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

HRID 17473Notes

Reaction equation

HRID 17473 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:31]=[N:30][CH:29]=[CH:28][N:27]=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:31]=[N:30][CH:29]=[CH:28][N:27]=2)=[N:22]3)[CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685858077-Fluoro-5-methyl-6-phenyl-2-(pyrazin-2-yl)-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685848897-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(pyrazin-2-yl)-1,3-benzoxazole-4-carbonitrileYield 38.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

(3S)-3-(Dimethylamino)pyrrolidine (93.4 μl, 0.736 mmol) and triethylamine (121 μl, 0.866 mmol) were added to a dimethyl sulfoxide (4 ml) solution of 7-fluoro-5-methyl-6-phenyl-2-(pyrazin-2-yl)-1,3-benzoxazole-4-carbonitrile (I-187) (143 mg, 0.433 mmol), followed by stirring in an oil bath at 95° C. for 0.2 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (100 ml), washed with saturated brine (50 ml). After drying over anhydrous sodium sulfate, the solvent was evaporated away, and the resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=9:1), the eluate was recrystallized from isopropanol to obtain the entitled compound (71.0 mg, 38.6%) as a pale yellow acicular crystal.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (100 ml)
  4. washwashed with saturated brine (50 ml)
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=9:1)
  8. customthe eluate was recrystallized from isopropanol

Sources & evidence

ORD record
ord-3c628e19145d41678b001e2745aa5a87
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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