Methyl 4-prop-2-ynylcyclohexanecarboxylate → Apadenoson

Participants

Role	Name	HCID	Charge
Reactant	Methyl 4-prop-2-ynylcyclohexanecarboxylate	HCID 10749876	—
Reactant	(2s,3s,4r,5r)-5-(6-Amino-2-Iodo-9h-Purin-9-Yl)-N-Ethyl-3,4-Dihydroxytetrahydrofuran-2-Carboxamide	HCID 11697766	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Acetonitrile	HCID 6342	—
Product	Apadenoson	HCID 9805430	24%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a degassed solution of 25 mg (0.063 mmol) of [(2S,3S,4R,5R)-5-(6-amino-2-iodopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-N-ethylcarboxamide (6.9), 16.9 mg (0.094 mmol) (5.5), and 0.75 mg CuI in 5 mL each of TEA and acetonitrile was added 15 mg of Pd(PPh3)4. The solution was stirred for 24 hours at 70° C. after which time the solution was filtered through celite and chromatographed on silica gel with MeOH-CHCl3 (5:95) to give DWH-146e (24%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06322771B1
Source dataset	uspto-grants-2001_11
ORD ID	ord-cab41cf2de6b4f069c7845e0dd99bee8
Source note	uspto-grants-2001_11