Triethylamine → 2-(Naphthalen-1-ylmethyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41542

反応式

HRID 41542 の反応式
Cl.[C:2]1([N:12]2[CH:17](C)[CH2:16][CH2:15][C:14]3([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:13]2=[O:24])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.Cl[C:26]1[CH:35]=[N:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1.[CH2:36](N(CC)CC)C>CCO>[C:11]1([CH2:2][N:12]2[CH2:17][CH2:16][CH2:15][C:14]3([CH2:19][CH2:20][N:21]([C:26]4[CH:35]=[N:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[CH2:22][CH2:23]3)[C:13]2=[O:24])[C:6]2[C:7](=[CH:8][CH:3]=[CH:4][CH:5]=2)[CH:36]=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2389382-ChloroquinoxalineHCID 672523132-Naphthalen-1-yl-methyl-2,9-diaza-spiro[5.5]undecan-1-one hydrochloride

生成物 1

HCID 532591112-(Naphthalen-1-ylmethyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one収率 68.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
160 °C

実験手順

Crude 2-naphthalen-1-yl-methyl-2,9-diaza-spiro[5.5]undecan-1-one hydrochloride (100 mg, 0.29 mmol), 2-chloro-quinoxaline (81 mg, 0.49 mmol) and triethylamine (0.12 ml, 0.87 mmol) were dissolved in EtOH (1 ml) in a microwave tube. The tube was sealed and the suspension was heated at 160° C. over 20 min under microwave conditions. The solvent was removed under reduced pressure and the resulting crude product was purified by preparative reverse phase chromatography (Sun Fire C18 column, 16 min linear gradient: elution 20-60% (CH3CN in H2O (0.1% TFA)); flow rate 50 ml/min) to yield 87 mg (53%) of the title compound. [1H NMR (DMSO, 600 MHz) δ 8.86 (s, 1H), 8.07-8.00 (m, 1H), 7.98-7.91 (m, 1H), 7.86 (d, 1H, J=8.28 Hz), 7.82 (d, 1H, J=8.02 Hz), 7.64-7.56 (m, 2H), 7.56-7.50 (m, 2H), 7.48 (t, 1H), 7.38 (t, 1H), 7.34 (d, 1H, J=7.06 Hz), 4.98 (s, 2H), 4.37-4.26 (m, 2H), 3.46 (t, 2H), 3.23-3.10 (m, 2H), 2.20-2.08 (m, 2H), 1.93-1.82 (m, 2H), 1.80-1.70 (m, 2H), 1.67-1.53 (m, 2H), LCMS RtD=3.10 min, [M+H]+=437.2].

後処理

  1. customThe tube was sealed
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting crude product was purified by preparative reverse phase chromatography (Sun Fire C18 column, 16 min linear gradient: elution 20-60% (CH3CN in H2O (0.1% TFA)); flow rate 50 ml/min)

出典と根拠

ORDレコード
ord-4ae20f03f4a34420a6c9c32528453826
出典データセット
uspto-grants-2013_09
特許番号
US08530648B2

関連ノート

読み込み中…