ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

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

HRID 1666445
ノート
印刷プレビュー

反応式

HRID 1666445 の反応式
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([CH:19]=[C:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][N:6]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33](=O)[O:34]C2C=CC=CC=2)[CH:27]=1.C(N(CC)CC)C>CS(C)=O.O>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([CH:19]=[C:20]2[CH2:21][CH2:22][N:23]([C:33]([NH:32][C:28]3[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=3)=[O:34])[CH2:24][CH2:25]2)=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][N:6]=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 668754652-(2-Chloro-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine

生成物 1

HCID 668761324-(4-chloro-3-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine 1-carboxamide収率 57.3%

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-(2-chloro-5-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (250 mg, 0.677 mmol) in DMSO (3 mL) was added phenyl pyridin-3-ylcarbamate (137.9 mg, 0.643 mmol) followed by triethylamine (0.24 mL, 1.69 mmol). The resulting mixture was stirred at RT for 12 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (30% acetone-70% hexane) to give the pure title compound (180 mg, 54% yield). 1H NMR (500 MHz, CDCl3): δ 8.51 (s, 1H), 8.41 (s, 1H), 8.27 (s, 1H), 8.08 (d, J=7.5 Hz, 1H), 7.95 (d, J=7 Hz, 1H), 7.33 (s, 1H), 7.18 (d, J=3.5 Hz, 2H), 7.12 (d, J=8 Hz, 1H), 6.72 (s, 1H), 6.37 (s, 1H), 3.64 (m, 2H), 3.56 (m, 2H), 2.62 (m, 2H), 2.49 (m, 2H); 13C NMR (125 MHz, CDCl3): δ164.98, 154.54, 147.45, 145.35, 145.32, 143.84, 141.01, 138.68, 136.94, 136.22, 136.10, 130.79, 128.50, 127.62, 127.07, 126.69, 123.61, 123.45, 122.05, 121.78, 111.19, 45.68, 44.61, 40.91, 35.69, 29.14, 28.47; m/z (489.3, 491.1 M+ H+); HPLC: 96.8%.

後処理

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (30% acetone-70% hexane)

出典と根拠

ORDレコード
ord-650af0dd318d472bb710bfac091d1eeb
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

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート