Hexane → 5-Chloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine

HRID 2080534Notes

Reaction equation

HRID 2080534 reaction equation
CN1CCCC1=O.Cl[C:9]1[CH:14]=[C:13]([CH:15]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])[C:12]([Cl:34])=[CH:11][N:10]=1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:40][NH2:41].CCCCCC>C(OCC)(=O)C>[Cl:34][C:12]1[C:13]([CH:15]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)(=[O:26])=[O:25])[C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])=[CH:14][C:9]([NH:41][CH2:40][C:39]2[CH:42]=[CH:43][C:44]([O:45][CH3:46])=[C:37]([O:36][CH3:35])[CH:38]=2)=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 13387N-methyl-2-pyrrolidoneHCID 79832VeratrylamineHCID 231146812,5-Dichloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]pyridine

Product 1

HCID 231145495-Chloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridineYield 30.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To an N-methyl-2-pyrrolidone solution (20 ml) of the 2,5-dichloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]pyridine (755 mg, 1.68 mmol) obtained in Example 294 was added 3,4-dimethoxybenzylamine (0.745 ml, 5.04 mmol) under an argon atmosphere. The resulting mixture was heated at 150° C. for 5 hours. The reaction mixture was returned to room temperature and then, diluted with ethyl acetate. The diluted solution was washed with a saturated aqueous solution of ammonium chloride, a saturated aqueous solution of sodium bicarbonate, water and brine, dried over magnesium sulfate, and concentrated. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated to give the title compound (295 mg, 0.509 mmol, 30%) as a white amorphous substance.

Workup

  1. customwas returned to room temperature
  2. washThe diluted solution was washed with a saturated aqueous solution of ammonium chloride
  3. dry with materiala saturated aqueous solution of sodium bicarbonate, water and brine, dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue thus obtained
  6. concentrationethyl acetate=2:1 eluate was concentrated

Sources & evidence

ORD record
ord-ebadd8740dcd446dab2bdb5309cf3e9c
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

Loading…