g). The resulting mixture was cooled to 0° C., and EDCl (10.8 g) was added. The reaction was then slowly warmed to ambient temperature and stirred for 24 h then concentrated under reduced pressure. Water was added to the resulting residue. The product precipitated and was washed with water (2×50 mL) and Et2O (30 mL). The resulting solid was dried under reduced pressure to yield (18.2 g). MS (electrospray): exact mass calculated for C18H22ClN3O3, 363.13; m/z found, 362.3 [M−H]−.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06803362B2
Source dataset	uspto-grants-2004_10
ORD ID	ord-53a8ec08d7e64fd1990aaa072f70986a
Source note	uspto-grants-2004_10