1-Hydroxybenzotriazole → (2-{3-Chloro-5-[(2-cyano-ethyl)-cyclopentyl-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	3-(Cyclopentylamino)propionitrile	HCID 2758002	—
Reactant	Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-	HCID 18348849	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(2-{3-Chloro-5-[(2-cyano-ethyl)-cyclopentyl-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester	HCID 54100150	146.2%

Reaction Steps

To a stirred solution of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.100 g), TBTU (0.080 g) and HOBt (0.034 g) in DMF (3 ml) was added DIPEA (0.087 ml) followed by 3-(cyclopentylamino)propionitrile (0.035 g) after 15 min. The reaction mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure. The residue was washed with water and extracted with ethyl acetate. The organic layer was dried with brine and MgSO4, filtered and concentrated to give the title compound (0.190 g) as a brown oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06326386B1
Source dataset	uspto-grants-2001_12
ORD ID	ord-95e84b4d8cb940579398e3e7e0895bb2
Source note	uspto-grants-2001_12