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Dichloromethane → 3-[5-Amino-6-(pyridine-3-carbonyl)-pyrazin-2-yl]-N-(2-methoxy-ethyl)-benzenesulfonamide

HRID 2387190
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HRID 2387190 반응식
[NH2:1][C:2]1[C:3]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C(Cl)Cl.C([O-])(=O)C.[K+].Br[C:44]1[CH:45]=[C:46]([S:50]([NH:53][CH2:54][CH2:55][O:56][CH3:57])(=[O:52])=[O:51])[CH:47]=[CH:48][CH:49]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:44]2[CH:45]=[C:46]([S:50]([NH:53][CH2:54][CH2:55][O:56][CH3:57])(=[O:51])=[O:52])[CH:47]=[CH:48][CH:49]=2)=[N:4][C:3]=1[C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 6

HCID 6344Dichloromethane2회HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 471084603-Bromo-n-(2-methoxyethyl)benzenesulfonamideHCID 86634541(3-Amino-6-bromo-pyrazin-2-yl)-pyridin-3-yl-methanone

생성물 1

HCID 44233103
3-[5-Amino-6-(pyridine-3-carbonyl)-pyrazin-2-yl]-N-(2-methoxy-ethyl)-benzenesulfonamide

시약·촉매·용매 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매2회HCID 80711,2-Dimethoxyethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

A suspension of (3-Amino-6-bromo-pyrazin-2-yl)-pyridin-3-yl-methanone (Intermediate AA) (0.05 g, 0.18 mmol), bis(pinacolato)diboron (0.05 g, 0.19 mmol), Pd(dppf)Cl2.DCM (0.015 g, 0.018 mmol) and potassium acetate (0.03 g, 0.27 mmol) in DME (4 ml) is heated at reflux for 4 hours. Pd(dppf)Cl2.DCM (7 mg, 0.009 mmol), 3-Bromo-N-(2-methoxy-ethyl)-benzenesulfonamide (Intermediate DD) (0.05 g, 0.18 mmol), 2M Na2CO3 (1 ml) and DME (3 ml) are added to the suspension, which is heated at reflux for a further 1 hour. After cooling, the reaction mixture is diluted with EtOAc, washed with water, dried (MgSO4) and filtered through a short pad of Celite® (filter material). The solvent is removed in vacuo, and the residue purified by flash column chromatography (SiO2, iso-hexane/EtOAc) to afford the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.16 (2H, m), 8.86 (1H, dd), 8.43 (1H, dt), 8.37 (1H, m), 8.23 (3H, m), 7.85 (1H, m), 7.77 (1H, m), 7.66 (1H, ddd), 3.38 (2H, t), 3.22 (3H, s), 3.01 (2H, m). MS m/z 414.01 [M+H]+

후처리

  1. temperatureat reflux for 4 hours
  2. temperatureis heated
  3. temperatureat reflux for a further 1 hour
  4. temperatureAfter cooling
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered through a short pad of Celite® (filter material)
  8. customThe solvent is removed in vacuo
  9. customthe residue purified by flash column chromatography (SiO2, iso-hexane/EtOAc)

출처 및 근거

ORD 기록
ord-e0f0653bc55b45e89dc94a7ee9d9e7ce
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08268834B2

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