Hexane → 5-Chloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]pyridin-2-ylamine

HRID 2080535ノート

反応式

HRID 2080535 の反応式
[Cl:1][C:2]1[C:3]([CH:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])=[CH:4][C:5]([NH:8]CC2C=CC(OC)=C(OC)C=2)=[N:6][CH:7]=1.C(=O)(O)[O-].[Na+].CCCCCC>FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:3]([CH:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 8058HexaneHCID 516892Sodium BicarbonateHCID 231145495-Chloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine

生成物 1

HCID 587342705-Chloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]pyridin-2-ylamine収率 68%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
65 °C

実験手順

The 5-chloro-4-[(4-chlorophenylsulfonyl)(2,6-difluorophenyl)methyl]-2-(3,4-dimethoxybenzylamino)pyridine (293 mg, 0.506 mmol) obtained in Example 295 was dissolved in trifluoroacetic acid (4 ml). The resulting solution was heated at 65° C. for 2 hours. The reaction mixture was concentrated. The residue thus obtained was basified with a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The extract was washed with 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. The solid thus obtained was recrystallized from ethyl acetate-hexane to give the title compound (147 mg, 0.343 mmol, 68%) as a white solid.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue thus obtained
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. concentrationethyl acetate=2:1 eluate was concentrated
  9. customThe solid thus obtained
  10. customwas recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-4c3fd390384b4e24b72f2d87b8270fa0
出典データセット
uspto-grants-2011_04
特許番号
US07932271B2

反応ノート

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