HCID 118062775, compound → HCID 118062339, compound

HRID 920822Notes

Reaction equation

HRID 920822 reaction equation
C(OC([NH:8][CH:9]([C:27]([F:30])([F:29])[F:28])[CH2:10][N:11]1[C:15]([C:16](OCC)=[O:17])=[C:14]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:13]([I:26])=[N:12]1)=O)(C)(C)C>Cl.O1CCOCC1>[I:26][C:13]1[C:14]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:15]2[C:16](=[O:17])[NH:8][CH:9]([C:27]([F:30])([F:29])[F:28])[CH2:10][N:11]2[N:12]=1

Participants

4

Reactant 1

HCID 118062775HCID 118062775, compound

Product 1

HCID 118062339HCID 118062339, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Intermediate 346A (3 g, 5.46 mmol) was dissolved in 4 M HCl in 1,4-dioxane (50 mL) and stirred at RT for 2 h. The volatiles were removed under reduced pressure, and the crude residue was dissolved in EtOAc (250 mL) and washed with an aq. solution of NaHCO3, then dried over Na2SO4 and concentrated under reduced pressure. The crude was dissolved in EtOH (25 mL) and stirred at 60° C. for 16 h. Ethanol was removed under reduced pressure and the resulting residue was stirred with hexanes for 15 min. The triturated solid was filtered and dried to afford Intermediate 346B (0.96 g, 41.4%) as an off-white solid. MS(ES): −m/z=404.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.34 (d, J=4.5 Hz, 1H), 4.84-4.73 (m, 2H), 4.71-4.60 (m, 1H), 4.34-4.20 (m, 2H), 1.32-1.23 (m, 3H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe crude residue was dissolved in EtOAc (250 mL)
  3. washwashed with an aq. solution of NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe crude was dissolved in EtOH (25 mL)
  7. stirringstirred at 60° C. for 16 h
  8. customEthanol was removed under reduced pressure
  9. stirringthe resulting residue was stirred with hexanes for 15 min
  10. filtrationThe triturated solid was filtered
  11. customdried

Sources & evidence

ORD record
ord-116235e3aba54d1eb9683152fa1bfe75
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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