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

HRID 1959368노트

반응식

HRID 1959368 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-95b8c108bda14ba7b48eb0e630a64324
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410112B2

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