Trimethylsilyl iodide → HCID 178448112, compound

HRID 49226Notes

Reaction equation

HRID 49226 reaction equation
C[Si](I)(C)C.[CH:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH2:26][C:27]3[CH:28]=[N:29][C:30]([O:33]C)=[CH:31][CH:32]=3)=[CH:18][N:17]=2)[CH2:11][CH2:10]1)([CH3:8])[CH3:7]>C(Cl)(Cl)Cl>[CH:6]([C@H:9]1[CH2:10][CH2:11][C@H:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH2:26][C:27]3[CH:28]=[N:29][C:30]([OH:33])=[CH:31][CH:32]=3)=[CH:18][N:17]=2)[CH2:13][CH2:14]1)([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 178489834HCID 178489834, compound

Product 1

HCID 178448112HCID 178448112, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Under a N2 atmosphere, 122 μl (0.90 mmol) of trimethylsilyl iodide are added to a solution of 351 mg (0.90 mmol) of trans 1-(4-isopropyl-cyclohexylamino)-4-[(6-methoxy-pyridin-3-yl)-methyl]-isoquinoline in 8 ml of chloroform, and stirred for 14 h at 60° C., then a further 122 μl of trimethylsilyl iodide are added and stirring is again effected for 3 h at 60° C. The mixture is cooled, the supernatant solution decanted from the solid, rinsed with a little chloroform and the chloroform phases discarded. The residue is dissolved by stirring in 40 ml of methylene chloride, 10 ml of methanol, 5 ml of EtOAc, 5 ml of saturated NaHCO3 solution and 5 ml of water. After adding more water, the organic phase is separated and washed with water and brine. The aqueous phases are extracted 3 more times with EtOAc. Drying (Na2SO4), concentrating by evaporation and crystallisation from hexane yield trans 1-(4-isopropyl-cyclohexylamino)-4-[(6-hydroxy-pyridin-3-yl)-methyl]-isoquinoline from the organic phases; FAB-MS: (M+H)+=376; TLC(acetone/CH2Cl2 3:2): Rf=0.13.

Workup

  1. stirringstirring
  2. waitis again effected for 3 h at 60° C
  3. temperatureThe mixture is cooled
  4. customthe supernatant solution decanted from the solid
  5. washrinsed with a little chloroform
  6. dissolutionThe residue is dissolved
  7. stirringby stirring in 40 ml of methylene chloride
  8. additionAfter adding more water
  9. customthe organic phase is separated
  10. washwashed with water and brine
  11. extractionThe aqueous phases are extracted 3 more times with EtOAc
  12. dry with materialDrying (Na2SO4)
  13. concentrationconcentrating by evaporation and crystallisation from hexane

Sources & evidence

ORD record
ord-23bba0bbd1674f22a2dac5d1b8928c3b
Source dataset
uspto-grants-2004_03
Patent number
US06706731B2

Reaction notes

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