1,2-Diaminocyclohexane, trans- → HCID 44183500, compound

https://huagongshe.com/reaction/1966398

Participants

Role	Name	HCID	Charge
Reactant	1,2-Diaminocyclohexane, trans-	HCID 43806	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1,1'-[Sulfonylbis(methylene)]bis(4-bromobenzene)	HCID 267419	—
Reactant	(4-Isopropoxy-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-2-yl)-amine	HCID 68639256	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 44183500	HCID 44183500	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

In a sealed tube, (4-Isopropoxy-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-2-yl)-amine (350 mg, 1.17 mmol), 4-bromophenylmethylsulfone (552 mg, 2.35 mmol), CuI (68.4 mg, 0.352 mmol), and K3PO4 (763 mg, 3.52 mmol) are suspended in 1,4-dioxane (10 mL). Then, trans-1,2-diaminocyclohexane (42.7 μL, 0.352 mmol) is added at rt. The reaction vial is flushed with Ar and the mixture is heated to 110° C. for 6 h. After cooling to rt, the reaction mixture is diluted with EtOAc and the organic layer is washed with saturated aqueous NaCl solution (3×). The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue is purified by reverse phase prep-HPLC (Waters) to afford the title compound (3) as an off-white solid. HPLC: tR=1.67 min (Method A); MS-ES: (M+H)+=423.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08420657B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-2d5d7f9b586a4754b12224745d4a990d
Source note	uspto-grants-2013_04