Methylamine → HCID 53888460, compound

HRID 2293477Notes

Reaction equation

HRID 2293477 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][NH2:28]>>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:4]2[N:3]=[C:2]([NH:28][CH3:27])[C:7]([C:8]#[N:9])=[CH:6][C:5]=2[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 6329Methylamine2×HCID 53669110HCID 53669110, compound

Product 1

HCID 53888460HCID 53888460, compound

Conditions

Temperature
70 °C

Procedure

2-Chloro-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyridine-3-carbonitrile (Example 7) (200 mg, 0.52 mMol) was charged with methylamine. The solution was shaken for 24 hours at 70° C. and 74 psi by a Parr Shaker. The vessel was cooled to room temperature and vented to allow excess methylamine to evaporate leaving a yellow solid. The solid was washed with methyl alcohol and recrystallized from chloroform: m.p. (DSC): 295.63° C. Anal. Calc'd. for C20H16N3O2SF (381.43): C, 62.98; H, 4.23; N, 11.02. Found: C, 62.59; H, 4.15; N, 10.77.

Workup

  1. temperatureThe vessel was cooled to room temperature
  2. customto evaporate
  3. customleaving a yellow solid
  4. washThe solid was washed with methyl alcohol
  5. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-ea8afbef41dd4bdd9937b234cde26341
Source dataset
uspto-grants-1997_11
Patent number
US05686470

Reaction notes

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