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

HRID 17356
Notes
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Reaction equation

HRID 17356 reaction equation
F[C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:4]([CH3:19])[C:5]([C:17]#[N:18])=[C:6]2[C:10]=1[O:9][C:8]([C:11]([CH3:16])([CH3:15])[CH2:12][O:13][CH3:14])=[N:7]2.C(N(CC)CC)C.[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][NH:37][CH2:36]1.C(OCC)(=O)C>CS(C)=O.O>[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][N:37]([C:2]2[C:3]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:4]([CH3:19])[C:5]([C:17]#[N:18])=[C:6]3[C:10]=2[O:9][C:8]([C:11]([CH3:16])([CH3:15])[CH2:12][O:13][CH3:14])=[N:7]3)[CH2:36]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685855317-Fluoro-2-(2-methoxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685859187-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-2-[2-methoxy-1,1-dimethylethyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile
Yield 35%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

7-Fluoro-2-(2-methoxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-100) (40 mg, 0.12 mmol) was dissolved in dimethyl sulfoxide (0.8 ml), triethylamine (23 μl, 0.17 mmol) and (3S)-3-(dimethylamino)pyrrolidine (18 μl, 0.14 mmol) were added, followed by stirring at 90° C. for 3 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 preparative thin-layer silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (10:1, v/v), and washed with n-hexane and ethyl acetate to obtain the entitled compound (18 mg, 35%) as a white 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 (10:1
  6. washv/v), and washed with n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-680d0e84eb3648ddb9730fdb30f70cc1
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737166B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes