Dimethylamine → HCID 53940149, compound

HRID 2293475Notes

Reaction equation

HRID 2293475 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[N:3]=1.[CH3:27][NH:28][CH3:29]>C(O)C>[CH3:27][N:28]([CH3:29])[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=2)=[C:4]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[N:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 53669110HCID 53669110, compound

Product 1

HCID 53940149HCID 53940149, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

2-Chloro-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyridine-3-carbonitrile (Example 7) (200 mg, 0.52 mMol) in ethanol (150 ml) was charged with dimethylamine. The solution was shaken for 24 hours at 70° C. and a pressure of 22 psi in a Parr shaker. The solution was concentrated. The residue was titurated with methyl alcohol and filtered to give a yellow solid: m.p. (DSC): 205.02° C. Anal. Calc'd. for C21H18 N3O2SF (395.46): C, 63.78; H, 4.59; N, 10.63. Found: C, 64.02; H, 4.58; N, 10.77.

Workup

  1. concentrationThe solution was concentrated
  2. filtrationfiltered
  3. customto give a yellow solid

Sources & evidence

ORD record
ord-bce8c57bbc5146eaa70bc54bdab01c2f
Source dataset
uspto-grants-1997_11
Patent number
US05686470

Reaction notes

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