Hydrochloric Acid → HCID 71543439, compound

HRID 1746416Notes

Reaction equation

HRID 1746416 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][O:28]C4CCCCO4)=[CH:21][C:20]=3[CH3:35])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:40])[O:4][N:3]=1.Cl.O1CCOCC1>O1CCCC1.CO>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][OH:28])=[CH:21][C:20]=3[CH3:35])[CH2:36][CH:37]([CH3:39])[CH3:38])(=[O:16])=[O:17])=[CH:11][CH:10]=2)=[C:5]([CH3:40])[O:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86731591HCID 86731591, compound

Product 1

HCID 71543439HCID 71543439, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutyl-N-(2-methyl-4-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)phenyl)benzenesulfonamide (51.2 mg, 0.089 mmol) in tetrahydrofuran (THF) (4 mL) stirred at room temperature was added a solution of 4M HCl in dioxane (4 mL, 16.00 mmol). The reaction mixture was stirred at room temperature for 1 hour. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the crude product. The sample was dissolved in 1:1 MeOH:DMSO 1 mL and purified by Open Access Mass Directed AutoPrep on Sunfire C18 column using Acetonitrile Water with a Formic acid modifier. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the required product, 27 mg as colourless oil which solidified. LCMS (M+1) 489, RT 1.14 mins.

Workup

  1. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
  2. customto give the crude product
  3. customDMSO 1 mL and purified by Open Access Mass Directed AutoPrep on Sunfire C18 column
  4. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-408bacdec5dc4f3da2b16446c2c6c295
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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