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

HRID 16142

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HRID 16142 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

(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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-6509b31877f84ef2b22f7be7512ab378
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737143B2

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