1-(7-Bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea → 1-[7-(6-Dimethylamino-pyridin-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-3-ethyl-urea

HRID 447043노트

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HRID 447043 반응식
Br[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:3]=1.[CH3:23][N:24]([CH3:44])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Sn](CCCC)(CCCC)CCCC)[N:26]=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:23][N:24]([CH3:44])[C:25]1[N:26]=[C:27]([C:2]2[C:10]3[S:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:7][C:6]=3[CH:5]=[C:4]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:3]=2)[CH:28]=[CH:29][CH:30]=1

참가 물질

5

반응물 2

HCID 248642171-(7-Bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-ureaHCID 57813708N,N-Dimethyl-6-(tributylstannyl)pyridin-2-amine

생성물 1

HCID 578136001-[7-(6-Dimethylamino-pyridin-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-3-ethyl-urea수율 5%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a solution of 1-(7-bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea (0.125 g, 0.33 mmol) in DMF (5 mL) was added dimethyl-(6-tributylstannanyl-pyridin-2-yl)-amine (0.14 g, 0.33 mmol) under nitrogen atmosphere at room temperature. The reaction mixture was then degassed for half an hour followed by the addition of bis(triphenylphosphine)palladium(II) dichloride (0.023 g, 0.033 mmol). The reaction mixture was then again degassed for half an hour and heated at 100° C. for 15 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), DMF was distilled off; water was added to the reaction mixture and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The crude residue was purified by prep HPLC to get the title compound (0.006 g, 5.0%) as off-white solid.

후처리

  1. customThe reaction mixture was then degassed for half an hour
  2. customThe reaction mixture was then again degassed for half an hour
  3. customAfter the completion of the reaction (TLC monitoring), DMF
  4. distillationwas distilled off
  5. additionwater was added to the reaction mixture
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  8. customevaporated to dryness under reduced pressure
  9. customThe crude residue was purified by prep HPLC

출처 및 근거

ORD 기록
ord-0d3b0de339964f7697c377db49f37a6c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481544B2

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