Water → 6-chloro-N-[(1S)-1-(3,4-difluorophenyl)ethyl]pyrazin-2-amine

HRID 16142

反応式

HRID 16142 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]([NH2:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[Cl:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15](Cl)[N:14]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[Cl:12][C:13]1[N:14]=[C:15]([NH:11][C@H:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)[CH3:10])[CH:16]=[N:17][CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 785042,6-DichloropyrazineHCID 7016601(S)-1-(3,4-Difluorophenyl)ethanamine

生成物 1

HCID 588699336-chloro-N-[(1S)-1-(3,4-difluorophenyl)ethyl]pyrazin-2-amine収率 35.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

(1S)-1-(3,4-Difluorophenyl)ethanamine (977 mg, 6.2 mmol) and 2,6-dichloropyrazine (1.236 g, 8.3 mmol, 1.3 eq) was dissolved in dioxane (5 mL) and potassium carbonate (1.73 g, 2.0 eq) added to the solution. The mixture was then heated at reflux (110° C.) under a nitrogen atmosphere for 65 hours. The crude reaction mixture was then poured onto cold water (30 mL) and extracted with diethyl ether (3×30 mL). The combined organic extracts were concentrated and subjected to flashmaster chromatography (20 g silica cartridge (8:2 petroleum spirits:ethyl acetate, followed by ethyl acetate flush) to afford the desired pyrazine-adduct as an off-white solid (587 mg, 35%).

後処理

  1. temperatureThe mixture was then heated
  2. customThe crude reaction mixture
  3. extractionextracted with diethyl ether (3×30 mL)
  4. concentrationThe combined organic extracts were concentrated
  5. custom20 g silica cartridge (8:2 petroleum spirits:ethyl acetate, followed by ethyl acetate flush)

出典と根拠

ORDレコード
ord-6509b31877f84ef2b22f7be7512ab378
出典データセット
uspto-grants-2010_06
特許番号
US07737143B2

関連ノート

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