Methanol → 4-{[(1-methyl-1H-imidazol-2-ylmethyl)-(1-trityl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzaldehyde

HRID 2080886Notes

Reaction equation

HRID 2080886 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1)[CH2:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.C(N(C(C)C)CC)(C)C.[C:33](Cl)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CO>ClCCl>[CH3:14][N:10]1[CH:11]=[CH:12][N:13]=[C:9]1[CH2:8][N:7]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH:20]=[O:21])=[CH:22][CH:23]=1)[CH2:6][C:2]1[N:3]([C:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:4]=[CH:5][N:1]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 866149184-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzaldehyde

Product 1

HCID 866149174-{[(1-methyl-1H-imidazol-2-ylmethyl)-(1-trityl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzaldehydeYield 43.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (281 mg) obtained in Example 84-5 was dissolved in dichloromethane (6.0 ml) and added with diisopropylethylamine (310 μl) at room temperature under a nitrogen atmosphere. The solution was added with tritylchloride (310 mg) under ice-cooling and the whole was stirred at room temperature for 4 hours. After completion of the reaction, methanol was added thereto. The solvent was distilled off under reduced pressure and the residue was diluted with chloroform and added with water. The aqueous layer was subjected to extraction with chloroform. The combined organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solution was concentrated and evaporated to dryness under reduced pressure and the residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (217 mg) as a yellow oily substance.

Workup

  1. temperaturecooling
  2. additionwas added
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionthe residue was diluted with chloroform
  5. additionadded with water
  6. extractionThe aqueous layer was subjected to extraction with chloroform
  7. washThe combined organic layer was washed with a saturated saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. concentrationthe solution was concentrated
  11. customevaporated to dryness under reduced pressure
  12. customthe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-adcb2c7420564eaaa34903850786c38b
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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