Sodium Carbonate → N-(6-(6-(N,4-dimethylphenylsulfonamido)pyridin-2-yl)benzo[d]thiazol-2-yl)acetamide

HRID 2077505노트

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HRID 2077505 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:19])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:40]=[CH:39][C:31]3[N:32]=[C:33]([NH:35][C:36](=[O:38])[CH3:37])[S:34][C:30]=3[CH:29]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C(Cl)Cl.C([O-])(O)=O.[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][N:8]([C:6]1[N:7]=[C:2]([C:28]2[CH:40]=[CH:39][C:31]3[N:32]=[C:33]([NH:35][C:36](=[O:38])[CH3:37])[S:34][C:30]=3[CH:29]=2)[CH:3]=[CH:4][CH:5]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 51354026n-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamideHCID 57585115N-(6-chloropyridin-2-yl)-N,4-dimethylbenzenesulfonamide

생성물 1

HCID 25183328N-(6-(6-(N,4-dimethylphenylsulfonamido)pyridin-2-yl)benzo[d]thiazol-2-yl)acetamide

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매HCID 516892Sodium Bicarbonate용매

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온도
95 °C

실험 절차

N-(6-Chloropyridin-2-yl)-N,4-dimethylbenzenesulfonamide (0.080 g, 0.27 mmol) was dissolved in 1,4-dioxane (6 mL), and N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.1 g, 0.3 mmol), tetrakis(triphenylphosphine)palladium (0) (0.04 g, 0.04 mmol) and 2M Na2CO3 (0.3 mL, 0.6 mmol) were added to the mixture. The flask was fit with a reflux condensor and placed into a pre-heated (95° C.) bath and stirred under an inert atmosphere overnight. The mixture was then allowed to cool to ambient temperature and diluted with DCM and saturated NaHCO3. The organic layers were collected by extracting with DCM three times, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude was purified by silica gel chromatography (1-10% IPA/DCM) to give N-(6-(6-(N,4-dimethylphenylsulfonamido)pyridin-2-yl)benzo[d]thiazol-2-yl)acetamide as a tan solid. MS (ESI pos. ion) m/z: 453 (MH+). Calculated exact mass for C22H20N4O3S2: 452. 1H NMR (400 MHz, DMSO-d6): 8.35 (s, 1H), 7.93 (t, J=8.0 Hz, 2H), 7.83 (d, J=7.5 Hz, 1H), 7.74 (d, J=8.5 Hz, 1H), 7.58 (d, J=8.0 Hz, 2H), 7.48 (d, J=8.0 Hz, 1H), 7.37 (d, J=7.5 Hz, 2H), 3.38 (s, 3H), 2.36 (s, 3H), 2.22 (s, 3H).

후처리

  1. temperatureto cool to ambient temperature
  2. customThe organic layers were collected
  3. extractionby extracting with DCM three times
  4. dry with materialthe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by silica gel chromatography (1-10% IPA/DCM)

출처 및 근거

ORD 기록
ord-c907512aaa2340da879f3b87e392bf63
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928140B2

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