HCID 68585893, compound → 7-fluoro-5-methyl-2-[methyl(1H-1,2,4-triazol-5-ylmethyl)amino]-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17433Notes

Reaction equation

HRID 17433 reaction equation
[F:1][C:2]1[C:3]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:4]([CH3:30])[C:5]([C:28]#[N:29])=[C:6]2[C:10]=1[O:9][C:8]([N:11]([CH3:27])[CH2:12][C:13]1[N:14](CC3C=CC(OC)=CC=3)[N:15]=[CH:16][N:17]=1)=[N:7]2>FC(F)(F)C(O)=O>[F:1][C:2]1[C:3]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:4]([CH3:30])[C:5]([C:28]#[N:29])=[C:6]2[C:10]=1[O:9][C:8]([N:11]([CH3:27])[CH2:12][C:13]1[NH:14][N:15]=[CH:16][N:17]=1)=[N:7]2

Participants

3

Reactant 1

HCID 68585893HCID 68585893, compound

Product 1

HCID 685848557-fluoro-5-methyl-2-[methyl(1H-1,2,4-triazol-5-ylmethyl)amino]-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 97.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7-Fluoro-2-[N-[[2-(4-methoxybenzyl)-2-H-[1,2,4]triazol-3-yl]methyl]methylamino]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-164) (0.33 g, 0.68 mmol) was dissolved in trifluoroacetic acid (5 ml), and stirred at room temperature for 16 hours, then at an external temperature of about 60° C. for 6 hours. The solvent was evaporated away under reduced pressure, then ethyl acetate and aqueous sodium hydrogencarbonate solution were added, and the organic layer was separated. After drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1) to obtain a colorless solid (0.24 g, 97%).

Workup

  1. waitat an external temperature of about 60° C. for 6 hours
  2. customThe solvent was evaporated away under reduced pressure
  3. additionethyl acetate and aqueous sodium hydrogencarbonate solution were added
  4. customthe organic layer was separated
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-63d3818bb09c4d659eede15646fa4e51
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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