Nitronium tetrafluoroborate → 1-(7-Hydroxy-6-nitro-2-benzothiazolyl)-3-ethyl-urea

HRID 9118

반응식

HRID 9118 반응식
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[OH:9][C:10]1[C:18]2[S:17][C:16]([NH:19][C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[N:15][C:14]=2[CH:13]=[CH:12][CH:11]=1>C(#N)C.C(OCC)C>[OH:9][C:10]1[C:18]2[S:17][C:16]([NH:19][C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[N:15][C:14]=2[CH:13]=[CH:12][C:11]=1[N+:7]([O-:8])=[O:6]

참가 물질

5

반응물 2

HCID 11073463Nitronium tetrafluoroborateHCID 219855231-(7-Hydroxy-2-benzothiazolyl)-3-ethyl-urea

생성물 1

HCID 219856421-(7-Hydroxy-6-nitro-2-benzothiazolyl)-3-ethyl-urea수율 10.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매2회

반응 조건

온도
20 °C

실험 절차

To a solution of 2-methylpyridone (0.020 mL, 0.20 mmol, 1.2 eq) in anhydrous acetonitrile (0.5 mL), nitronium tetrafluoroborate (0.045 g, 0.32 mmol, 1.9 eq) was added. The suspension was stirred at about 20° C. for about 5 minutes to get an orange solution. The solution was then transferred to a suspension of 1-(7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 8 (0.040 g, 0.17 mmol) in acetonitrile (0.5 mL). The reaction mixture was stirred at about 20° C. for about 15 minutes, then taken up in diethyl ether (8 mL), and neutralized by washing with saturated sodium bicarbonate solution (1.5 mL). The organic extract was concentrated and dissolved in methanol (2 mL). LC/MS purification was followed by flash chromatography purification on silica (methylene chloride/methanol=40/1) to afford 0.005 g (10%) of the desired compound 17. 1H NMR (DMSO) δ 11.20 (br s, 1H, NH), 8.02 (d, 1H, J=9.0 Hz, ArH), 7.23 (d, 1H, J=7.5 Hz, ArH), 6.78 (br s, 1H, NH), 3.20 (m, 2H, CH2), 1.10 (t, 3H, J=7.2 Hz, CH3). LC/MS 283 (MH+); RP-HPLC RT 2.74 minutes.

후처리

  1. customto get an orange solution
  2. stirringThe reaction mixture was stirred at about 20° C. for about 15 minutes
  3. washby washing with saturated sodium bicarbonate solution (1.5 mL)
  4. extractionThe organic extract
  5. concentrationwas concentrated
  6. dissolutiondissolved in methanol (2 mL)
  7. customLC/MS purification
  8. customwas followed by flash chromatography purification on silica (methylene chloride/methanol=40/1)

출처 및 근거

ORD 기록
ord-c336b764197e420a978d946859501796
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

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