Diisopropylethylamine → 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)-N-phenacyl-pyrazine-2-carboxamide

HRID 1959393

반응식

HRID 1959393 반응식
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[NH2:12][C:13]1[C:14]([C:30](O)=[O:31])=[N:15][C:16]([N:19]2[CH2:24][CH2:23][N:22]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])[CH2:21][CH2:20]2)=[CH:17][N:18]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.CCOC(C)=O.O>[NH2:12][C:13]1[C:14]([C:30]([NH:2][CH2:3][C:4](=[O:5])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:31])=[N:15][C:16]([N:19]2[CH2:20][CH2:21][N:22]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])[CH2:23][CH2:24]2)=[CH:17][N:18]=1

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 667445273-Amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazine-2-carboxylic acid

생성물 1

HCID 667454513-amino-6-(4-ethylsulfonylpiperazin-1-yl)-N-phenacyl-pyrazine-2-carboxamide수율 67%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 22728543Water ethylacetate용매

실험 절차

2-amino-1-phenyl-ethanone hydrochloride (136.1 mg, 0.7928 mmol) was added to a solution of 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)pyrazine-2-carboxylic acid (250 mg, 0.7928 mmol) and DIPEA (512.3 mg, 690.4 μL, 3.964 mmol) in CH2Cl2 (3.332 mL) and DMF (833.2 μL) and the resulting solution stirred at room temperature for 1 hour. The reaction was diluted with EtOAc/water and the layers separated. The aqueous layer was extracted further with EtOAc (2×) and the combined organics washed with water (3×), dried (MgSO4) and concentrated in vacuo. The mixture was purified on silica gel by flash column chromatography (100% EtOAc) to afford the product (229 mg, 67% Yield). 1H NMR (CDCl3) d 1.28 (3H, t), 3.06 (2H, q), 3.51-3.53 (4H, m), 3.56-3.59 (4H, m), 4.95 (2H, d), 6.2 (2H, br s), 7.56 (2H, m), 7.68 (1H, m), 8.05 (3H, m), 8.65 (1H, m) ppm; MS (ES+) 433.0

후처리

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted further with EtOAc (2×)
  3. washthe combined organics washed with water (3×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe mixture was purified on silica gel by flash column chromatography (100% EtOAc)

출처 및 근거

ORD 기록
ord-1359dd61b4354e79adf8a7df2f1491e3
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410112B2

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