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

Water → 2-(2-(3-Methyl-1,2,4-oxadiazol-5-yl)benzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41555
ノート
印刷プレビュー

反応式

HRID 41555 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[N:11]1[CH2:22][CH2:21][C:14]2([C:19](=[O:20])[NH:18][CH2:17][CH2:16][CH2:15]2)[CH2:13][CH2:12]1.[H-].[Na+].Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[O:37][N:36]=[C:35]([CH3:38])[N:34]=1.O>CCCC[N+](CCCC)(CCCC)CCCC.[I-].C1COCC1.C(OCC)(=O)C>[CH3:38][C:35]1[N:34]=[C:33]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH2:26][N:18]2[CH2:17][CH2:16][CH2:15][C:14]3([CH2:21][CH2:22][N:11]([C:2]4[CH:3]=[N:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)[CH2:12][CH2:13]3)[C:19]2=[O:20])[O:37][N:36]=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

8

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 242295032-(3-Methyl-1,2,4-oxadiazol-5-yl)benzyl bromideHCID 672517459-(Quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

生成物 1

HCID 532594672-(2-(3-Methyl-1,2,4-oxadiazol-5-yl)benzyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one収率 98%

試薬・触媒・溶媒 3

HCID 67553
Tetrabutylammonium Iodide
触媒
HCID 8028Tetrahydrofuran溶媒2 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (41 mg, 0.14 mmol) and TBAI (2.6 mg, 6.9 μmol) in THF (0.6 ml) was added sodium hydride (7.0 mg, 95%, 2.8 mmol) at 0° C. The yellow suspension was stirred for 20 min at 0° C. under argon. A solution of 5-(2-(bromomethyl)phenyl)-3-methyl-1,2,4-oxadiazole in dry THF (0.4 ml) was added and stirring was continued for 2 h at rt. To the reaction mixture was added water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over sodium sulfate, filtered and evaporated to give 64 mg (98%) of a pale brown oil. [1H NMR (600 MHz, DMSO-d6) ♀ ppm 8.84 (s, 1H), 8.05 (d, J=7.9 Hz, 1H), 7.81 (d, J=8.3 Hz, 1H), 7.68 (t, J=7.7 Hz, 1H), 7.55-7.62 (m, 2H), 7.51 (t, J=7.8 Hz, 1H), 7.34-7.41 (m, 1H), 7.27 (d, J=7.7 Hz, 1H), 4.91 (s, 2H), 4.23-4.34 (m, 2H), 3.46 (t, J=11.1 Hz, 2H), 3.26-3.32 (m, 2H), 2.44 (s, 3H), 2.04-2.12 (m, 2H), 1.93-2.01 (m, 2H), 1.83-1.92 (m, 2H), 1.66 (d, J=13.5 Hz, 2H); LCMS RtD=2.63 min, [M+H]+=469.2].

後処理

  1. stirringstirring
  2. waitwas continued for 2 h at rt
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washThe organic phases were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-220d14a8c419453d8a0a81a70f3f09a6
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08530648B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート