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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
ノート
印刷プレビュー

反応式

HRID 886313 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-ed22cfdc986940fa8c0b14abb70843ce
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08242104B2

反応ノート

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