Water → HCID 66692117, compound

HRID 710559Notes

Reaction equation

HRID 710559 reaction equation
BrCC1C=C(C=CC=1)[C:6]#[N:7].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[CH:19]=[C:20]([CH:46]=[CH:47][C:48]=1OC)[CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([NH:28][C:29]([N:31]2[CH2:36][CH2:35][C:34](=[CH:37][C:38]3[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:39]=3[F:45])[CH2:33][CH2:32]2)=[O:30])[CH2:24][CH2:23]1.O>CN(C=O)C>[C:6]([C:18]1[CH:19]=[C:20]([CH:46]=[CH:47][CH:48]=1)[CH2:21][N:22]1[CH2:23][CH2:24][CH:25]([NH:28][C:29]([N:31]2[CH2:36][CH2:35][C:34](=[CH:37][C:38]3[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:39]=3[F:45])[CH2:33][CH2:32]2)=[O:30])[CH2:26][CH2:27]1)#[N:7]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 66691939HCID 66691939, compound

Product 1

HCID 66692117HCID 66692117, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromomethylbenzonitrile (160 mg, 0.81 mmol) was dissolved in DMF (3.0 mL), and potassium carbonate (220 mg, 1.62 mmol) and the compound (300 mg, 0.81 mmol) obtained in Example 36 (1) were added thereto, followed by stirring overnight while heating at room temperature. Water was added to the reaction mixture, and after extraction with chloroform, the extract was washed with water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporation under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:200), thereby giving the title compound (151 mg, 42%) as a white solid.

Workup

  1. extractionafter extraction with chloroform
  2. washthe extract was washed with water
  3. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  4. filtrationAfter the desiccant was filtered off
  5. customthe residue obtained by evaporation under reduced pressure
  6. customwas purified

Sources & evidence

ORD record
ord-f4a8e98e85664bbeb05443884dffe995
Source dataset
uspto-grants-2015_11
Patent number
US09181183B2

Reaction notes

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