Ethylenediamine → 5-(1,3-dioxan-2-yl)-N-(2-methoxyethyl)-N-methyl-1H-indazol-3-amine

HRID 1038401ノート

反応式

HRID 1038401 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12](COCC[Si](C)(C)C)[N:11]=[C:10]2[N:24]([CH2:26][CH2:27][O:28][CH3:29])[CH3:25].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(N)CN>C1COCC1>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[N:24]([CH2:26][CH2:27][O:28][CH3:29])[CH3:25]

参加物

5

反応物 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium Fluoride2 回HCID 584076545-(1,3-Dioxan-2-yl)-N-(2-methoxyethyl)-N-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-3-amine

生成物 1

HCID 584075825-(1,3-dioxan-2-yl)-N-(2-methoxyethyl)-N-methyl-1H-indazol-3-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of 245 mg (0.583 mmol) 5-(1,3-dioxan-2-yl)-N-(2-methoxyethyl)-N-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-3-amine (Example 46A) in anhydrous THF (12 ml) were added 8.5 ml (8.5 mmol) tetrabutylammonium fluoride solution (1 M in THF) and ethane-1,2-diamine (200 μl). The solution was stirred at 50° C. for 3 h. After addition of further 8.5 ml tetrabutylammonium fluoride solution (1 M in THF), stirring at 50° C. was continued for 24 h. After cooling, the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium hydrogencarbonate solution and with water. The organic layer was dried with sodium sulfate, filtered and evaporated to dryness. The remaining solid (200 mg, 87% of th.) was used in the next step without further purification.

後処理

  1. stirringstirring at 50° C.
  2. waitwas continued for 24 h
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with saturated aqueous sodium hydrogencarbonate solution and with water
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe remaining solid (200 mg, 87% of th.) was used in the next step without further purification

出典と根拠

ORDレコード
ord-5aafc6647eaa428f8dd1effd3ea53266
出典データセット
uspto-grants-2013_10
特許番号
US08551989B2

反応ノート

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