Morpholine → 8-Chloro-4-(3-{[3-(morpholin-4-ylcarbonyl)benzyl]oxy}phenyl)-3-phenylcinnoline

HRID 643329ノート

反応式

HRID 643329 の反応式
C[Al](C)C.[NH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C[O:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[C:37]4[C:32](=[C:33]([Cl:38])[CH:34]=[CH:35][CH:36]=4)[N:31]=[N:30][C:29]=3[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:23]=2)[CH:15]=1>C1(C)C=CC=CC=1>[Cl:38][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:32]=1[N:31]=[N:30][C:29]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[C:28]2[C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH2:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([N:5]3[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)=[O:12])[CH:15]=2)[CH:23]=1

参加物

5

反応物 3

HCID 8083MorpholineHCID 16682925TrimethylaluminumHCID 685788903-[3-(8-Chloro-3-phenyl-cinnolin-4-yl)-phenoxymethyl]-benzoic acid methyl ester

生成物 1

HCID 118548288-Chloro-4-(3-{[3-(morpholin-4-ylcarbonyl)benzyl]oxy}phenyl)-3-phenylcinnoline

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
60 °C

実験手順

A solution of trimethylaluminum (2 M solution in dichloromethane, 0.5 M) was added to a solution of morpholine (0.1 g) in 5 mL of toluene at room temperature. After 30 minutes 3-[3-(8-chloro-3-phenyl-cinnolin-4-yl)-phenoxymethyl]-benzoic acid methyl ester (50 mg) in 2 mL of toluene was added and the solution was heated to 60° C. for 15 hours. The reaction mixture was cooled to room temperature, quenched with diluted HCl and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by semi-preparative HPLC. MS (ES) m/z 536.2.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with diluted HCl
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by semi-preparative HPLC

出典と根拠

ORDレコード
ord-66ef48f8ae354f8c96e89b6d5357e27e
出典データセット
uspto-grants-2010_04
特許番号
US07700595B2

反応ノート

読み込み中…