Diisopropylethylamine → HCID 44199820, compound

https://huagongshe.com/reaction/2061179

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-Oxocyclopentanecarboxylic acid	HCID 227798	—
Reactant	Sodium borohydride	HCID 4311764	—
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 178422078	HCID 178422078	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 44199820	HCID 44199820	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

3-Oxocyclopentanecarboxylic acid (16.6 mg, 0.12 mmol), HATU (50 mg, 0.12 mmol), and DIPEA (0.023 mL, 0.12 mmol) were stirred in dry DMF (3 mL) for 1 h before 17 (40 mg, 0.118 mmol) was added at rt. The stirring was continued for 1 h before it was heated at 100° C. for 5 h. After cooling NaBH4 (20 mg) was added and stirred for 5 h at rt. After filtration, the mixture was purified by preparative LC/MS to give 3-(5-(5-(3-hydroxycyclopentyl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-di methyl-1,6-naphthyridin-2(1H)-one (A73) as a solid. MS m/z 431.5, 432.6 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08278452B2
Source dataset	uspto-grants-2012_10
ORD ID	ord-22c937669cc3412c986af238feec4277
Source note	uspto-grants-2012_10