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

HRID 1173853Notes

Reaction equation

HRID 1173853 reaction equation
[C:1]([N:8]([CH2:15][C:16]1[CH:35]=[CH:34][C:19]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])=[O:21])=[CH:18][CH:17]=1)[CH2:9][C:10]1[NH:11][CH:12]=[CH:13][N:14]=1)(OC(C)(C)C)=O.[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1C=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:28]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:26][CH2:25][CH2:24][CH2:23][NH:22][C:20](=[O:21])[C:19]1[CH:34]=[CH:35][C:16]([CH2:15][N:8]([CH2:9][C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[CH2:1][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][N:36]=2)=[CH:17][CH:18]=1)[CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 142732-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 210844754-{[N-Boc-N-(1H-imidazol-2-ylmethyl)amino]methyl}-N-(4-dipropylaminobutyl)benzamide

Product 1

HCID 10457708N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-pyridin-2-ylmethylamino]-methyl}-benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (39.8 mg) obtained in Example 1-3 and pyridine-2-aldehyde (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (16.1 mg) were dissolved in anhydrous methanol (2.0 ml). The solution was added with sodium cyanoborohydride (18.9 mg) and then adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 39.5 hours. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and then washed with a 1 mol/l sodium hydroxide and saturated saline solution, followed by drying with anhydrous magnesium sulfate. Subsequently, the residue was distilled off and the residue was then treated with hydrochloric acid. The residue was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (7.00 mg) of the subject compound as a yellow solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with a 1 mol/l sodium hydroxide and saturated saline solution
  5. dry with materialby drying with anhydrous magnesium sulfate
  6. distillationSubsequently, the residue was distilled off
  7. additionthe residue was then treated with hydrochloric acid
  8. customThe residue was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-956b20558de1462dadf550ddc6b1cd90
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

Loading…