1,4-Dioxane → HCID 59750926, compound

HRID 2080427Notes

Reaction equation

HRID 2080427 reaction equation
O1CCOCC1.C([C:11]1[C:12](Cl)=[N:13][CH:14]=[C:15]([Cl:34])[C:16]=1[CH:17]([S:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[F:25])(C)(C)C.[C:36]([O:40][C:41](=[O:50])[NH:42][CH2:43][CH:44]1[O:49][CH2:48][CH2:47][NH:46][CH2:45]1)([CH3:39])([CH3:38])[CH3:37]>C(OCC)(=O)C>[C:36]([O:40][C:41](=[O:50])[NH:42][CH2:43][CH:44]1[O:49][CH2:48][CH2:47][N:46]([C:12]2[CH:11]=[C:16]([CH:17]([S:26][C:27]3[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=3)[C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[C:15]([Cl:34])=[CH:14][N:13]=2)[CH2:45]1)([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 19081107tert-Butyl [(morpholin-2-yl)methyl]carbamateHCID 23114745HCID 23114745, compound

Product 1

HCID 59750926HCID 59750926, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 1,4-dioxane (1.0 ml) solution of the t-butyl 2,5-dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (60 mg, 0.14 mmol) obtained in Example 54 and t-butyl(morpholin-2-yl)methylcarbamate (200 mg) was stirred at 100° C. for 2 days under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (50 ml). The diluted mixture was washed with water and brine, dried and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ether=5:1) to give the title compound (45 mg, 52%) as an oil.

Workup

  1. washThe diluted mixture 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 (hexane:ether=5:1)

Sources & evidence

ORD record
ord-cf347a6d0ca647b8903a9a635345777e
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

Loading…