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

HRID 17500Notes

Reaction equation

HRID 17500 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[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=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[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[N:22]3)[CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685843947-Fluoro-5-methyl-6-phenyl-2-(pyridin-3-yl)-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 510425477-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(pyridin-3-yl)-1,3-benzoxazole-4-carbonitrileYield 69.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

(3S)-3-(Dimethylamino)pyrrolidine (123 μl, 0.970 mmol) and triethylamine (135 μl, 0.970 mmol) were added to a dimethyl sulfoxide (6 ml) solution of 7-fluoro-5-methyl-6-phenyl-2-(pyridin-3-yl)-1,3-benzoxazole-4-carbonitrile (I-209) (213 mg, 0.647 mmol), followed by stirring in an oil bath at 95° C. for 2 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (100 ml), then washed with water (50 ml) and saturated brine (50 ml). After drying over anhydrous sodium sulfate and concentration, the residue was purified by silica gel column chromatography (eluent, chloroform/methanol=10:1), and the eluate was recrystallized from isopropanol to obtain the entitled compound (190 mg, 69.4%) as a yellow crystal.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (100 ml)
  4. washwashed with water (50 ml) and saturated brine (50 ml)
  5. dry with materialAfter drying over anhydrous sodium sulfate and concentration
  6. customthe residue was purified by silica gel column chromatography (eluent, chloroform/methanol=10:1)
  7. customthe eluate was recrystallized from isopropanol

Sources & evidence

ORD record
ord-347080675b4e4e64a3bb3101a823ae8e
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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