Pyridine → HCID 68584949, compound

HRID 17400Notes

Reaction equation

HRID 17400 reaction equation
CN(C)[C@H]1CCN(C2[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:10]([CH3:21])[C:11]([C:19]#[N:20])=[C:12]3C=2O[C:14]([NH:17][CH3:18])=[N:13]3)C1.[C:29](Cl)(=[O:31])[CH3:30].[CH:33]([N:36]([CH:39]([CH3:41])[CH3:40])[CH2:37]C)(C)C.[N:42]1[CH:47]=CC=CC=1.[O:48]1CC[CH2:50][CH2:49]1>C(OCC)(=O)C.O>[C:19]([C:11]1[C:12]2[N:13]=[C:14]([N:17]([CH3:18])[C:49](=[O:48])[CH3:50])[O:31][C:29]=2[C:30]([N:42]2[CH2:47][CH2:41][C@H:39]([N:36]([CH3:37])[CH3:33])[CH2:40]2)=[C:9]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:10]=1[CH3:21])#[N:20]

Participants

8

Reactant 5

HCID 1049PyridineHCID 6367Acetyl chloride2×HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 510393137-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 68584949HCID 68584949, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrile (#53) (60 mg, 0.16 mmol) was dissolved in tetrahydrofuran (1.2 ml), and with cooling with ice, acetyl chloride (14 μl, 0.19 mmol) and diisopropylethylamine (38 μl, 0.22 mmol) were added, followed by stirring at room temperature for 2 hours. Further, acetyl chloride (14 μl, 0.19 mmol) was added, followed by heating under reflux for 1.5 hours. Since the reaction did not go on, pyridine (1.2 ml) was added, followed by stirring at 90° C. for 15 hours. After cooling followed by fractionation with water and ethyl acetate, the organic layer was washed with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. Elution with a mixed solvent of chloroform/methanol (10:1, v/v) gave the entitled compound (11 g, 0.03 mmol, 17%) as a brown oily substance.

Workup

  1. additionwere added
  2. temperatureby heating
  3. temperatureunder reflux for 1.5 hours
  4. additionwas added
  5. stirringby stirring at 90° C. for 15 hours
  6. temperatureAfter cooling
  7. washthe organic layer was washed with saturated brine
  8. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  9. customthe solvent was evaporated away under reduced pressure
  10. washElution with a mixed solvent of chloroform/methanol (10:1

Sources & evidence

ORD record
ord-1d99e4583e8a49a3bb7bf498a3a58522
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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