L-Hydroxyproline → HCID 21822966, compound

Participants

Role	Name	HCID	Charge
Reactant	L-Hydroxyproline	HCID 5810	—
Reactant	Isopropylamine	HCID 6363	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	HCID 57924514	HCID 57924514	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	HCID 21822966	HCID 21822966	142%

Reaction Conditions

Temperature	70 °C

Reaction Steps

A sealed tube was charged with methyl 3-bromopyridin-4-ylcarbamate (1.76 g, 7.6 mmol.), CuI (290 mg, 1.52 mmol.), trans-4-hydroxy-L-proline (400 mg, 3.04 mmol.) and K3PO4 (3.2 g, 15.2 mmol.), evacuated and backfilled with argon. Isopropylamine (674 mg, 11.4 mmol.) and DMSO (15 mL) were added successively. The reaction mixture was stirred at 70° C. for 12 h and then at 130° C. for 12 h. The reaction mixture filtered and the filtrate was concentrated and purified by prep-HPLC to afford 3-isopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one (765 mg, 57%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08048862B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-67c6249ebc774af9a86179249435ddf8
Source note	uspto-grants-2011_11