Dimethylformamide → HCID 3003628, compound

HRID 2395198Notes

Reaction equation

HRID 2395198 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].CN(C)C=O.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C@:21]1([O:45][CH2:44]1)[C@H:22]([N:24]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]([F:42])([F:41])[CH:38]([F:40])[F:39])=[CH:31][CH:30]=2)[C:25]1=[O:43])[CH3:23]>O>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C@@:21]([OH:45])([CH2:44][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)[C@H:22]([N:24]1[CH2:28][CH2:27][N:26]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH2:36][C:37]([F:41])([F:42])[CH:38]([F:39])[F:40])=[CH:33][CH:34]=2)[C:25]1=[O:43])[CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 86753166HCID 86753166, compound

Product 1

HCID 3003628HCID 3003628, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.41 g of 1H-1,2,4-triazole, 0.19 g of 60% sodium hydride in oil and 12 ml of dimethylformamide was stirred at room temperature for 20 minutes, and added with 0.85 g of 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2-imidazolidinone obtained in Step 3 and the resultant mixture was heated at 60° C. for 4 hours. After cooling, 20 ml of water was added to the reaction mixture and the mixture was extracted with 80 ml of ethyl acetate. The extract was washed with 20 ml of a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (gradient eluent: hexane:ethyl acetate=1:2→1:5) to give 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(2,2,3,3-tetrafluoropropoxy) phenyl]-2-imidazolidinone (Compound B) as a colorless powder.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with 80 ml of ethyl acetate
  3. washThe extract was washed with 20 ml of a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (gradient eluent: hexane:ethyl acetate=1:2→1:5)

Sources & evidence

ORD record
ord-bb3ca4c2357e45bdbec68e2734380f09
Source dataset
uspto-grants-1998_09
Patent number
US05814324

Reaction notes

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