Acetic Acid → HCID 11950444, compound

HRID 348714Notes

Reaction equation

HRID 348714 reaction equation
[CH2:1]([N:4]([CH2:27][CH2:28][CH3:29])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:26])[C:10](=[O:25])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][CH2:19][C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)=[CH:13][CH:12]=1)[CH2:2][CH3:3].[CH3:30][N:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:27]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:26])[C:10](=[O:25])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:19][C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)[CH2:36][C:32]2[N:31]([CH3:30])[CH:35]=[CH:34][N:33]=2)=[CH:13][CH:12]=1)[CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21084502HCID 21084502, compound

Product 1

HCID 11950444HCID 11950444, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (266.9 mg) obtained in Example 111-1 was dissolved in anhydrous methanol (11 ml) and then added with 1-methyl-2-imidazole carboxaldehyde (110.1 mg) and sodium cyanoborohydride (84.2 mg). Then, the solution was adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 3 days. After the reaction, the solvent was distilled off. The residue was added with a 1 mol/l sodium hydroxide aqueous solution (1.0 ml) and extracted with chloroform. The extract was dried with magnesium sulfate. The solvent was distilled off. Then, the residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (234.9 mg) of the subject compound as a white solid.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionThe residue was added with a 1 mol/l sodium hydroxide aqueous solution (1.0 ml)
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried with magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customThen, the residue was purified through silica gel column chromatography (chloroform/methanol)
  8. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-01703afcc9984aefb694a4af2a00a8ed
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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