Sodium hydride → HCID 15392242, compound

HRID 362531Notes

Reaction equation

HRID 362531 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][C:28]([C:34]#[N:35])=[CH:29][CH:30]=4)[CH:25]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:38][S:39](Cl)(=[O:41])=[O:40]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([S:39]([CH3:38])(=[O:41])=[O:40])[C:22]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][C:28]([C:34]#[N:35])=[CH:29][CH:30]=4)[CH:25]=3)=[O:23])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 15392241HCID 15392241, compound

Product 1

HCID 15392242HCID 15392242, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-[4-[(1-t-Butoxycarbonyl-4-piperidyl)oxy]phenyl]-7-cyano-2-naphthalenecarboxamide obtained in Reference Example 47 (200 mg) was dissolved in 4 ml of DMF, 52 mg of sodium hydride (content 60%) was added to the solution, and the mixture was stirred at room temperature for 20 minutes. While stirring at 0° C., 1 ml dimethylformamide solution of 100 ml methanesulfonyl chloride was added dropwise to the reaction solution, followed by 1 day of stirring at room temperature. The reaction solution was evaporated and ethyl acetate was added to the resulting residue. The mixture was washed with saturated sodium bicarbonate aqueous solution and 10% citric acid aqueous solution in that order, dried over anhydrous sodium sulfate, and then evaporated. The resulting residue was purified by silica gel column chromatography using hexane:ethyl acetate (8:2-7:3) as the eluent to give 143 mg of N-[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]phenyl]-7-cyano-N-methylsulfonyl-2-naphthalenecarboxamide.

Workup

  1. stirringWhile stirring at 0° C.
  2. waitfollowed by 1 day
  3. stirringof stirring at room temperature
  4. customThe reaction solution was evaporated
  5. additionethyl acetate was added to the resulting residue
  6. washThe mixture was washed with saturated sodium bicarbonate aqueous solution and 10% citric acid aqueous solution in that order
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-17a1126373954a6f9c86c306702124d5
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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