Sodium hydride → 5-(6,7,8,9-Tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-pentanoic acid methylamide

HRID 2187386Notes

Reaction equation

HRID 2187386 reaction equation
[CH3:1][NH:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])=[CH:10][N:9]=1.[H-].[Na+]>>[CH3:1][NH:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]2[CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:10]=2[N:9]=1

Participants

3

Reactant 2

HCID 24758Sodium hydrideHCID 220826725-[5-(4-Aminobutyl)pyridin-2-YL]-N-methylpentanamide

Product 1

HCID 220826735-(6,7,8,9-Tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-pentanoic acid methylamide

Procedure

A mixture of 11-7 (24 g, 91.2 mmol) and NaH (10.9 g of a 60% weight dispersion in mineral oil, 273 mmol) in xylenes (500 mL) was purged with argon for 30 min, and then heated at reflux for 72 hours. The mixture was cooled, quenched with ethanol, diluted with 10% aqueous potassium carbonate and extracted with ethyl acetate. The organics were dried over MgSO4, and concentrated to an oil. The residue was chromatographed on silica gel (70:25:5 CHCl3/EtOAc/MeOH/H2O) to give 11-8 as a white solid.

Workup

  1. customwas purged with argon for 30 min
  2. temperatureheated
  3. temperatureat reflux for 72 hours
  4. temperatureThe mixture was cooled
  5. customquenched with ethanol
  6. additiondiluted with 10% aqueous potassium carbonate
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organics were dried over MgSO4
  9. concentrationconcentrated to an oil
  10. customThe residue was chromatographed on silica gel (70:25:5 CHCl3/EtOAc/MeOH/H2O)

Sources & evidence

ORD record
ord-9fe5baa1f4e44925b48ac668b03ff758
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

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