Bromide ion → (R)-4-(4-(1H-imidazol-1-yl)phenyl)-3-amino-1-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)butan-1-one

Participants

Role	Name	HCID	Charge
Reactant	Bromide ion	HCID 259	—
Reactant	Imidazole	HCID 795	—
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	tert-butyl (R)-1-(4-bromophenyl)-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate	HCID 66791560	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(R)-4-(4-(1H-imidazol-1-yl)phenyl)-3-amino-1-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)butan-1-one	HCID 66786089	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

A suspension of bromide, tert-butyl (R)-1-(4-bromophenyl)-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate (prepared from the procedure of Example 6, Step A) (45 mg, 0.088 mmol), imidazole (11 mg, 2 eq), CuI (3.3 mg, 20% mol), N,N′-dimethylethylenediamine (3.1 mg, 40% mol), potassium phosphate (K3PO4) (37.4 mg, 2 eq) in 2 mL dioxane was heated at 110° C. for 27 hrs. The mixture was filtered; the filtrate was washed with EtOAc and concentrated to give a greenish oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08138168B1
Source dataset	uspto-grants-2012_03
ORD ID	ord-a8984d92d1584b3895b1a374b590ae64
Source note	uspto-grants-2012_03