Sodium Methoxide → HCID 72189585, compound

HRID 1487045Notes

Reaction equation

HRID 1487045 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:28][CH:29]([CH3:31])[CH3:30])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:15][C:14]=1F)(=[O:12])=[O:11].[CH3:32][O-:33].[Na+]>CO.ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:28][CH:29]([CH3:31])[CH3:30])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:15][C:14]=1[O:33][CH3:32])(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 72190831HCID 72190831, compound

Product 1

HCID 72189585HCID 72189585, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(2,4-dimethylphenyl)-2-fluoro-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide (358 mg, 0.478 mmol) in methanol (1 mL) at room temperature was added 25% sodium methoxide in methanol (109 uL, 0.478 mmol). The reaction mixture was stirred at room temperature for 2 hours, then heated to reflux for 1 hour. The reaction was quenched with water (1 mL) and the solvents removed in vacuo to give a yellow solid. The crude residue was dissolved in dichloromethane (DCM) (10 mL) and the organics washed with water (3×10 mL). The organics were passed through a hydrophobic frit and the filtrate evaporated to dryness to give a yellow oil. The crude was purified by mass directed autoprep (ammonium carbonate modifier). The solvent was evaporated under a stream of nitrogen to give the required product, 129 mg. LCMS [LCMS2] Rt 1.47 min, m/z (ES+) 462 (M+H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. customThe reaction was quenched with water (1 mL)
  4. customthe solvents removed in vacuo
  5. customto give a yellow solid
  6. washthe organics washed with water (3×10 mL)
  7. customthe filtrate evaporated to dryness
  8. customto give a yellow oil
  9. customThe crude was purified by mass
  10. customThe solvent was evaporated under a stream of nitrogen

Sources & evidence

ORD record
ord-9a0f67a7d8e94645be6aa551b22f3150
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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