1,4-Dioxane → HCID 23114693, compound

HRID 2080465Notes

Reaction equation

HRID 2080465 reaction equation
O1CCOCC1.Cl[C:8]1[CH:13]=[C:12]([CH:14]([S:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])[C:11]([Cl:31])=[CH:10][N:9]=1.[NH2:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1>CCCCCC>[Cl:31][C:11]1[C:12]([CH:14]([S:23][C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])=[CH:13][C:8]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 773174-PyridinemethanamineHCID 231145672,5-Dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine

Product 1

HCID 23114693HCID 23114693, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A dioxane (1.5 ml) solution of the 2,5-dichloro-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridine (229 mg, 0.550 mmol) obtained in Example 54 and 4-aminomethylpyridine (200 μl) was heated at 120° C. for 3 days in a sealed tube. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=1:3 eluate was concentrated under reduced pressure to give the title compound (37 mg, 0.076 mmol, 14%) as an amorphous substance.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue thus obtained
  3. concentrationethyl acetate=1:3 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ea5cfadabdba4a6182f782b1153b5981
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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