Acetic Acid → HCID 10028389, compound

HRID 348627Notes

Reaction equation

HRID 348627 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]([CH2:19][N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.C([BH3-])#N.[Na+].C(O)(=O)C.[NH:39]1[CH:43]=[CH:42][N:41]=[C:40]1[CH:44]=O>CO>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:19][N:20]([CH2:21][CH2:22][CH3:23])[CH2:24][CH2:25][CH3:26])=[CH:27][CH:28]=2)=[CH:11][CH:10]=1)[CH2:44][C:40]1[NH:39][CH:43]=[CH:42][N:41]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21084427HCID 21084427, compound

Product 1

HCID 10028389HCID 10028389, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (20.4 mg) obtained in Example 35-5 was dissolved in anhydrous methanol (2.0 ml) and added with sodium cyanoborohydride (9.50 mg), acetic acid (2.0 ml), and 2-imidazole carboxaldehyde (9.60 mg), followed by stirring at room temperature under a nitrogen atmosphere for 6.5 hours and a half. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and added with a saturated aqueous sodium bicarbonate solution, followed by stirring. The solution was subjected to extraction with chloroform and the extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution. Subsequently, the organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, and the residue was treated with hydrochloric acid and then purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (4.50 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 dissolved in chloroform
  4. additionadded with a saturated aqueous sodium bicarbonate solution
  5. stirringby stirring
  6. extractionThe solution was subjected to extraction with chloroform
  7. washthe extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  8. dry with materialSubsequently, the organic layer was dried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. additionthe residue was treated with hydrochloric acid
  11. custompurified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-e4aad25b0190429f9950611380cee043
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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