Acetic Acid → N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(4-methyl-1H-imidazol-5-ylmethyl)-amino]-methyl}-benzamide

HRID 1173868노트

반응식

HRID 1173868 반응식
[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.[CH3:36][C:37]1[N:38]=[CH:39][NH:40][C:41]=1[CH:42]=O.[C:44]([BH3-])#[N:45].[Na+].[C:48](O)(=O)[CH3:49]>CO>[CH2:26]([N:45]([CH2:44][CH2:48][CH3:49])[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)[CH2:36][C:37]2[NH:38][CH:39]=[N:40][C:41]=2[CH3:42])=[CH:28][CH:27]=1)[CH2:27][CH3:28]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 27958875-Methyl-1H-imidazole-4-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86599830HCID 86599830, 화합물

생성물 1

HCID 178457213N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(4-methyl-1H-imidazol-5-ylmethyl)-amino]-methyl}-benzamide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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 4-methyl-5-imidazole carboxaldehyde (manufactured by Aldrich Corporation) (28.5 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 and the residue was then purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (33.5 mg) of the subject compound as a white solid.

후처리

  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. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)
  9. additiontreated with hydrochloric acid

출처 및 근거

ORD 기록
ord-58d294c23924430d8c6db0f9d3bc5f33
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07833991B2

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