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1-benzyl-1H-pyrazol-3-amine → N-(1-Benzyl-1H-pyrazol-3-yl)-3-isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzamide

HRID 883053
ノート
印刷プレビュー

反応式

HRID 883053 の反応式
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][CH2:15][CH2:16][C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)[CH:13]=1)[C:8]([OH:10])=O)([CH3:3])[CH3:2].[CH2:22]([N:29]1[CH:33]=[CH:32][C:31]([NH2:34])=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>S(Cl)(Cl)=O>[CH2:22]([N:29]1[CH:33]=[CH:32][C:31]([NH:34][C:8](=[O:10])[C:7]2[CH:11]=[C:12]([O:14][CH2:15][CH2:16][C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)[CH:13]=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH:6]=2)=[N:30]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
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 15086161-benzyl-1H-pyrazol-3-amineHCID 585289133-Isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzoic acid

生成物 1

HCID 25261820N-(1-Benzyl-1H-pyrazol-3-yl)-3-isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzamide収率 45%

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

反応条件

温度
70 °C

実験手順

3-Isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzoic acid (0.672 mmol) is dissolved in thionylchloride (1.2 ml) and heated to 70° C. for 1 hour. After cooling to room temperature, the solvent is removed in vacuo. The residue is dissolved in dichloromethane (1.2 ml) and ethyldiisopropyl-amine (167 μl) is added and 1-benzyl-1H-pyrazol-3-ylamine (1.2 eq) is added. The solution is stirred 21 hours at room temperature. The reaction solution is extracted with water. The organic layer is washed with brine and dried over MgSO4 and the solvent is removed in vacuo. N-(1-Benzyl-1H-pyrazol-3-yl)-3-isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzamide is isolated after column chromatography (heptan /ethylacetate) as yellow oil in a yield of 45%; HPLC (method B): 3.63 min; LC-MS (method B): 2.74 min, 462.2 (MH+); 1H-NMR (DMSO-d5, 500 MHz): δ [ppm] 10.78 (s, 1), 7.79 (d, 1H, J=2.2 Hz), 7.468 (dd, 1H, J=3 Hz, J=4.9 Hz), 7.359-7.269 (m, 4H), 7.245-7228 (m, 2H), 7.174-7.139 (m, 2H), 7.11 (dd, 1H, J=1.1 Hz, J=4.9 Hz), 6.648 (d, 1H, J=2.2 Hz), 5.256 (s, 2H), 4.678 (sep, 1H, J=6 Hz), 4.223 (t, 2H, J=6.9 Hz), 3.049 (t, 2H, J=6.9 Hz), 1.262 (d, 6H, J=6 Hz).

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe solvent is removed in vacuo
  3. dissolutionThe residue is dissolved in dichloromethane (1.2 ml)
  4. additionethyldiisopropyl-amine (167 μl) is added
  5. extractionThe reaction solution is extracted with water
  6. washThe organic layer is washed with brine
  7. dry with materialdried over MgSO4
  8. customthe solvent is removed in vacuo

出典と根拠

ORDレコード
ord-9da74deedd434072b2758162eaa0882b
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08236824B2

反応ノート

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