Pyridine → HCID 88539113, compound

HRID 587830Notes

Reaction equation

HRID 587830 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[N:30]1[CH:34]=[N:33][CH:32]=[N:31]1)[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH2:25][CH3:26])=[O:6].N1C=CC=CC=1.[C:41](Cl)(=[O:45])[O:42][CH2:43]C>O1CCCC1.O>[CH3:43][O:42][C:41](=[O:45])[NH:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[NH:7][C:8]2[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:21])([F:22])[F:23])[C:16]([F:18])([F:19])[F:17])=[CH:10][C:9]=2[CH2:25][CH3:26])[CH:27]=[CH:28][C:29]=1[N:30]1[CH:34]=[N:33][CH:32]=[N:31]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 50940482HCID 50940482, compound

Product 1

HCID 88539113HCID 88539113, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methyl-phenyl]-4-(1H-1,2,4-triazol-1-yl)benzamide (0.2 g) and pyridine (0.05 g) were dissolved in tetrahydrofuran (5 ml). To the solution, ethyl chlorocarbonate (0.04 g) was added under ice cooling. After adjusting to room temperature, the mixture was stirred for 1 hr. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with water and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain methyl[5-{[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro-propan-2-yl)-6-methylphenyl]carbamoyl}-2-(1H-1,2,4-triazol-1-yl)phenyl]carbamate (0.14 g, yield 58%).

Workup

  1. customAfter adjusting to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtering off the drying agent
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain a crude product
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-77a1702ed49b4a62a502774ffb8ef87f
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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