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Potassium Carbonate → 6-[4-Methyl-4-(2-trifluoromethylphenoxy)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide

HRID 552167
ノート
印刷プレビュー

反応式

HRID 552167 の反応式
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.[CH3:16][C:17]1([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:20]3[CH2:19][CH2:18][C:17]([CH3:16])([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:31])([F:32])[F:33])[CH2:22][CH2:21]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamideHCID 671715074-Methyl-4-(2-trifluoromethylphenoxy)piperidine

生成物 1

HCID 115396356-[4-Methyl-4-(2-trifluoromethylphenoxy)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide収率 20%

試薬・触媒・溶媒 2

HCID 74236
Tetrabutylammonium Bromide
触媒
HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.020 g, 0.090 mmol) in dioxane (5 mL) was added 4-methyl-4-(2-trifluoromethylphenoxy)piperidine (0.015 g, 0.060 mmol), potassium carbonate (0.033 g, 0.240 mmol) and tetrabutyl ammonium bromide (0.002 g, 0.001 mmol). The resulting mixture was stirred at reflux for 48 hours, filtered and then concentrated in vacuo. The crude product was purified by column chromatography to yield the title compound in 20% yield (0.005 g). 1H NMR (300 MHz, CDCl3) δ 8.02-7.96 (m, 2H), 7.60-7.57 (m, 1H), 7.48-7.40 (m, 1H), 7.14-7.12 (d, J=8.0 Hz, 1H), 7.06-6.99 (m, 2H), 4.25-4.21 (m, 2H), 3.65-3.51 (m, 4H), 2.35-2.31 (m, 2H), 1.85-1.74 (m, 2H), 1.53-1.46 (dd, J=6.6 and 7.0 Hz, 2H), 1.20 (s, 3H), 0.77-0.69 (m, 1H), 0.48-0.42 (m, 2H), 0.11-0.05 (m, 2H). MS (ES+) m/z 449.4 (M+1).

後処理

  1. temperatureat reflux for 48 hours
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-ecdf6e9ce59441179dbb6b993c0550da
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07951805B2

反応ノート

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