Acetic Acid → [4-(5-{[(Imidazol-2-ylmethyl)-(1-methylimidazol-2-ylmethyl)-amino]-methyl}-1-methoxy-indan-2-yl)-butyl]-dipropylamine

HRID 348769Notes

Reaction equation

HRID 348769 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([O:18][CH3:19])[CH:13]([CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[CH2:12]2.[CH3:31][N:32]1[CH:36]=[CH:35][N:34]=[C:33]1[CH:37]=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([O:18][CH3:19])[CH:13]([CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])[CH2:12]2)[CH2:37][C:33]1[N:32]([CH3:31])[CH:36]=[CH:35][N:34]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21084440[4-(5-{[(Imidazol-2-ylmethyl)-amino]-methyl}-1-methoxyindan-2-yl)-butyl]-dipropylamine

Product 1

HCID 21084439[4-(5-{[(Imidazol-2-ylmethyl)-(1-methylimidazol-2-ylmethyl)-amino]-methyl}-1-methoxy-indan-2-yl)-butyl]-dipropylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (54.8 mg) obtained in Example 127-14 was dissolved in methanol (2.74 ml) and added with 1-methyl-2-imidazole carboxaldehyde (21.9 mg) and sodium cyanoborohydride (16.7 mg). Then, the solution was adjusted to pH 4 with acetic acid and stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure and added with saturated saline solution. The solution was subjected to separation/extraction with chloroform. The extract was dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (35.9 mg) of the subject compound as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionadded with saturated saline solution
  3. extractionThe solution was subjected to separation/extraction with chloroform
  4. dry with materialThe extract was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  7. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-0254bd00aabc4f49bd137d9e72adaf1c
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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