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Methoxyacetyl chloride → 8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid N-isopropyl-N'-(2-methoxy-acetyl)-hydrazide

HRID 886313
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 886313
Cl.Cl.[CH:3]([N:6]([C:8]([C:10]1[N:19]=[C:18]2[N:12]([CH2:13][CH2:14][O:15][C:16]3[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:17]=32)[CH:11]=1)=[O:9])[NH2:7])([CH3:5])[CH3:4].[CH3:25][O:26][CH2:27][C:28](Cl)=[O:29]>C(Cl)Cl>[CH:3]([N:6]([C:8]([C:10]1[N:19]=[C:18]2[N:12]([CH2:13][CH2:14][O:15][C:16]3[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:17]=32)[CH:11]=1)=[O:9])[NH:7][C:28](=[O:29])[CH2:27][O:26][CH3:25])([CH3:5])[CH3:4]
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Komponenten

4

Edukt 2

HCID 96623Methoxyacetyl chlorideHCID 670507018-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid N-isopropyl-hydrazide dihydrochloride

Produkt 1

HCID 582046368-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid N-isopropyl-N'-(2-methoxy-acetyl)-hydrazideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of 8-bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid N-isopropyl-hydrazide dihydrochloride (2.69 g, 6.1 mmol) in DCM (61 mL) was treated with TEA (3.84 mL, 27.6 mmol). The resultant solution was cooled to 0° C. before methoxyacetyl chloride (1.12 mL, 12.3 mmol) was added dropwise and the reaction stirred at 0° C. for 1.75 h. The reaction was quenched with saturated sodium bicarbonate solution and the phases separated. The aqueous phase was extracted with DCM (×2) before the combined organic phases were washed sequentially with 10% citric acid solution, saturated sodium bicarbonate solution and brine. The organic solution was dried (Na2SO4), concentrated in vacuo and the resultant solid was triturated with diethyl ether to give 8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid N-isopropyl-N′-(2-methoxy-acetyl)-hydrazide as an off-white solid (2.29 g, 5.24 mmol, 86%). LCMS RT=4.29 min, [M+H]+=437/439. 1H NMR 400 MHz (DMSO-d) δ: 9.61 (1H, s), 8.29 (1H, d, J=8.63 Hz), 7.71 (1H, s), 7.27 (1H, dd, J=8.64, 2.06 Hz), 7.21 (1H, d, J=2.06 Hz), 4.84 (1H, t, J=6.91 Hz), 4.45 (4H, s), 3.92 (2H, s), 3.33 (3H, s), 1.15 (6H, d, J=6.66 Hz)

Aufarbeitung

  1. additionwas added dropwise
  2. customThe reaction was quenched with saturated sodium bicarbonate solution
  3. customthe phases separated
  4. extractionThe aqueous phase was extracted with DCM (×2) before the combined organic phases
  5. washwere washed sequentially with 10% citric acid solution, saturated sodium bicarbonate solution and brine
  6. dry with materialThe organic solution was dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customthe resultant solid was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ed22cfdc986940fa8c0b14abb70843ce
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08242104B2

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