Acetic Acid → HCID 66941754, compound

HRID 348685Notes

Reaction equation

HRID 348685 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[N:10]([CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=O)[C:20]2[CH:25]=[CH:24][C:23]([CH2:26][NH:27][CH2:28][C:29]3[NH:30][CH:31]=[CH:32][N:33]=3)=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:42][N:43]1[CH:47]=[CH:46][N:45]=[C:44]1[CH:48]=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:1]([O:8][C:9](=[O:41])[N:10]([CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1)[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]([CH2:28][C:29]3[NH:33][CH:32]=[CH:31][N:30]=3)[CH2:48][C:44]3[N:43]([CH3:42])[CH:47]=[CH:46][N:45]=3)=[CH:22][CH:21]=2)=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66941300HCID 66941300, compound

Product 1

HCID 66941754HCID 66941754, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (236 mg) obtained in Example 87-4 and 1-methyl-2-imidazole carboxaldehyde (46.5 mg) were dissolved in anhydrous methanol (7.1 ml). The solution was added with sodium cyanoborohydride (54.0 mg) and then adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 16 hours. After the reaction, the solvent was distilled off. A 1 mol/l sodium hydroxide aqueous solution was added to the residue, and chloroform extraction was then carried out. The extract was washed with saturated saline solution and then dried with magnesium sulfate, followed by distilling the solvent off. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (212 mg) as a white solid.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionA 1 mol/l sodium hydroxide aqueous solution was added to the residue, and chloroform extraction
  4. washThe extract was washed with saturated saline solution
  5. dry with materialdried with magnesium sulfate
  6. distillationby distilling the solvent off
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-340ed44733b34eab9bcf85a487ea206e
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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