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

HRID 1173997
Notes
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Reaction equation

HRID 1173997 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.[CH3:26][N:27]1[CH:31]=[CH:30][N:29]=[C:28]1[CH:32]=O.C(OC)(OC)OC.[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][CH2:32][C:28]3[N:27]([CH3:26])[CH:31]=[CH:30][N:29]=3)=[CH:25][CH:24]=2)=[CH:11][CH:12]=1)[CH2:21][CH2:22][CH3:23])[CH2:19][CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 4311764Sodium borohydrideHCID 230791854-aminomethyl-N-(4-dipropylaminomethylphenyl)benzamide

Product 1

HCID 66941901N-(4-dipropylaminomethyl-phenyl)-4-{[(1-methylimidazol-2-ylmethyl)-amino]methyl}benzamideYield 69.3%

Reagents, catalysts & solvents

1
HCID 887MethanolSolvent

Procedure

The compound (290.2 mg) obtained in Example 122-3 was dissolved in methanol (8.71 ml) and added with 1-methyl-2-imidazole carboxaldehyde (141.2 mg) and trimethyl orthoformate (272.2 mg), followed by stirring for 22 hours. The reaction solution was cooled with ice and then added with sodium borohydride (97.0 mg), followed by stirring at room temperature for 0.5 hour. The reaction solution was concentrated under reduced pressure and the residue was then added with water, followed by separation/extraction with chloroform. The organic layer was washed with saturate 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 (256.8 mg) as a yellow oily substance.

Workup

  1. temperatureThe reaction solution was cooled with ice
  2. stirringby stirring at room temperature for 0.5 hour
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionthe residue was then added with water
  5. extractionfollowed by separation/extraction with chloroform
  6. washThe organic layer was washed
  7. concentrationwith saturate saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationfollowed by concentration under reduced pressure
  10. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-e8e70cf328c7409c928d41afb4ee9411
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07833991B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes