Triethylamine → 5-Chloro-2-imino-1-[3-(methylsulfinyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 447804ノート

反応式

HRID 447804 の反応式
[C:1]([CH:3]([CH:7]1[C:11]([Cl:12])=[C:10](Cl)C(=O)O1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[CH3:16][S:17]([C:19]1[CH:20]=[C:21]([CH2:25][NH2:26])[CH:22]=[CH:23][CH:24]=1)=[O:18].C(N(CC)CC)C>CO>[ClH:12].[Cl:12][C:11]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:1](=[NH:2])[N:26]([CH2:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([S:17]([CH3:16])=[O:18])[CH:20]=2)[CH:10]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 5417922-Cyano-2-(3,4-dichloro-5(2H)-oxo-2-furyl)acetamideHCID 668784001-[3-(Methylsulfinyl)phenyl]methanamine hydrochloride

生成物 1

HCID 669697955-Chloro-2-imino-1-[3-(methylsulfinyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrochloride収率 35.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
50 °C

実験手順

To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (1.0 g) in methanol (10 ml) was added a solution of 1-[3-(methylsulfinyl)phenyl]methanamine hydrochloride (1.8 g) and triethylamine (2.4 ml) in methanol (5 ml) at room temperature, and the mixture was stirred overnight at 50° C. The reaction solvent was evaporated under reduced pressure, acetic acid (5 ml) was added, and the mixture was stirred at 50° C. for 2 hr. The solvent was evaporated under reduced pressure, the residue was partitioned with ethyl acetate, 1N aqueous sodium hydroxide solution and aqueous sodium bicarbonate, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (270 mg).

後処理

  1. customThe reaction solvent was evaporated under reduced pressure, acetic acid (5 ml)
  2. additionwas added
  3. stirringthe mixture was stirred at 50° C. for 2 hr
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was partitioned with ethyl acetate, 1N aqueous sodium hydroxide solution and aqueous sodium bicarbonate
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0)
  9. addition4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil
  10. filtrationthe precipitated crystals were collected by filtration
  11. customrecrystallized

出典と根拠

ORDレコード
ord-645ba1f41fc24befbe3ea0303e873081
出典データセット
uspto-grants-2013_07
特許番号
US08481569B2

反応ノート

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