Water → HCID 118558060, compound

HRID 2207237Notes

Reaction equation

HRID 2207237 reaction equation
[Br-].[C:2]([C:5]1[CH:6]=[N+:7]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH:8]=[CH:9][C:10]=1[CH2:11][CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[C:13]1=[O:24])(=[O:4])[CH3:3].C(NC(=O)C1CC=CNC=1)C1C=CC=CC=1.O>ClCCl>[C:2]([C:5]1[CH:10]([CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[C:13]2=[O:24])[CH:9]=[CH:8][N:7]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH:6]=1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 15042636N-Benzyl-1,4-dihydropyridine-3-carboxamideHCID 118557818HCID 118557818, compound

Product 1

HCID 118558060HCID 118558060, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of pyridinium salt 131 (75 mg, 0.15 mmol) in dry and degassed dichloromethane (2.5 mL) was added at once N-benzyl-1,4-dihydronicotinamide (BNAH) (32 mg, 1 equiv) at 25° C. under Argon. The reaction was monitored by TLC until the starting material has disappeared (48 h). Then, water and dichloromethane were added. The organic layer was washed twice with water and once with brine, dried over magnesium sulfate and concentrated to dryness. The crude residue was purified by column chromatography (gradient of EtOAc in petroleum ether) to afford the title compound 153 as a yellow solid (Yield 29 mg, 44%).

Workup

  1. customdegassed dichloromethane (2.5 mL)
  2. custom(48 h)
  3. washThe organic layer was washed twice with water and once with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crude residue was purified by column chromatography (gradient of EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-6e035ba1cb94453c9b46675763ad062d
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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