Propanal → HCID 10432329, compound

HRID 1173871Notes

Reaction equation

HRID 1173871 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.C([BH3-])#N.[Na+].C(OC)(OC)OC.[CH:40](=O)[CH2:41][CH3:42]>CO>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([N:23]2[CH2:24][CH2:25][N:26]([CH2:40][CH2:41][CH3:42])[CH2:27][CH2:28]2)=[O:22])=[CH:19][CH:20]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 527PropanalHCID 9005Trimethyl orthoformateHCID 5003444Sodium cyanoborohydrideHCID 21084462(4-{[bis-(1H-imidazol-2-ylmethyl)-amino]-methyl}-phenyl)-piperazin-1-yl-methanone

Product 1

HCID 10432329HCID 10432329, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (48.8 mg) obtained in Example 32-2 was dissolved in anhydrous methanol (1.0 ml) and then added with sodium cyanoborohydride (16.2 mg), trimethyl orthoformate (21.1 μl), propionaldehyde (13.9 μl), followed by stirring overnight at room temperature under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform. A saturated aqueous sodium bicarbonate solution was added to the solution, followed by stirring. The resultant solution was subjected to extraction with chloroform and washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution, and then the organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then treated with hydrochloric acid. Subsequently, the treated product was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (33.2 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was then dissolved in chloroform
  4. additionA saturated aqueous sodium bicarbonate solution was added to the solution
  5. stirringby stirring
  6. extractionThe resultant solution was subjected to extraction with chloroform
  7. washwashed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  8. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. additionthe residue was then treated with hydrochloric acid
  11. customSubsequently, the treated product was purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-824ce398f8f546a39bfc06a4c7512942
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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