Triethylamine → [4-(6-Pyridin-2-ylpyridazin-3-YL)piperazin-1-YL]-(2-trifluoromethylphenyl)methanone

HRID 499170ノート

反応式

HRID 499170 の反応式
[N:1]1([C:7]2[N:8]=[N:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:11][CH:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31]>ClCCl>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[N:9]=[N:8][C:7]([N:1]2[CH2:2][CH2:3][N:4]([C:30]([C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[C:27]([F:26])([F:37])[F:38])=[O:31])[CH2:5][CH2:6]2)=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 336763413-Piperazin-1-yl-6-pyridin-2-ylpyridazine

生成物 1

HCID 11596773[4-(6-Pyridin-2-ylpyridazin-3-YL)piperazin-1-YL]-(2-trifluoromethylphenyl)methanone収率 23%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred mixture of 3-piperazin-1-yl-6-pyridin-2-ylpyridazine (0.240 g, 1.000 mmol) and triethylamine (0.7 mL) in dichloromethane (15 mL) at room temperature was added 2-trifluoromethylbenzoyl chloride (0.210 g, 1.000 mmol). After 15 minutes, the mixture was washed with citric acid and NaHCO3. The organic layer was separated, dried over anhydrous MgSO4 and evaporated to yield solid residue, which was crystallized from ether to afford the title compound as a white solid in 23% yield (0.097 g). 1H NMR (300 MHz, CDCl3) δ 8.6 (d, J=4.4 Hz, 1H), 8.5 (d, J=8.0 Hz, 1H), 8.3 (d, J=9.5 Hz, 1H), 7.8 (m, 1H), 7.7 (d, J=7.7 Hz, 1H), 7.6 (t, J=7.3 Hz, 1H), 7.5 (t, J=7.5 Hz, 1H), 7.35 (d, J=7.3 Hz, 1H), 7.28 (m, 1H), 7.0 (d, J=9.5 Hz, 1H), 4.1-3.6 (m, 6H), 3.35-3.31 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 167.6, 159.3, 153.9, 151.4, 148.9, 137.0, 134.4, 132.3, 127.3, 126.8, 123.6, 120.3, 113.1, 46.5, 44.9, 44.6, 41.3. MS (ES+) m/z 414.1 (M+1).

後処理

  1. washthe mixture was washed with citric acid and NaHCO3
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated
  5. customto yield solid residue, which
  6. customwas crystallized from ether

出典と根拠

ORDレコード
ord-cf577922c79c48ea870666ab2ea28502
出典データセット
uspto-grants-2010_08
特許番号
US07767677B2

反応ノート

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