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Diisopropylethylamine → 6-((1-(3-Fluoro-5-(trifluoromethyl)benzyl)piperidin-4-yl)amino)pyridazine-3-carbonitrile

HRID 1258157
ノート
印刷プレビュー

反応式

HRID 1258157 の反応式
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C>C(#N)C.ClCCl>[F:10][C:11]1[CH:12]=[C:13]([CH:22]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:24]=1)[CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:2]2[N:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=2)[CH2:17][CH2:16]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

6

反応物 3

HCID 81531DiisopropylethylamineHCID 133828716-Chloropyridazine-3-carbonitrileHCID 532561571-(3-Fluoro-5-trifluoromethyl-benzyl)-piperidin-4-ylamine

生成物 1

HCID 249891986-((1-(3-Fluoro-5-(trifluoromethyl)benzyl)piperidin-4-yl)amino)pyridazine-3-carbonitrile収率 80.5%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒
HCID 6344
Dichloromethane
溶媒

反応条件

温度
120 °C

実験手順

A mixture of 6-chloro-pyridazine-3-carbonitrile (D4) (1.39 g, 9.95 mmol), 1-(3-fluoro-5-trifluoromethyl-benzyl)-piperidin-4-ylamine (D7) (2.5 g, 9.04 mmol) and diisopropylethylamine (2.63 ml, 14.92 mmol) in acetonitrile (2 ml) was stirred at 120° C. for 30 min, under microwave irradiation ((Biotage MW-oven). The mixture was then diluted with dichloromethane (50 ml) and extracted with a saturated solution of sodium carbonate. The organic layer was separated, dried (Na2SO4), filtered, evaporated in vacuo and the residue purified by column chromatography (silica gel; 0-2.5% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. The residue precipitated from diisopropylether to yield E17 (2.76 g, 73%) as a solid. C18H17F4N5 requires 379. Found 380 (MH+); mp: 151.4° C.

後処理

  1. extractionextracted with a saturated solution of sodium carbonate
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customthe residue purified by column chromatography (silica gel; 0-2.5% ammonia in methanol (7M)/dichloromethane)
  7. customThe desired fractions were collected
  8. customevaporated in vacuo
  9. customThe residue precipitated from diisopropylether

出典と根拠

ORDレコード
ord-1ba884f371b745969ada46dcb27749b5
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08466153B2

反応ノート

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