Formamide → (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(dimethylamino)-6-methoxypyridin-2-yl]ethenyl}pyrrolidin-2-one

HRID 70649Notes

Reaction equation

HRID 70649 reaction equation
[CH:1]([NH2:3])=O.N[C:5]1[CH:6]=[CH:7][C:8](/[C:13](/[C:21]2[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=2)=[CH:14]/[C@@H:15]2[NH:19]C(=O)C[CH2:16]2)=[N:9][C:10]=1OC.C(O[BH-](O[C:41](=[O:43])[CH3:42])OC(=O)C)(=O)C.[Na+].[C:45](=[O:48])(O)[O-].[Na+].[C:50](#N)C>>[C:27]([C:24]1[CH:25]=[CH:26][C:21](/[C:13](/[C:8]2[CH:7]=[CH:6][C:5]([N:3]([CH3:1])[CH3:50])=[C:10]([O:48][CH3:45])[N:9]=2)=[CH:14]\[C@@H:15]2[NH:19][C:41](=[O:43])[CH2:42][CH2:16]2)=[CH:22][CH:23]=1)([CH3:28])([CH3:29])[CH3:30]

Participants

6

Reactant 5

HCID 713FormamideHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67399550HCID 67399550, compound

Product 1

HCID 67400002(5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(dimethylamino)-6-methoxypyridin-2-yl]ethenyl}pyrrolidin-2-one

Procedure

A 37% formamide solution (40 μL) was added to a solution of (5R)-5-[(E)-2-(5-amino-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one obtained in Example 4-173(2) (40 mg) in acetonitrile (2 mL) under ice-cooling, followed by stirring for 10 minutes. Sodium triacetoxyborohydride (120 mg) was added thereto and the mixture was stirred at room temperature for 15 hours. Saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure to give (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(dimethylamino)-6-methoxypyridin-2-yl]ethenyl}pyrrolidin-2-one as a yellow oil (41 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 15 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customafter which the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-237b59d9315147ae833ae00b60489882
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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