2-(Methylamino)ethanol → 7-Fluoro-2-[(2-hydroxyethyl)(methyl)amino]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17413Notes

Reaction equation

HRID 17413 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][CH2:32][CH2:33][OH:34]>ClCCl>[F:11][C:10]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([CH3:18])[C:7]([C:19]#[N:20])=[C:5]2[C:4]=1[O:3][C:2]([N:31]([CH2:32][CH2:33][OH:34])[CH3:30])=[N:6]2

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanol2×HCID 81531DiisopropylethylamineHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685854957-Fluoro-2-[(2-hydroxyethyl)(methyl)amino]-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 (0.13 ml, 0.76 mmol) and N-methylethanolamine (62.0 μl, 0.78 mmol) were added. After heating under reflux for 3 hours, N-methylethanolamine (62.0 μl, 0.78 mmol) was added. After heated under reflux for 3 hours, this was diluted with dichloromethane. After washing with water and 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=40:1) to obtain a pale yellow oil (0.21 g, 93%).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter heated
  4. temperatureunder reflux for 3 hours
  5. washAfter washing with water
  6. dry with materialdrying 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:methanol=40:1)

Sources & evidence

ORD record
ord-6af7a1412ed5469ab03933966d9e2f54
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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