N-methyl-2-pyrrolidone → (S)-10-{3-[2-(4-Methoxy-phenyl)-ethyl]-piperazin-1-yl}-2-methyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

HRID 1350455ノート

反応式

HRID 1350455 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C@H:11]2[CH2:16][NH:15][CH2:14][CH2:13][NH:12]2)=[CH:5][CH:4]=1.[CH3:17][C:18]1[S:27][C:26]2[NH:25][C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[N:22]=[C:21](N)[C:20]=2[N:19]=1.CN1CCCC1=O>C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C@@H:11]2[NH:12][CH2:13][CH2:14][N:15]([C:21]3[C:20]4[N:19]=[C:18]([CH3:17])[S:27][C:26]=4[NH:25][C:24]4[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=4[N:22]=3)[CH2:16]2)=[CH:7][CH:8]=1

参加物

6

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 21093530HCID 21093530、化合物HCID 1357977442-methyl-4H-3-thia-1,4,9-triazabenzo[f]azulene-10-ylamine

生成物 1

HCID 136005561(S)-10-{3-[2-(4-Methoxy-phenyl)-ethyl]-piperazin-1-yl}-2-methyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene収率 109.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
195 °C

実験手順

Combine (S)-2-[2-(4-methoxy-phenyl)-ethyl]-piperazine (180 mg, 0.82 mmol), 2-methyl-4H-3-thia-1,4,9-triaza-benzo[f]azulen-10-ylamine (188 mg, 0.82 mmol), 1-methyl-2-pyrrolidinone (5 mL). Heat at 195° C. After 3.75 h, cool to ambient temperature and stir 18 h. Combine with another 2.30 mmol reaction executed under same conditions. Dilute with ethyl acetate and water. Extract with ethyl acetate. Wash the extracts with water and brine, dry over sodium sulfate, filter and concentrate the filtrate. Purify by silica gel chromatography using 2N ammonia in methanol-methylene chloride (2.5%–4%) as the eluent to give 388 mg (29%) of the title compound: mass spectrum (ion spray): m/z=434 (M+1), 432 (M−1). HR-MS calculated for C24H28N5OS: 434.2015. Found 434.201 HPLC: Symmetry C18 column (3.5 μm, 4.6×50 mm). Gradient 5% to 90% solvent B in 7 min. Solvent A was 0.1% (v/v) TFA in water and solvent B was acetonitrile. Retention time 5.4 min; 100% pure.

後処理

  1. temperaturecool to ambient temperature
  2. customCombine with another 2.30 mmol reaction
  3. extractionExtract with ethyl acetate
  4. washWash the extracts with water and brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate the filtrate
  8. customPurify by silica gel chromatography

出典と根拠

ORDレコード
ord-0f31fc04ad8b46888d540b59683f06f7
出典データセット
uspto-grants-2007_05
特許番号
US07214673B2

反応ノート

読み込み中…