Trimethyl orthoformate → N-(4-dipropylaminomethyl-phenyl)-4-{[(1-methylimidazol-2-ylmethyl)-amino]methyl}benzamide

HRID 2080758Notes

Reaction equation

HRID 2080758 reaction equation
[NH2:1][CH2:2][C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1.[CH:26](OC)(OC)OC.[NH:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH:38]=O.[BH4-].[Na+]>CO>[CH2:18]([N:17]([CH2:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([CH2:2][NH:1][CH2:38][C:34]3[N:35]([CH3:26])[CH:36]=[CH:37][N:33]=3)=[CH:25][CH:24]=2)=[CH:11][CH:12]=1)[CH2:21][CH2:22][CH3:23])[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 230791854-aminomethyl-N-(4-dipropylaminomethylphenyl)benzamide

Product 1

HCID 66941901N-(4-dipropylaminomethyl-phenyl)-4-{[(1-methylimidazol-2-ylmethyl)-amino]methyl}benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (389 mg) obtained in Example 15-4 was dissolved in anhydrous methanol (10 ml) and then added with trimethyl orthoformate (188 μl) and 2-imidazole carboxaldehyde (139 mg). The whole was stirred overnight at room temperature under a nitrogen atmosphere. Then, sodium borohydride (43.4 mg) was added thereto in an ice bath and the whole was stirred at room temperature for 2.5 hours. After completion of the reaction, distilled water was added thereto and the whole was stirred for a while. The solution was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (346 mg) as a yellow solid.

Workup

  1. stirringin an ice bath and the whole was stirred at room temperature for 2.5 hours
  2. customAfter completion of the reaction
  3. distillationdistilled water
  4. additionwas added
  5. stirringthe whole was stirred for a while
  6. extractionThe solution was subjected to extraction with chloroform
  7. washwashed with a saturated saline solution
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. distillationthe solvent was then distilled off
  10. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-f54e52b52b594fdc881415d78947e256
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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