Acetic Acid → HCID 21084423, compound

HRID 348658Notes

Reaction equation

HRID 348658 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=1.C([BH3-])#N.[Na+].C(O)(=O)C.[NH:36]1[CH:40]=[CH:39][N:38]=[C:37]1[CH:41]=O>CO>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH3:25])=[CH:11][CH:10]=1)[CH2:41][C:37]1[NH:36][CH:40]=[CH:39][N:38]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21084428HCID 21084428, compound

Product 1

HCID 21084423HCID 21084423, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The compound (81.2 mg) obtained in Example 60-4 was dissolved in anhydrous methanol (2.0 ml) and then added with sodium cyanoborohydride (27.4 mg), acetic acid (3.00 ml), and 2-imidazole carboxaldehyde (31.4 mg), followed by stirring under a nitrogen atmosphere at 60° C. for 4 days. After completion of the reaction, the solvent was distilled off. Then, the residue was dissolved in chloroform and added with a saturated aqueous sodium bicarbonate solution, followed by stirring. The aqueous layer was washed with chloroform and then evaporated to dryness. The residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (63.0 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThen, the residue was dissolved in chloroform
  4. additionadded with a saturated aqueous sodium bicarbonate solution
  5. stirringby stirring
  6. washThe aqueous layer was washed with chloroform
  7. customevaporated to dryness
  8. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  9. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-d4bc88f1295a46a6bd7194885fa26021
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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