Triethylamine → 5-(1-(Ethylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine

HRID 1959368ノート

反応式

HRID 1959368 の反応式
[C:1]1([C:7]2[O:11][C:10]([C:12]3[C:13]([NH2:24])=[N:14][CH:15]=[C:16]([C:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH:23]=4)[N:17]=3)=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[CH2:32]([S:34](Cl)(=[O:36])=[O:35])[CH3:33]>C(Cl)Cl>[CH2:32]([S:34]([N:21]1[CH2:20][CH:19]=[C:18]([C:16]2[N:17]=[C:12]([C:10]3[O:11][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:8][N:9]=3)[C:13]([NH2:24])=[N:14][CH:15]=2)[CH2:23][CH2:22]1)(=[O:36])=[O:35])[CH3:33]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 461995573-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

生成物 1

HCID 667450735-(1-(Ethylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine (50 mg, 0.1151 mmol) was dissolved in DCM (3 mL) and Et3N (34.94 mg, 48.13 μL, 0.3453 mmol) followed by ethanesulfonyl chloride (16.28 mg, 12.00 μL, 0.1266 mmol) were added. The reaction was allowed to stir for 30 mins and then diluted with dichloromethane and washed with water. The aqueous layer was extracted further with dichloromethane and the organics washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel by flash column chromatography (0-5% MeOH/DCM) to afford the title compound (47.47 mg, 60% Yield).

後処理

  1. additionwere added
  2. washwashed with water
  3. extractionThe aqueous layer was extracted further with dichloromethane
  4. washthe organics washed with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified on silica gel by flash column chromatography (0-5% MeOH/DCM)

出典と根拠

ORDレコード
ord-95b8c108bda14ba7b48eb0e630a64324
出典データセット
uspto-grants-2013_04
特許番号
US08410112B2

反応ノート

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