Nitrogen → 2-Chloro-6-(1,1-dioxo-1lambda~6~,4-thiazinan-4-yl)-4-(4-fluoro-2-methylphenyl)pyridine-3-carbonitrile

HRID 131110Notes

Reaction equation

HRID 131110 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[Cl:7][C:8]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[CH3:23])[CH:11]=[C:10]([N:24]2[CH2:29][CH2:28]S[CH2:26][CH2:25]2)[N:9]=1.N#N>CN1C(=O)CCC1.O>[Cl:7][C:8]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[CH3:23])[CH:11]=[C:10]([N:24]2[CH2:25][CH2:26][S:3](=[O:5])(=[O:2])[CH2:28][CH2:29]2)[N:9]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 23707502Potassium hydroxy sulfiteHCID 573550072-Chloro-4-(4-fluoro-2-methylphenyl)-6-(thiomorpholin-4-yl)pyridine-3-carbonitrile

Product 1

HCID 573550082-Chloro-6-(1,1-dioxo-1lambda~6~,4-thiazinan-4-yl)-4-(4-fluoro-2-methylphenyl)pyridine-3-carbonitrileYield 101.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
25 °C

Procedure

Oxone® (56.18 g, 91.4 mmol) was added to a solution of 2-chloro-3-cyano-4-(4-fluoro-2-methylphenyl)-6-(thiomorpholino)pyridine (26.54 g, 76.3 mmol) in 200 mL of NMP in a 1000-mL, 3-necked flask (equipped with a teflon paddle stirrer, septum with teflon-coated thermocouple, dry N2 adapter). The mixture was stirred at 25° C. for 20 hours, and diluted with 800 mL of water. The resulting mixture was stirred at 25° C. for 30 minutes. The precipitate was filtered, washed several times with H2O, and dried to afford 29.30 g (101.1%) of 2-chloro-3-cyano-4-(4-fluoro-2-methylphenyl)-6-(1,1-dioxo-thiomorpholin-4-yl)pyridine as a colorless solid.

Workup

  1. stirringThe resulting mixture was stirred at 25° C. for 30 minutes
  2. filtrationThe precipitate was filtered
  3. washwashed several times with H2O
  4. customdried

Sources & evidence

ORD record
ord-11bda2e93f4448a79f607231dd48d592
Source dataset
uspto-grants-2008_06
Patent number
US07384939B2

Reaction notes

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