Potassium Phosphate, Tribasic → HCID 89525197, compound

HRID 1465741Notes

Reaction equation

HRID 1465741 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[CH:3]=1.[O:13]=[C:14]1[NH:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.CNC1CCCCC1NC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CCOC(C)=O.[Cu]I.O1CCOCC1>[Br:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([N:19]1[CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:15][C:14]1=[O:13])[CH:11]=[CH:10]2

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 6405912,6-DibromonaphthaleneHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 89525197HCID 89525197, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a microwave tube charged with a stir bar was added 2,6-dibromonaphthalene (710 mg, 2.5 mmol), tert-butyl 3-oxopiperazine-1-carboxylate (250 mg, 1.2 mmol), copper(I) iodide (48 mg, 0.25 mmol), N,N′-dimethylcyclohexane-1,2-diamine (71 mg, 0.50 mmol), K3PO4 (530 mg, 2.5 mmol), and dioxane (10 mL). The mixture was heated to 150° C. in a microwave reactor for 1 hour. The reaction was diluted with EtOAc, adsorbed onto silica gel, and purified by MPLC (silica gel, EtOAc-Hexanes) to afford the title compound. LC-MS (IE, m/z): 407 [M+1]+.

Workup

  1. additionTo a microwave tube charged with a stir bar
  2. custompurified by MPLC (silica gel, EtOAc-Hexanes)

Sources & evidence

ORD record
ord-00560ec4cfeb46d6b7f7d49a038e2542
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

Loading…