Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 58431986, compound

HRID 512681Notes

Reaction equation

HRID 512681 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[O:14][N:13]=[C:12]([CH:15]([O:31]C(OCC)C)[CH:16]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:21][CH:20]=3)[O:17][CH3:18])[N:11]=2)=[CH:4][C:3]=1[O:37][CH3:38].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[Br:1][C:2]1[C:3]([O:37][CH3:38])=[CH:4][C:5]([C:10]2[O:14][N:13]=[C:12]([CH:15]([OH:31])[CH:16]([O:17][CH3:18])[C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:21][CH:20]=3)[N:11]=2)=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 584319924-(4-(2-(5-(4-Bromo-3,5-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-(1-ethoxyethoxy)-1-methoxyethyl)phenyl)morpholine

Product 1

HCID 58431986HCID 58431986, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(4-(2-(5-(4-bromo-3,5-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-(1-ethoxyethoxy)-1-methoxyethyl)phenyl)morpholine (0.335 g, 0.57 mmol) in MeOH (15 mL) was added pyridinium para-toluenesulfonate (0.15 g, 0.6 mmol) and the mixture was stirred at room temperature for 16.5 hrs. The reaction was then heated at 40° C. for 6 hrs, cooled to room temp, and concentrated in vacuo. The residue was dissolved in EtOAc and washed with H2O, saturated NaHCO3 and brine then dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (50-60% EtOAc-hexanes) gave 1-(5-(4-bromo-3,5-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-methoxy-2-(4-morpholinophenyl)ethanol as a colorless residue (0.234, 79% yield).

Workup

  1. temperatureThe reaction was then heated at 40° C. for 6 hrs
  2. temperaturecooled to room temp
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O, saturated NaHCO3 and brine
  6. dry with materialthen dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography (50-60% EtOAc-hexanes)

Sources & evidence

ORD record
ord-47951b372c874e21bb097f1931aa05a7
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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