Benzoyl chloride → HCID 11067619, compound

HRID 581249Notes

Reaction equation

HRID 581249 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1.[OH-].[Na+].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[C:20]([NH:1][C:2]1[N:7]=[C:6]2[C:8]([CH:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 102202303-(1-Methyl-piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-ylamine

Product 1

HCID 11067619HCID 11067619, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.100 gm (0.43 mMol) 5-amino-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine in 3 mL 50% aqueous tetrahydrofuran were added 0.43 mL (0.86 mMol) 2N sodium hydroxide followed by 0.065 mL (0.56 mMol) benzoyl chloride and the resulting mixture was stirred at room temperature. After about 4 hours the reaction mixture was partitioned between dichloromethane and 2N sodium hydroxide. The phases were separated and the aqueous phase extracted well with dichloromethane. The organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with a gradient of dichloromethane (2-10% methanol) containing 1% ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure to provide 0.095 gm (66%) of the title compound. A portion was recrystallized from ethanol/water to provide an analytical sample.

Workup

  1. customAfter about 4 hours the reaction mixture was partitioned between dichloromethane and 2N sodium hydroxide
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted well with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with a gradient of dichloromethane (2-10% methanol)
  7. additioncontaining 1% ammonium hydroxide
  8. additionFractions containing product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-51f0fa25aaa24a46a847640a9ee963be
Source dataset
uspto-grants-1999_07
Patent number
US05919936

Reaction notes

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