Acetic Acid → HCID 11950444, compound

HRID 1173967Notes

Reaction equation

HRID 1173967 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-536e449ca8534e8cb68768c7ffb11b84
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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