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

HRID 2080534ノート

反応式

HRID 2080534 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ebadd8740dcd446dab2bdb5309cf3e9c
出典データセット
uspto-grants-2011_04
特許番号
US07932271B2

反応ノート

読み込み中…