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Acetic Acid → N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(1H-pyrazol-3-ylmethyl)-amino]-methyl}-benzamide

HRID 348613
ノート
印刷プレビュー

反応式

HRID 348613 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:28]=[CH:27][CH:26]=[CH:25][C:10]=1C(NCCCCN(CCC)CCC)=O.C([O:34][CH3:35])(OC)OC.[NH:36]1[CH:40]=[CH:39][C:38]([CH:41]=O)=[N:37]1.[C:43]([BH3-])#[N:44].[Na+].[C:47](O)(=O)[CH3:48]>CO>[CH2:26]([N:44]([CH2:43][CH2:47][CH3:48])[CH2:25][CH2:10][CH2:9][CH2:8][NH:7][C:35](=[O:34])[C:26]1[CH:25]=[CH:10][C:9]([CH2:8][N:7]([CH2:6][C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)[CH2:41][C:38]2[CH:39]=[CH:40][NH:36][N:37]=2)=[CH:28][CH:27]=1)[CH2:27][CH3:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 5003444Sodium cyanoborohydrideHCID 122183831H-pyrazole-3-carbaldehydeHCID 86599830[N-(1H-imidazol-2-ylmethyl)amino]methyl-N-(4-dipropylaminobutyl)benzamide

生成物 1

HCID 178457212
N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(1H-pyrazol-3-ylmethyl)-amino]-methyl}-benzamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The compound (53.8 mg) obtained in Example 1-4 was dissolved in methanol (0.8 ml). Then, the solution was added with trimethyl orthoformate (50 μl), acetic acid (50 μl), and pyrazol-3-carboxaldehyde (manufactured by Merck, Inc.) (24.9 mg) and stirred at room temperature for 10 minutes. Subsequently, sodium cyanoborohydride (24.4 mg) was added, followed by stirring overnight at room temperature. The solvent was distilled off under reduced pressure and then the residue was dissolved in chloroform, followed by washing with 1 mol/l sodium hydroxide and saturated saline solution and drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. Then, the residue was then purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (26.1 mg) of the subject compound as a white solid.

後処理

  1. stirringby stirring overnight at room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washby washing with 1 mol/l sodium hydroxide and saturated saline solution
  5. dry with materialdrying with anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThen, the residue was then purified through silica gel column chromatography (chloroform/methanol)
  9. additiontreated with hydrochloric acid

出典と根拠

ORDレコード
ord-9c433abe159a42ed84ff45174e092028
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07176227B2

反応ノート

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