Sodium hydride → HCID 71543642, compound

HRID 1746409Notes

Reaction equation

HRID 1746409 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+].Br[CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1>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][CH2:28][C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[CH:14]=1)(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6427994-(Bromomethyl)pyridineHCID 86731583HCID 86731583, compound

Product 1

HCID 71543642HCID 71543642, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

N-(2,4-dimethylphenyl)-3-(hydroxymethyl)-N-isobutylbenzenesulfonamide (50 mg, 0.144 mmol) and Sodium hydride (60% in Mineral Oil) (6.33 mg, 0.158 mmol) were dissolved in N,N-Dimethylformamide (DMF) (3 mL). To this solution was added 4-(bromomethyl)pyridine (24.75 mg, 0.144 mmol), and the reaction heated to 60° C. and left to stir for 30 min. The reaction solution concentrated on the Biotage V10 and then extracted the crude product to the organic phase of an aqueous work up between ethyl acetate (15 mL) and water (15 mL). The organic phase was separated (hydrophobic frit) and then concentrated in vacuo. The sample was dissolved in 1:1 MeOH:DMSO 1 mL and purified by mass directed autoprep on Sunfire C18 column using acetonitrile:water with a formic acid modifier. The solvent was evaporated in vacuo. The crude product was run through an NH2 SPE column (1 g) eluting with methanol, to remove the formic acid. The product was then dried under a stream of nitrogen on a Radleys blow down unit, to give the final product, 13.5 mg.

Workup

  1. waitleft
  2. concentrationThe reaction solution concentrated on the Biotage
  3. extractionand then extracted the crude product to the organic phase of an aqueous work up between ethyl acetate (15 mL) and water (15 mL)
  4. customThe organic phase was separated (hydrophobic frit)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe sample was dissolved in 1:1 MeOH
  7. customDMSO 1 mL and purified by mass
  8. customThe solvent was evaporated in vacuo
  9. washeluting with methanol
  10. customto remove the formic acid
  11. customThe product was then dried under a stream of nitrogen on a Radleys blow down unit

Sources & evidence

ORD record
ord-360378263d014be49bbc8f72346f4473
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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