2-Morpholinoethylamine → HCID 23114883, compound

HRID 748842Notes

Reaction equation

HRID 748842 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]([S:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[F:16])[C:5]([Cl:25])=[CH:4][N:3]=1.[NH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>O1CCOCC1.C(OCC)(=O)C>[Cl:25][C:5]1[C:6]([CH:8]([S:17][C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[F:16])=[CH:7][C:2]([NH:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 231145672,5-Dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine

Product 1

HCID 23114883HCID 23114883, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Under nitrogen atmosphere, a solution of the 2,5-dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (100 mg, 0.24 mmol) obtained in Example 342 and 4-(2-aminoethyl)morpholine (200 μl) in 1,4-dioxane (1.0 ml) was stirred at 100° C. for 2 days. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (40 ml). The solution was washed with water and brine, dried and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (3% methanol/chloroform), whereby the title compound (12 mg, 10%) was obtained as an oil.

Workup

  1. washThe solution was washed with water and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel chromatography (3% methanol/chloroform), whereby the title compound (12 mg, 10%)
  6. customwas obtained as an oil

Sources & evidence

ORD record
ord-260d8138476b4b2bab9fb30b9da46a48
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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