Water → HCID 68808274, compound

HRID 1455530Notes

Reaction equation

HRID 1455530 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](=[O:9])[N:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4]=1[S-:16])#[N:2].[Na+].[OH2:18].[CH3:19][C:20]#[N:21]>>[O:9]=[C:6]1[N:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4]([S:16][CH2:19][C:20](=[O:18])[N:21]2[CH2:7][CH2:8][CH2:3][CH2:1]2)=[C:3]([C:1]#[N:2])[CH:8]=[CH:7]1

Participants

4

Reactant 3

HCID 962WaterHCID 6342AcetonitrileHCID 11615758Sodium 3-cyano-6-oxo-1-phenyl-1,6-dihydropyridine-2-thiolate

Product 1

HCID 68808274HCID 68808274, compound

Procedure

A mixture of Example 1 (0.5 g) and Intermediate 2 (0.35 g) in MeCN (10 mL) was heated at reflux for 1.5 h. H2O (2.5 mL) was added and the resulting mixture was concentrated in vacuo. The resulting solid precipitate was recovered by filtration and dried under vacuum to give 6-oxo-2-[2-oxo-2-(pyrrolidin-1-yl)ethylsulfanyl]-1-phenyl-1,6-dihydropyridine-3-carbonitrile (0.56 g). δH (DMSO-d6) 7.998 (1H, d, J 9.5 Hz), 7.75 (3H, m), 7.55 (2H, m), 6.85 (1H, d, J 9.5 Hz), 3.86 (2H, s), 3.62-3.37 (4H, m), 2.15-1.90 (4H, m). A mixture of this material (0.38 g) and K2CO3 (0.31 g) in EtOH (7.5 mL) was heated at reflux for 2.5 h. H2O (10 mL) was added and the mixture was concentrated under vacuum. The resulting solid product was filtered, washed with water and dried in vacuo to give the title compound as an off-white solid (0.37 g). δH (DMSO-d6) 8.12 (1H, d, J 9.4 Hz), 7.66-7.50 (3H, m), 7.44 (2H, m), 7.25 (2H, br s), 6.50 (1H, d, J 9.4 Hz), 3.36 (4H, m), 1.75 (4H, m). LCMS (ES+) RT 2.84 minutes, 340 (M+H)+.

Workup

  1. temperatureat reflux for 1.5 h
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. filtrationThe resulting solid precipitate was recovered by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2ee1d6d7c8e744f387b7fe51768a23ea
Source dataset
uspto-grants-2009_01
Patent number
US07482452B2

Reaction notes

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