Sodium hydride → HCID 72189583, compound

HRID 1487042Notes

Reaction equation

HRID 1487042 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=1)(=[O:12])=[O:11].[H-].[Na+].CS(O[CH2:32][CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)(=O)=O>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][CH2:32][CH:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH:14]=1)(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15166436Oxan-4-ylmethyl methanesulfonateHCID 86731583HCID 86731583, compound

Product 1

HCID 72189583HCID 72189583, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

N-(2,4-dimethylphenyl)-3-(hydroxymethyl)-N-isobutylbenzenesulfonamide (40 mg, 0.115 mmol) and sodium hydride (4.14 mg, 0.173 mmol) were dissolved in anhydrous N,N-dimethylformamide (DMF) (3 mL). The solution was stirred for 10 minutes under nitrogen at 20° C. (Tetrahydro-2H-pyran-4-yl)methyl methanesulfonate (49 mg, 0.252 mmol) was added to the solution, which was stirred overnight at 20° C. under nitrogen. The reaction was concentrated under vacuum (Biotage V10) to give the crude product. This was then partitioned between ethyl acetate (10 mL) and water (10 mL). The organic layer was washed with water (5×5 mL), passed through a hydrophobic frit and concentrated in vacuo. The crude product was then dissolved in a minimum of DCM and purified by silica (Si) chromatography using a 0-25% ethyl acetate-cyclohexane gradient. The relevant fractions were combined and condensed to provide the required product, 28 mg. LCMS [LCMS1] Rt 1.46 min, m/z (ES+) 446 (M+H).

Workup

  1. additionwas added to the solution, which
  2. concentrationThe reaction was concentrated under vacuum (Biotage V10)
  3. customto give the crude product
  4. customThis was then partitioned between ethyl acetate (10 mL) and water (10 mL)
  5. washThe organic layer was washed with water (5×5 mL)
  6. concentrationconcentrated in vacuo
  7. dissolutionThe crude product was then dissolved in a minimum of DCM
  8. custompurified by silica (Si) chromatography
  9. customcondensed

Sources & evidence

ORD record
ord-3dbe0f23231341b5819b3b37c40d14d0
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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