Acetic Acid → HCID 58345784, compound

HRID 2080745Notes

Reaction equation

HRID 2080745 reaction equation
[CH2:1]([N:4]([CH2:27][CH2:28][CH3:29])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH:20][CH2:21][C:22]2[NH:23][CH:24]=[CH:25][N:26]=2)=[CH:15][CH:14]=1)=[O:11])[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][NH:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][N:20]([CH2:21][C:22]2[NH:26][CH:25]=[CH:24][N:23]=2)[CH2:36][C:32]2[N:31]([CH3:30])[CH:35]=[CH:34][N:33]=2)=[CH:17][CH:18]=1)=[O:11])[CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23155396HCID 23155396, compound

Product 1

HCID 58345784HCID 58345784, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (101 mg) obtained in Example 12-3 was dissolved in anhydrous methanol (4.0 ml) and added with 1-methyl-2-imidazole carboxaldehyde (41.8 mg) and sodium cyanoborohydride (47.1 mg). The solution was adjusted to pH 5 by addition of acetic acid, followed by stirring at room temperature for 20 hours. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution and subjected to extraction with chloroform. The extract was dried with magnesium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (80.3 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionThe resultant was added with a 1 mol/l sodium hydroxide aqueous solution
  4. extractionsubjected to extraction with chloroform
  5. dry with materialThe extract was dried with magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  8. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-c4b58e36493f4f1facbb28dd3442790e
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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