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Acetic Acid → 8-Bromo-2-(2-isopropyl-5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene

HRID 1629343
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HRID 1629343 반응식
[CH:1]([N:4]([C:11]([C:13]1[N:22]=[C:21]2[N:15]([CH2:16][CH2:17][O:18][C:19]3[CH:26]=[C:25]([Br:27])[CH:24]=[CH:23][C:20]=32)[CH:14]=1)=O)[NH:5][C:6](=O)[CH2:7][O:8][CH3:9])([CH3:3])[CH3:2].C(O)(=O)C.[Cl-].[NH4+:33]>O(Cl)Cl.[P+5]>[Br:27][C:25]1[CH:24]=[CH:23][C:20]2[C:21]3[N:15]([CH2:16][CH2:17][O:18][C:19]=2[CH:26]=1)[CH:14]=[C:13]([C:11]1[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[C:6]([CH2:7][O:8][CH3:9])[N:33]=1)[N:22]=3
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참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 25517Ammonium Chloride2회HCID 582046368-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid N-isopropyl-N'-(2-methoxy-acetyl)-hydrazide

생성물 1

HCID 582043878-Bromo-2-(2-isopropyl-5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene수율 76%

시약·촉매·용매 1

HCID 178479711
HCID 178479711, 화합물
용매

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온도
100 °C

실험 절차

8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid N-isopropyl-N′-(2-methoxy-acetyl)-hydrazide (1.00 g, 2.29 mmol) was suspended in phosphorus (V) oxychloride (23 mL) then stirred at 100° C. for 18 h. The reaction mixture was concentrated in vacuo and the residue then azeotroped with toluene (×3) giving a brown solid. To the brown solid was added acetic acid (23 mL) and ammonium chloride (1.76 g, 22.9 mmol), the resultant mixture was stirred at 125° C. for 2.5 h then further ammonium chloride (0.88 g, 11.4 mmol) added, the reaction was stirred at 125° C. for 1 h, then concentrated in vacuo. The resultant residue was treated with water and extracted with DCM (×3). The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution then followed by brine then dried (Na2SO4) and concentrated in vacuo. The resultant solid was triturated with diethyl ether to give 8-Bromo-2-(2-isopropyl-5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene as a light brown solid (0.73 g, 1.74 mmol, 76%). LCMS RT=4.95 min, [M+H]+=418/420. 1H NMR 400 MHz (DMSO-d6) δ: 8.29 (1 H, d, J=8.65 Hz), 7.93 (1 H, s), 7.31 (1 H, dd, J=8.66, 2.05 Hz), 7.25 (1 H, d, J=2.05 Hz), 5.79-5.78 (1 H, m), 4.49 (4 H, s), 4.33 (2 H, s), 3.27 (3 H, s), 1.43 (6 H, d, J=6.60 Hz)

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue then azeotroped with toluene (×3)
  3. customgiving a brown solid
  4. stirringthe reaction was stirred at 125° C. for 1 h
  5. concentrationconcentrated in vacuo
  6. additionThe resultant residue was treated with water
  7. extractionextracted with DCM (×3)
  8. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution
  9. dry with materialthen dried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customThe resultant solid was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-d7c8e2a784c04be7bd6bf4df10219baf
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785626B2

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