Triethylamine → 6-bromo-2-cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17330

Reaction equation

HRID 17330 reaction equation
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.[Br:16][C:17]1[C:18](F)=[C:19]2[O:23][C:22]([CH:24]3[CH2:26][CH2:25]3)=[N:21][C:20]2=[C:27]([C:30]#[N:31])[C:28]=1[CH3:29]>CS(C)=O>[Br:16][C:17]1[C:18]([N:5]2[CH2:6][CH2:7][C@H:3]([N:2]([CH3:8])[CH3:1])[CH2:4]2)=[C:19]2[O:23][C:22]([CH:24]3[CH2:25][CH2:26]3)=[N:21][C:20]2=[C:27]([C:30]#[N:31])[C:28]=1[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 510414276-Bromo-2-cyclopropyl-7-fluoro-5-methylbenzoxazole-4-carbonitrile

Product 1

HCID 685859546-bromo-2-cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-1,3-benzoxazole-4-carbonitrileYield 26.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

(3S)-3-(Dimethylamino)pyrrolidine (157 μl, 1.24 mmol) and triethylamine (348 μl, 2.50 mmol), were added to a dimethyl sulfoxide (5 ml) solution of 6-bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-77) (304 mg, 1.03 mmol). The system was purged with nitrogen and then sealed up and heated at 90° C. for 2 hours. After cooling, the solvent was evaporated away under reduced pressure, then the resulting residue was dissolved in chloroform, washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated away under reduced pressure, the resulting residue was washed with a mixed solvent of isopropyl ether and ethanol. The crystal was collected by filtration to obtain the entitled compound (106 mg, 26%) as a colorless solid.

Workup

  1. customThe system was purged with nitrogen
  2. customsealed up
  3. temperatureAfter cooling
  4. customthe solvent was evaporated away under reduced pressure
  5. dissolutionthe resulting residue was dissolved in chloroform
  6. washwashed with water and saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated away under reduced pressure
  9. washthe resulting residue was washed with a mixed solvent of isopropyl ether and ethanol
  10. filtrationThe crystal was collected by filtration

Sources & evidence

ORD record
ord-5089e38f65e34a179fddb8f70be12570
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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