Trimethyl orthoformate → 4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-[4-(4-t-butyl-benzylamino)-butyl]-benzamide

HRID 348590Notes

Reaction equation

HRID 348590 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:28]=[CH:27][C:18]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])=[O:20])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.[C:29]([C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)([CH3:32])([CH3:31])[CH3:30].C(OC)(OC)OC.[BH4-].[Na+]>CO>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:28]=[CH:27][C:18]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:37][C:36]2[CH:39]=[CH:40][C:33]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:34][CH:35]=2)=[O:20])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 703244-tert-ButylbenzaldehydeHCID 4311764Sodium borohydrideHCID 103177174-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-aminobutyl)-benzamide

Product 1

HCID 103921624-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-[4-(4-t-butyl-benzylamino)-butyl]-benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (50.6 mg) obtained in Example 3-2 was dissolved in anhydrous methanol (2.0 ml) and added with 4-t-butyl-benzaldehyde (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (0.0330 ml) and trimethyl orthoformate (0.0430 ml), followed by stirring at room temperature for 30 minutes. Then, the solution was added with sodium borohydride (14.8 mg), followed by stirring at room temperature for 15 minutes. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution 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. Subsequently, the residue was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (42.0 mg) of the subject compound as a white solid.

Workup

  1. stirringby stirring at room temperature for 15 minutes
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with a 1 mol/l sodium hydroxide aqueous solution and saturated saline solution
  6. dry with materialby drying with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. additionthe residue was then treated with hydrochloric acid
  9. customSubsequently, the residue was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-231b7d9a0d134a5fbde16abdeb7b9ce1
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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