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Triethylamine → 4-(3-cyclopropyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide

HRID 1666467
ノート
印刷プレビュー

反応式

HRID 1666467 の反応式
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:18]=[C:19]([CH:21]=[C:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:20]=2)[O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=2)[CH2:3][CH2:2]1.[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35](=[O:43])OC2C=CC=CC=2)C=1.C([N:46](CC)CC)C>CS(C)=O.O>[CH:1]1([C:4]2[CH:20]=[C:19]([CH:18]=[C:6]([O:7][C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][N:9]=3)[CH:5]=2)[CH:21]=[C:22]2[CH2:23][CH2:24][N:25]([C:35]([NH:34][C:30]3[N:46]=[N:28][CH:33]=[CH:32][CH:31]=3)=[O:43])[CH2:26][CH2:27]2)[CH2:2][CH2:3]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 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 668754182-(3-Cyclopropyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

生成物 1

HCID 249679964-(3-cyclopropyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide収率 66%

試薬・触媒・溶媒 2

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒

実験手順

To a solution of 2-(3-cyclopropyl-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (0.15 g, 0.401 mmol) and phenyl pyridin-3-ylcarbamate (85.8 mg, 0.4 mmol) in DMSO (1.5 mL) was added triethylamine (0.55 mL, 4.0 mmol) and the mixture was stirred overnight. The reaction mixture was diluted with water and extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4, and evaporated to dryness. The residue was purified by silica gel column chromatography (38% acetone in hexane) to give the title compound (0.13 g, 66%). 1H NMR (500 MHz, CDCl3): δ 8.77 (s, 1H), 8.45 (s, 1H), 8.41 (s, 1H), 7.89 (d, J=8.5 Hz, 1H), 7.47 (t, J=4.5 Hz, 1H), 6.99 (d, J=8.5 Hz, 1H), 6.81 (s, 1H), 6.77 (s, 1H), 6.70 (s, 1H), 6.38 (s, 1H), 3.70 (m, 2H), 3.60 (m, 2H), 2.60 (m, 2H), 2.47 (d, 2H), 1.87 (m, 1H), 0.98 (d, J=8 Hz, 2H), 0.70 (d, J=4.5 Hz, 2H). 13C NMR (125 MHz, CDCl3): δ 165.83, 156.60, 153.17, 146.31, 145.54, 138.65, 137.71, 136.70, 128.20, 124.83, 123.63, 118.77, 116.75, 111.30, 45.64, 44.62, 35.73, 29.21, 15.44, 9.51; m/z (496.2, M+ H+); HPLC: 98.6%.

後処理

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel column chromatography (38% acetone in hexane)

出典と根拠

ORDレコード
ord-e4b0309b35264d6fb87c826d34d5afa4
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08044052B2

反応ノート

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