Acetonitrile → cis-{1-isopropyl-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidin-4-yl}-carbamic acid benzyl ester

HRID 1271716Notes

Reaction equation

HRID 1271716 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[NH:10][C@H:11]1[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]1[NH:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]2=[O:31])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34]([O-])([O-])=O.[Na+].[Na+].[CH3:40][C:41]#N>>[CH2:1]([O:8][C:9](=[O:33])[NH:10][C@H:11]1[CH2:16][CH2:15][N:14]([CH:41]([CH3:40])[CH3:34])[CH2:13][C@H:12]1[NH:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]2=[O:31])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 69146550HCID 69146550, compound

Product 1

HCID 69146647cis-{1-isopropyl-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidin-4-yl}-carbamic acid benzyl ester

Conditions

Temperature
80 °C

Procedure

Cis-{3-[4-(2-Oxo-2H-pyridin-1-yl)-benzoylamino]-piperidin-4-yl}-carbamic acid benzyl ester (0.26 mmol) was dissolved in CH3CN (1.5 ml). Iodoisopropane (0.04 mL) was added, followed by the addition of Na2CO3 (70 mg). The resulting mixture was stirred at 80° C. overnight. After cooling, it was extracted with EtOAc (3×), dried over MgSO4, filtered, and concentrated to dryness to give crude cis-{1-isopropyl-3-[4-(2-oxo-2H-pyridin-1-yl)-benzoylamino]-piperidin-4-yl}-carbamic acid benzyl ester (115 mg).

Workup

  1. temperatureAfter cooling
  2. extractionit was extracted with EtOAc (3×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-eeb5565acce841e1b7a3dc7f7dab5c53
Source dataset
uspto-grants-2007_04
Patent number
US07205318B2

Reaction notes

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