Diisopropylethylamine → HCID 47017927, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	HOAt	HCID 181649	—
Reactant	5-(Furan-2-yl)-1,3,4-oxadiazol-2-amine	HCID 202185	—
Reactant	5-Phenyl-2-(piperidin-1-yl)-[1,3]thiazolo[4,5-b]pyridine-7-carboxylic acid	HCID 2560413	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 47017927	HCID 47017927	24%

Reaction Steps

2-Amino-5-(2-furyl)-1,3,4-oxadiazole (76 mg, 0.50 mmol), HOAt (68 mg, 0.50 mmol), HATU (190 mg, 0.50 mmol), and N,N-diisopropylethylamine (97 μL, 0.56 mmol) were added to a solution of commercially available 5-phenyl-2-piperidino-7-thiazolo[4,5-b]pyridinecarboxylic acid (85 mg, 0.25 mmol) in DMF (1 mL), followed by stirring overnight at room temperature in an argon atmosphere. To the reaction solution were added 2-amino-5-(2-furyl)-1,3,4-oxadiazole (76 mg, 0.50 mmol), HOAt (68 mg, 0.50 mmol), HATU (190 mg, 0.50 mmol), and N,N-diisopropylethylamine (97 μL, 0.56 mmol), and the mixture was stirred at room temperature for further 4 days. Water was added to the reaction solution, and the precipitated crystals were collected by filtration, washed with water, and recrystallized from methanol to obtain the title compound (27 mg, 0.06 mmol) (yield: 240).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08796320B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-50154004bfb748c5905f3c673fa94578
Source note	uspto-grants-2014_08