Cesium carbonate → HCID 86685990, compound

HRID 2277695Notes

Reaction equation

HRID 2277695 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.Br[C:14]1[CH:15]=[C:16]([CH:20]([NH:22][CH3:23])[CH3:21])[CH:17]=[N:18][CH:19]=1.[C@H]1(N)CCCC[C@@H]1N.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.[Cu]I.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:14]1[CH:19]=[N:18][CH:17]=[C:16]([CH:20]([NH:22][CH3:23])[CH3:21])[CH:15]=1)[CH2:6][CH2:5]2

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 4793071,2-Diaminocyclohexane, (+)-HCID 193756376-Chloro-3,4-dihydroisoquinolin-1(2H)-oneHCID 80202111HCID 80202111, compound

Product 1

HCID 86685990HCID 86685990, compoundYield 26%

Reagents, catalysts & solvents 3

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

Procedure

6-Chloro-3,4-dihydro-2H-isoquinolin-1-one (intermediate A-2) (36 mg, 0.2 mmol), [1-(5-bromo-pyridin-3-yl)-ethyl]-methyl-amine (85.6 mg, 0.4 mmol), CuI (3.8 mg, 0.02 mmol), (1S,2S)-cyclohexane-1,2-diamine (4.5 mg, 0.04 mmol) and Cs2CO3 (130 mg, 0.4 mmol) were dissolved in 1,4-dioxane (5 mL). The reaction mixture was subject to microwave reaction at 150° C. for 2.5 hours before it was poured into H2O (15 mL) and extracted with EtOAc (2×10 mL). The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by prep-HPLC to yield the title compound (15 mg, 26%) as a white solid. MS: 316.2 (M+H+).

Workup

  1. customreaction at 150° C. for 2.5 hours before it
  2. extractionextracted with EtOAc (2×10 mL)
  3. washThe organic layer was washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-1b461168ca6145babb84c386cf430c38
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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