HCID 66819671, compound → HCID 66819831, compound

HRID 2045968Notes

Reaction equation

HRID 2045968 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH2:20][CH2:21][O:22]C3CCCCO3)=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1>CO>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH2:20][CH2:21][OH:22])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 66819671HCID 66819671, compound

Product 1

HCID 66819831HCID 66819831, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 590 mg (1.54 mmol) of 7-fluoro-3-phenyl-4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]isoquinolin-1(2H)-one in methanol (12 mL), 88 mg of p-toluenesuphonic acid (0.46 mmol) were added and the resulting mixture was heated at 55° C. for 2 hours. The solvent was removed under reduced pressure and the residue was diluted with dichloromethane and washed twice with aqueous sodium hydrogencarbonate saturated solution. The combined organic layer were dried over sodium sulphate and concentrated under reduced pressure to afford 438 mg of the title compound (95%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with dichloromethane
  3. washwashed twice with aqueous sodium hydrogencarbonate saturated solution
  4. dry with materialThe combined organic layer were dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7aecab9adf2496d97cc423cfa5a939c
Source dataset
uspto-grants-2013_11
Patent number
US08592416B2

Reaction notes

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