1,2-Diaminocyclohexane → HCID 58998455, compound

HRID 1593083Notes

Reaction equation

HRID 1593083 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[NH:13][CH3:14].I[C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.NC1CCCCC1N.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CC#N.O.[Cu]I>[NH2:20][C:19]1[CH:21]=[CH:22][C:16]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:2]([F:1])=[C:3]([NH:13][CH3:14])[CH:4]=3)[C:9]2=[O:12])=[CH:17][CH:18]=1

Participants

9

Reactant 4

HCID 46101,2-DiaminocyclohexaneHCID 108934-IodoanilineHCID 62657Potassium Phosphate, TribasicHCID 58998399HCID 58998399, compound

Product 1

HCID 58998455HCID 58998455, compoundYield 60.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 7-fluoro-6-(methylamino)-3,4-dihydroisoquinolin-1(2H)-one (70 mg, 0.36 mmol), 4-iodoaniline (119 mg, 0.543 mmol), CuI (27 mg, 0.14 mmol), 1,2-diaminocyclohexane (44 uL, 0.36 mmol) and K3PO4 (153 mg, 0.722 mmol) in dioxane (1.5 mL) was heated at 110° C. overnight, then diluted with CH3CN (5 mL) and H2O (5 mL) and filtered. The filtrate was purified by RP-HPLC to give the noted intermediate compound as a solid (62 mg). ES-MS (M+H)+=286.

Workup

  1. filtrationfiltered
  2. customThe filtrate was purified by RP-HPLC

Sources & evidence

ORD record
ord-f6a2b0c692704ddb955229a122b58355
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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