Dimethylformamide → HCID 57559893, compound

HRID 423238Notes

Reaction equation

HRID 423238 reaction equation
[H-].[Na+].CN(C=O)C.[CH2:8]([O:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[SH:22])[CH2:9][CH3:10].Br[CH:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][N:31]=2)[CH2:26][CH2:25]1>O>[CH2:8]([O:11][C:12]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:14][C:13]=1[S:22][CH:24]1[CH2:25][CH2:26][N:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][N:31]=2)[CH2:28][CH2:29]1)[CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 23159128HCID 23159128, compoundHCID 23159146Pyridine, 2-(4-bromo-1-piperidinyl)-5-(trifluoromethyl)-

Product 1

HCID 57559893HCID 57559893, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 60% sodium hydride was added, with chilling on ice, to the DMF (7 ml) solution of the chemical compound (46) (0.62 g), it was warmed to room temperature, and was then stirred for 30 minutes. After the chemical compound (48) (0.74 g) was added to the mixture, it was heated to 100° C., and was then stirred for 1 hour. After the mixture was cooled, it was poured into water, and was then subjected to extraction with ethyl acetate. After its organic layer was washed with water, and was then dried with anhydrous magnesium sulfate, it was filtered, and was then concentrated under reduced pressure. Its residue was purified by column chromatography to produce the chemical compound mentioned in the above title (0.90 g).

Workup

  1. temperaturewas heated to 100° C.
  2. stirringwas then stirred for 1 hour
  3. temperatureAfter the mixture was cooled
  4. extractionwas then subjected to extraction with ethyl acetate
  5. washAfter its organic layer was washed with water
  6. dry with materialwas then dried with anhydrous magnesium sulfate, it
  7. filtrationwas filtered
  8. concentrationwas then concentrated under reduced pressure
  9. customIts residue was purified by column chromatography
  10. customto produce the chemical compound

Sources & evidence

ORD record
ord-822ab3ae79754bbab2fe22e596f15149
Source dataset
uspto-grants-2012_01
Patent number
US08101768B2

Reaction notes

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