Triethylamine → (3S)-N-{1-[(3-Fluoro-5-phenyl-1-benzothiophen-2-yl)carbonyl]azetidin-3-yl}-1-(phenylcarbonyl)pyrrolidin-3-amine

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3-Fluoro-5-phenyl-benzo[b]thiophene-2-carbonyl chloride	HCID 59625725	—
Reactant	(S)-(3-(Azetidin-3-ylamino)pyrrolidin-1-yl)(phenyl)methanone	HCID 67288563	—
Solvent	Dichloromethane	HCID 6344	—
Product	(3S)-N-{1-[(3-Fluoro-5-phenyl-1-benzothiophen-2-yl)carbonyl]azetidin-3-yl}-1-(phenylcarbonyl)pyrrolidin-3-amine	HCID 67287028	26.7%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a solution of compound 5e (42.7 mg, 0.131 mmol) and Et3N (0.07 mL, 0.5 mmol) in CH2Cl2 (2 mL) at 0° C. was slowly added a solution of compound 13e (36.3 mg, 0.125 mmol) in CH2Cl2 (1 mL). The reaction was stirred at 0° C. for 2 h, diluted with CH2Cl2, and washed with aqueous NaHCO3. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography (silica gel, % MeOH/EtOAc) to give compound Cpd 173 (16.7 mg). MS m/z (M+H+) 500.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748417B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-075520bfffc343d8afc855488f3ab042
Source note	uspto-grants-2014_06