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Triethylamine → HCID 66744626, 화합물

HRID 1959365
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HRID 1959365 반응식
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[C:7]1([C:13]2[O:17][C:16]([C:18]3[C:19]([NH2:30])=[N:20][CH:21]=[C:22]([N:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)[N:23]=3)=[N:15][N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([S:3]([N:27]1[CH2:28][CH2:29][N:24]([C:22]2[N:23]=[C:18]([C:16]3[O:17][C:13]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[N:14][N:15]=3)[C:19]([NH2:30])=[N:20][CH:21]=2)[CH2:25][CH2:26]1)(=[O:5])=[O:4])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

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HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 667444203-(5-Phenyl-1,3,4-oxadiazol-2-yl)-5-(piperazin-1-yl)pyrazin-2-amine

생성물 1

HCID 66744626HCID 66744626, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Ethanesulfonyl chloride (37.51 mg, 27.64 μL, 0.2917 mmol) was added to a solution of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-piperazin-1-yl-pyrazin-2-amine (116 mg, 0.2652 mmol) and triethylamine (53.67 mg, 73.93 μL, 0.5304 mmol) in dichloromethane (5 mL) at 0° C. and the resulting solution stirred at room temperature for 1.5 hours. The mixture was diluted with dichloromethane, washed with water and the aqueous layer extracted further with dichloromethane. The organics were washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel by flash column chromatography (3% MeOH/DCM) to afford the title compound still impure. This was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound (25.2 mg, 18% Yield).

후처리

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

출처 및 근거

ORD 기록
ord-6923a81db72d4a1fa22eb05ba4e92317
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410112B2

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