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

HRID 348602Notes

Reaction equation

HRID 348602 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.C([C:38]1[S:39][CH:40]=[CH:41][N:42]=1)=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:18]=[CH:17][C:16]([CH2:15][N:8]([CH2:9][C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[CH2:1][C:38]2[S:39][CH:40]=[CH:41][N:42]=2)=[CH:35][CH:34]=1)[CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 27349031,3-Thiazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 210844754-{[N-Boc-N-(1H-imidazol-2-ylmethyl)amino]methyl}-N-(4-dipropylaminobutyl)benzamide

Product 1

HCID 10368004N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-thiazol-2-ylmethylamino]-methyl}-benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (39.8 mg) obtained in Example 1-3 and 2-formylthiazole (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (16.9 mg) were dissolved in anhydrous methanol (2.0 ml) and then added with sodium cyanoborohydride (18.9 mg). The solution was adjusted to pH 5 with acetic acid and then stirred 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 1 mol/l sodium hydroxide and saturated saline solution, followed by drying with anhydrous magnesium sulfate. The solvent 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 (9.20 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with 1 mol/l sodium hydroxide and saturated saline solution
  5. dry with materialby drying with anhydrous magnesium sulfate
  6. distillationThe solvent 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-b4a10ba51a3c43829f4f2bd9e50e0a64
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

Loading…