Triethylamine → HCID 67397401, compound

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Benzo(b)thiophene-2-carboxylic acid	HCID 95864	—
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	HCID 67397013	HCID 67397013	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 67397401	HCID 67397401	—

Reaction Steps

To a 2-dram vial was added triethylamine (0.156 mL, 1.12 mmol), HATU (0.106 g, 0.28 mmol), 1-benzothiophene-2-carboxylic acid (0.050 g, 0.28 mmol), and DCM (3 mL). The solution was stirred at rt for 30 min, then transferred to another 2-dram vial containing solid (R)-tert-butyl 5-(1-aminoethyl)thiophene-2-carboxylate hydrochloride. The mixture was stirred at rt for 16 h. To the reaction was then added DCM (3 mL) and water (1 mL). After separation, the aqueous layer was extracted with DCM (2×3 mL). The combined organic phases were evaporated to dryness to give (R)-tert-butyl 5-(1-(benzothiophene-2-carboxamido)ethyl)thiophene-2-carboxylate as a brown solid. LC-MS: (FA) ES+ 388.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09227951B2
Source dataset	uspto-grants-2016_01
ORD ID	ord-2548cd4db9a44b65af484b2417b6e4f7
Source note	uspto-grants-2016_01