Water → HCID 178458210、化合物

HRID 2110027ノート

反応式

HRID 2110027 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]([CH:37]([OH: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.O>CN(C)C=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[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]([CH:37]([OH: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 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 69070100HCID 69070100、化合物

生成物 1

HCID 178458210HCID 178458210、化合物

試薬・触媒・溶媒 2

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-ol (50 mg, 0.073 mmol) in anhydrous dimethylformamide (2 ml), tetrabutylammonium fluoride (0.5 ml, 1.0 M tetrahydrofuran solution) was added and the mixture was stirred at 100° C. for 13 hours. Ethyl acetate and water were added, after which the aqueous layer was adjusted to pH 11 and extracted 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 (ethyl acetate/methanol=4/1). The purified product was further purified by preparative HPLC to obtain 1-{2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-amino]-1H-benzimidazol-5-yl}-propan-1-ol.

後処理

  1. additionwas added
  2. extractionextracted with ethyl acetate
  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 (ethyl acetate/methanol=4/1)
  7. customThe purified product was further purified by preparative HPLC

出典と根拠

ORDレコード
ord-063f6a2f022c49d48c4897d370cbc7a5
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…