Water → N-(2,4-dimethylphenyl)-N-(2-methylpropyl)-4-{[2-(4-morpholinyl)ethyl]oxy}benzenesulfonamide

HRID 1487043Notes

Reaction equation

HRID 1487043 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[I-].[K+].[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[N:17]([CH2:31][CH:32]([CH3:34])[CH3:33])[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29]O)=[CH:23][CH:22]=1)(=[O:20])=[O:19].O>CO>[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[N:17]([CH2:31][CH:32]([CH3:33])[CH3:34])[S:18]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:25][CH:26]=1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 8083MorpholineHCID 89875842N-(2,4-dimethylphenyl)-4-[(2-hydroxyethyl)oxy]-N-(2-methylpropyl)benzenesulfonamide

Product 1

HCID 72189584N-(2,4-dimethylphenyl)-N-(2-methylpropyl)-4-{[2-(4-morpholinyl)ethyl]oxy}benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

To a microwave vial was added morpholine (5.10 μL, 0.058 mmol), potassium iodide (19.26 mg, 0.116 mmol), [Cp*IrCl2]2 (0.639 mg, 0.580 μmol), N-(2,4-dimethylphenyl)-4-[(2-hydroxyethyl)oxy]-N-(2-methylpropyl)benzenesulfonamide (43.8 mg, 0.116 mmol), a stirrer bar and water (0.1 mL). The vial was then sealed and the mixture was heated to 150° C. by microwaves (Biotage Initiator) for 3 hours. Reaction mixture was then diluted with methanol (1 mL) and passed down a pre-conditioned sulfonic acid (SCX) solid phase extraction (SPE) cartridge, eluting with methanol and then 2N methanolic ammonia. The fractions from the methanolic ammonia wash were concentrated in vacuo and the residue purified by mass-directed autoprep, using a formic acid modifier. Product containing fractions were evaporated under a stream of nitrogen to provide product, 2.6 mg. LCMS [LCMS1] Rt 1.01 min, m/z (ES+) 447 (M+H).

Workup

  1. customThe vial was then sealed
  2. customReaction mixture
  3. extractiona pre-conditioned sulfonic acid (SCX) solid phase extraction (SPE) cartridge
  4. washeluting with methanol
  5. washThe fractions from the methanolic ammonia wash
  6. concentrationwere concentrated in vacuo
  7. customthe residue purified by mass-directed autoprep
  8. additionProduct containing fractions
  9. customwere evaporated under a stream of nitrogen
  10. customto provide product, 2.6 mg

Sources & evidence

ORD record
ord-2acd454b5dee4cca974c26fe6ea1b5cc
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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