Sodium hydride → HCID 86594270, compound

HRID 1182249Notes

Reaction equation

HRID 1182249 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[S:10]([NH:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[C:16]([N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[C:15]=1[CH3:27])(=[O:12])=[O:11].[H-].[Na+].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>CN(C=O)C>[Cl:8][C:7]1[C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])=[C:3]([S:10]([NH:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[C:16]([N:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)[C:15]=2[CH3:27])(=[O:11])=[O:12])[CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 59643655HCID 59643655, compound

Product 1

HCID 86594270HCID 86594270, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 40 (69 mg, 0.16 mmol) in DMF at 0° C. was added NaH (60% in mineral oil, 14 mg, 0.35 mmol). The mixture was stirred for 10 min at 0° C. before the addition of methanesulfonyl chloride (22 mg, 0.19 mmol). The resulting mixture was then stirred at room temperature overnight. The reaction was quenched with a few drops of dilute HCl and then diluted with EtOAc (60 mL). The organic layer was washed with water (2×30 mL) and brine (30 mL) and the volatiles were removed by evaporation on a rotavap. The residue was purified on a silica gel column (15% to 30% EtOAc in hexanes) to yield the title compounds as an off-white solid (10 mg ESI [M+H+]=506.12).

Workup

  1. customThe reaction was quenched with a few drops of dilute HCl
  2. additiondiluted with EtOAc (60 mL)
  3. washThe organic layer was washed with water (2×30 mL) and brine (30 mL)
  4. customthe volatiles were removed by evaporation on a rotavap
  5. customThe residue was purified on a silica gel column (15% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8d13cf7ea3d74f2db516021903fd3e10
Source dataset
uspto-grants-2007_10
Patent number
US07288538B2

Reaction notes

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