Trimethyl orthoformate → {3-[6-(4-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-pyridin-2-yl]-propyl}-dipropyl-amine

HRID 2080807Notes

Reaction equation

HRID 2080807 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH2:15][CH2:16][CH2:17][N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O.C(OC)(OC)OC.[BH4-].[Na+]>CO>[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH2:30][NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([CH2:15][CH2:16][CH2:17][N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 23155536{3-[6-(4-Aminomethyl-phenyl)-pyridin-2-yl]-propyl}-dipropyl-amine

Product 1

HCID 23155577{3-[6-(4-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-pyridin-2-yl]-propyl}-dipropyl-amineYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An anhydrous methanol solution (0.50 ml) containing the compound (30.1 mg) obtained in Example 36-5 and 2-imidazole carboxaldehyde (10.1 mg) was added with trimethyl orthoformate (0.029 ml), and the whole was stirred at room temperature for 14 hours. Sodium borohydride (17.0 mg) was added thereto and the whole was stirred for 30 minutes. The solvent was distilled off. The residue was dissolved in chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution, and dried with anhydrous sodium sulfate, and the solvent was distilled off, thereby obtaining the subject compound (30.4 mg).

Workup

  1. stirringthe whole was stirred for 30 minutes
  2. distillationThe solvent was distilled off
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-3a4675ad9bf44f56bbd09db7f87886d4
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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