Diisopropylethylamine → 2-(N-tert-butyl-N-methylamino)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17411

Reaction equation

HRID 17411 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.C(N(C(C)C)CC)(C)C.[CH3:30][NH:31][C:32]([CH3:35])([CH3:34])[CH3:33]>ClCCl>[C:32]([N:31]([C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1)[CH3:30])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 84552N-Methyl-tert-butylamine2×HCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685839942-(N-tert-butyl-N-methylamino)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (0.20 g, 0.70 mmol) was dissolved in dichloromethane (10 ml), and diisopropylethylamine (0.15 ml, 0.88 mmol) and N-methyl-tert-butylamine (0.10 ml, 0.84 mmol) were added. After heating under reflux for 3 hours, N-methyl-tert-butylamine (50.0 μl, 0.42 mmol) was added, followed by heating under reflux for 2 hours. This was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane) to obtain a pale yellow solid (0.22 g, 0.65 mmol, 93%).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 hours
  3. temperatureby heating
  4. temperatureunder reflux for 2 hours
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-0b6aaea06b77418ebe65367fb21e66c5
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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