Sodium hydride → HCID 19369632, compound

HRID 849231Notes

Reaction equation

HRID 849231 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([S:8][CH2:9][C:10]2[N:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[C:12]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:11]=2)=[N:5][N:4]=1)[CH3:2].[H-].[Na+].CS(O[CH2:37][C:38]1[CH:43]=[C:42]([N+:44]([O-:46])=[O:45])[CH:41]=[C:40]([CH3:47])[CH:39]=1)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[C:19]([O:18][C:17]([N:16]([C:14]1[CH:13]=[C:12]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[CH:11]=[C:10]([CH2:9][S:8][C:6]2[S:7][C:3]([CH2:1][CH3:2])=[N:4][N:5]=2)[N:15]=1)[CH2:37][C:38]1[CH:43]=[C:42]([N+:44]([O-:46])=[O:45])[CH:41]=[C:40]([CH3:47])[CH:39]=1)=[O:23])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 19369623HCID 19369623, compoundHCID 19369746HCID 19369746, compound

Product 1

HCID 19369632HCID 19369632, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl N-[6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholino-2-pyridyl]carbamate (200 mg) obtained in Example 1-(5) in dimethylformamide (2 ml), 60% sodium hydride (30 mg) was added under cooling with ice, followed by stirring at the same temperature for 30 minutes. A solution of 3-methyl-5-nitrobenzyl methanesulfonate (283 mg) in dimethylformamide (1 ml), was added to the reaction solution, followed by stirring at room temperature overnight. The reaction solution was diluted with ethyl acetate, washed with water and a saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane/ethyl acetate=1:1) to obtain the above identified compound (314 mg) as a pale yellow oily substance.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringby stirring at room temperature overnight
  4. washwashed with water
  5. dry with materiala saturated sodium hydrogen carbonate aqueous solution and dried over anhydrous magnesium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (heptane/ethyl acetate=1:1)
  8. customto obtain the

Sources & evidence

ORD record
ord-92336094ebf74877ad557a523fd458d4
Source dataset
uspto-grants-2000_01
Patent number
US06011039

Reaction notes

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