Sodium Iodide → HCID 59375501, compound

HRID 2193026Notes

Reaction equation

HRID 2193026 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]2[C:6]([NH:15][CH:16]([CH3:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.[I-:24].[Na+].CN[C@H]1[C@H](NC)CCCC1>[Cu]I.C(O)CCC>[I:24][C:2]1[CH:23]=[CH:22][C:5]2[C:6]([NH:15][CH:16]([CH3:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 25097260HCID 25097260, compound

Product 1

HCID 59375501HCID 59375501, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

9-bromo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (120 mg, 0.31 mmol), copper(I) iodide (5.9 mg, 0.031 mmol), and sodium iodide (93 mg, 0.62 mmol) were combined in a vial. Butan-1-ol (1.0 ml) and trans-(1R,2R)—N,N-bismethyl-1,2-cyclohexanediamine (9.9 μl, 0.062 mmol) were added, and the resulting suspension was purged with argon (subsurface bubbling) for 5 min. The reaction mixture was heated to 130° C., and stirred for 22 hours. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate (40 mL) and brine (40 mL). The organic layer was washed with additional brine (1×40 ml). The first aqueous layer was back-extracted with ethyl acetate (1×40 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (solid SiO2 loading) using an EtOAc/Hexanes gradient to afford 9-iodo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one. LRMS (ESI) calc'd for (C18H20IN3O) [M+H]+, 422.1; found 422.0.

Workup

  1. customthe resulting suspension was purged with argon (subsurface bubbling) for 5 min
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was partitioned between ethyl acetate (40 mL) and brine (40 mL)
  4. washThe organic layer was washed with additional brine (1×40 ml)
  5. extractionThe first aqueous layer was back-extracted with ethyl acetate (1×40 mL)
  6. dry with materialThe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (solid SiO2 loading)

Sources & evidence

ORD record
ord-4b45a4dd55924f7694052af73915113f
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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