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1-Isopropylhydrazine hydrochloride → 9-Bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene

HRID 886075
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인쇄 미리보기

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HRID 886075 반응식
C[N:2](C)[CH:3]=[N:4][C:5]([C:7]1[CH:8]=[C:9]2[N:15]([N:16]=1)[C:14]1[CH:17]=[C:18]([Br:21])[CH:19]=[CH:20][C:13]=1[O:12][CH2:11][CH2:10]2)=O.Cl.[CH:24]([NH:27]N)([CH3:26])[CH3:25]>C(O)(=O)C>[Br:21][C:18]1[CH:19]=[CH:20][C:13]2[O:12][CH2:11][CH2:10][C:9]3[N:15]([N:16]=[C:7]([C:5]4[N:27]([CH:24]([CH3:26])[CH3:25])[N:2]=[CH:3][N:4]=4)[CH:8]=3)[C:14]=2[CH:17]=1
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참가 물질

4

반응물 2

HCID 855731-Isopropylhydrazine hydrochlorideHCID 582044179-Bromo-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-2-carboxylic acid 1-dimethylaminomethylideneamide

생성물 1

HCID 582047309-Bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene수율 76%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
110 °C

실험 절차

A mixture of 9-bromo-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene-2-carboxylic acid 1-dimethylaminomethylideneamide (1.27 g, 3.5 mmol), isopropylhydrazine hydrochloride (0.48 g, 4.37 mmol) and glacial acetic acid (6 mL) was heated at 110° C. for 6.5 h, then cooled and concentrated in vacuo. The resultant residue was dissolved in aqueous sodium bicarbonate and DCM and the phases were separated. The aqueous phase was extracted several times with DCM, the combined organic extracts dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 30 to 70% ethyl acetate in cyclohexane) to give 9-Bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene (0.99 g, 76%). LCMS: RT=5.07 min, M+H+=374/376. 1H NMR δ (ppm) (CDCl3): 8.07 (1H, d, J=2.41 Hz), 7.96 (1H, s), 7.39 (1H, dd, J=8.63, 2.43 Hz), 7.08 (1H, d, J=8.63 Hz), 6.91 (1H, s), 5.73-5.65 (1H, m), 4.53 (2H, t, J=5.91 Hz), 3.18 (2H, t, J=5.91 Hz), 1.60 (6H, d, J=6.62 Hz)

후처리

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resultant residue was dissolved in aqueous sodium bicarbonate
  4. customDCM and the phases were separated
  5. extractionThe aqueous phase was extracted several times with DCM
  6. dry with materialthe combined organic extracts dried (MgSO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-462235b466be46f29fbd24ca61b6f7e7
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08242104B2

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