Ethyl Acetate → HCID 178458209、化合物

HRID 2110029ノート

反応式

HRID 2110029 の反応式
[C:1]1([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][N:19](COCC[Si](C)(C)C)[C:20]3[N:24](COCC[Si](C)(C)C)[C:23]4[CH:33]=[CH:34][C:35]([C:37](=[O:40])[CH2:38][CH3:39])=[CH:36][C:22]=4[N:21]=3)[CH2:14][CH2:13]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(OCC)(=O)C>CN(C)C=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]1([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][NH:19][C:20]3[NH:24][C:23]4[CH:33]=[CH:34][C:35]([C:37](=[O:40])[CH2:38][CH3:39])=[CH:36][C:22]=4[N:21]=3)[CH2:14][CH2:13]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 2

HCID 8857Ethyl AcetateHCID 69067810HCID 69067810、化合物

生成物 1

HCID 178458209HCID 178458209、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 2724141Tetrabutylammonium Fluoride溶媒

反応条件

温度
100 °C

実験手順

After dissolving 1-[2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-5-yl]-propan-1-one (32 mg, 0.047 mmol) in anhydrous dimethylformamide (1 ml), tetrabutylammonium fluoride (0.8 ml, 1.0 M tetrahydrofuran solution) and water (5 μl) were added, and the mixture was stirred at 100° C. for 2 hours and 30 minutes. Water and ethyl acetate were added, and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by thin-layer silica gel chromatography (dichloromethane/methanol/TEA=85/10/1). The purified product was further purified by preparative HPLC and thin-layer silica gel chromatography (dichloromethane/methanol=8/2) to obtain 1-{2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-amino]-1H-benzimidazol-5-yl}-propan-1-one.

後処理

  1. additionwere added
  2. extractionextraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by thin-layer silica gel chromatography (dichloromethane/methanol/TEA=85/10/1)
  7. customThe purified product was further purified by preparative HPLC and thin-layer silica gel chromatography (dichloromethane/methanol=8/2)

出典と根拠

ORDレコード
ord-77c4cb1daf944e08b63e9e372fc7ec3c
出典データセット
uspto-grants-2009_04
特許番号
US07517875B2

反応ノート

読み込み中…