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

HRID 17350Notes

Reaction equation

HRID 17350 reaction equation
F[C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([CH3:21])[C:5]([C:19]#[N:20])=[C:6]2[C:10]=1[O:9][C:8](/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:7]2.C(N(CC)CC)C.[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][NH:39][CH2:38]1.C(OCC)(=O)C>CS(C)=O.O>[CH3:35][N:36]([CH3:42])[C@H:37]1[CH2:41][CH2:40][N:39]([C:2]2[C:3]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:4]([CH3:21])[C:5]([C:19]#[N:20])=[C:6]3[C:10]=2[O:9][C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7]3)[CH2:38]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685854757-fluoro-5-methyl-6-phenyl-2-[(E)-2-phenylethenyl]-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685865437-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-[(E)-2-phenylethenyl]-1,3-benzoxazole-4-carbonitrileYield 65%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

7-Fluoro-5-methyl-6-phenyl-2-[(E)-2-phenylethenyl]-1,3-benzoxazole-4-carbonitrile (I-92) (200 mg, 0.56 mmol) was dissolved in dimethylsulfoxide (2 ml), triethylamine (190 μl, 1.35 mmol) and (3S)-3-(dimethylamino)pyrrolidine (86 μl, 0.68 mmol) were added, followed by stirring at 90° C. for 15 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (50:1, v/v), recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (163 mg, 65%) as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated away
  5. washeluted with a mixed solvent of chloroform/methanol (50:1
  6. customv/v), recrystallized
  7. custompurified with n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-6c364dbff3254fda91f057de3d5af857
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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