Trimethyl orthoformate → [4-(6-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-1H-inden-2-yl)-butyl]-dipropyl-amine

HRID 2080741Notes

Reaction equation

HRID 2080741 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH2:9]2)=[CH:5][CH:4]=1.[NH:23]1[CH:27]=[CH:26][N:25]=[C:24]1[CH:28]=O.C(OC)(OC)OC.[BH4-].[Na+]>CO>[NH:23]1[CH:27]=[CH:26][N:25]=[C:24]1[CH2:28][NH:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH2:9]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 23155401[4-(6-aminomethyl-1H-inden-2-yl)-butyl]-dipropyl-amine

Product 1

HCID 23155525[4-(6-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-1H-inden-2-yl)-butyl]-dipropyl-amineYield 53.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (40.1 mg) obtained in Example 11-13 was dissolved in methanol (2.0 ml) and added with 2-imidazole carboxaldehyde (19.2 mg) and trimethyl orthoformate (42.5 mg) and the whole was stirred at room temperature for 30 minutes. Subsequently, the solution was added with sodium borohydride (15.1 mg) under ice-cooling, followed by stirring at room temperature for additional 30 minutes. The reaction solution was concentrated under reduced pressure. The residue was added with water, and extracted with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (27.3 mg) as a yellow oily substance.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for additional 30 minutes
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionThe residue was added with water
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationfollowed by concentration under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-2ab924331b2443efbc096bd2385dff56
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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