Acetic Acid → HCID 67141977, compound

HRID 1932353Notes

Reaction equation

HRID 1932353 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][CH:11]=[C:12]3[CH:16]=[C:15]([CH3:17])[NH:14][C:13]=23)=[CH:4][CH:3]=1.CNC.[C:21]([OH:24])(=O)[CH3:22].[CH2:25]=O>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][CH:11]=[C:12]3[C:16]([CH2:25][O:24][CH2:21][CH3:22])=[C:15]([CH3:17])[NH:14][C:13]=23)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 67141227HCID 67141227, compound

Product 1

HCID 67141977HCID 67141977, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-(4-chlorophenyl)-2-methyl-1H-pyrrolo[2,3-c]pyridine (170 mg, 0.07 mmol) prepared in Example 463, dimethylamine (2.0M tetrahydrofuran solution; 375 μl, 0.75 mmol), acetic acid (0.36 ml) and formaldehyde (0.68 ml) in ethanol (10 ml) was refluxed for 60 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was diluted with a sodium hydroxide solution and then extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5, v/v) to give 85 mg of the titled compound as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe resulting residue was diluted with a sodium hydroxide solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5

Sources & evidence

ORD record
ord-026660c46fc4445f976a3f665e3a482b
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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