Sodium Carbonate → 2-[4-(3-cyano-2-pyridinyl)-1-piperidinyl]-N-(2,6-dimethylphenyl)acetamide

HRID 490202Notes

Reaction equation

HRID 490202 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]#[N:10])[CH2:3][CH2:2]1.[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1[NH:23][C:24](=[O:27])[CH2:25]Cl.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[C:9]([C:8]1[C:7]([CH:4]2[CH2:3][CH2:2][N:1]([CH2:25][C:24]([NH:23][C:17]3[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:16]=3[CH3:15])=[O:27])[CH2:6][CH2:5]2)=[N:14][CH:13]=[CH:12][CH:11]=1)#[N:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamideHCID 160947122-(Piperidin-4-yl)pyridine-3-carbonitrile

Product 1

HCID 688738942-[4-(3-cyano-2-pyridinyl)-1-piperidinyl]-N-(2,6-dimethylphenyl)acetamideYield 28%

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

The product from Example 58D (trifluoroacetic acid salt, 30 mg, 0.1 mmol), N-(2,6-dimethylphenyl)-2-chloroacetamide (23 mg, 0.15 mmol, Aldrich) and sodium carbonate (50 mg) in N,N-dimethylformamide/water (2:1, 2 mL) was shaken at room temperature for 18 hours. The resulting mixture was decanted, concentrated under reduced pressure. The residue was purified by preparative HPLC to provide 7 mg (28%) of the desired product. 1H NMR (500 MHz, DMSO-d6) δ 1.82 (m, 2H), 2.05 (m, 2H), 2.12 (s, 6H), 2.35 (m, 2H), 3.05 (m, 3H), 3.15 (s, 2H), 7.05 (m, 3H), 7.45 (dd, J=6 Hz, 1H), 8.25 (d, J=6 Hz, 1H), 8.79 (dd, J=6 Hz, 1H), 9.21 (s, 1H); MS (ESI/APCI+) m/e 349 (M+H)+.

Workup

  1. customThe resulting mixture was decanted
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-13bd907a2f56477698c68dc71138aba9
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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