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

HRID 1827691Notes

Reaction equation

HRID 1827691 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 5-7 (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 5-8 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-2e31b71ec59045cf9f183f55d502bf7c
Source dataset
uspto-grants-2006_06
Patent number
US07056909B2

Reaction notes

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