Triethylamine → 7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17436

Reaction equation

HRID 17436 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.F[C:17]1[C:18]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:19]([CH3:34])[C:20]([C:32]#[N:33])=[C:21]2[C:25]=1[O:24][C:23]([C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][CH:30]=1)=[N:22]2>CS(C)=O>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:17]2[C:18]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:19]([CH3:34])[C:20]([C:32]#[N:33])=[C:21]3[C:25]=2[O:24][C:23]([C:26]2[N:27]([CH3:31])[CH:28]=[CH:29][CH:30]=2)=[N:22]3)[CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 510399657-fluoro-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 510425497-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 27%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

(3S)-3-(Dimethylamino)pyrrolidine (53 μl, 0.42 mmol) and triethylamine (100 μl) were added to a dimethyl sulfoxide (2 ml) solution of 7-fluoro-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-166) (69 mg, 0.21 mmol). The system was purged with nitrogen, then sealed up, and heated at 110° C. for 3.5 hours. After cooling, the solvent was evaporated away under reduced pressure, the resulting residue was dissolved in chloroform and washed with water. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated away under reduced pressure, and the resulting residue was separated and purified by preparative TLC to obtain a main product. This was washed with a mixed solvent of isopropyl ether and ethanol, and the solid was collected by filtration to obtain the entitled compound (24 mg, 27%) 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
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated away under reduced pressure
  9. customthe resulting residue was separated
  10. custompurified by preparative TLC
  11. customto obtain a main product
  12. washThis was washed with a mixed solvent of isopropyl ether and ethanol
  13. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-50453e31faea4828b575af8b59791766
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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