Acetic Acid → HCID 11684903, compound

HRID 2080801Notes

Reaction equation

HRID 2080801 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)=[S: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)=[S:11])[CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23155561HCID 23155561, compound

Product 1

HCID 11684903HCID 11684903, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (93.8 mg) obtained in Example 35-2 was dissolved in anhydrous methanol (3.8 ml) and added with 1-methyl-2-imidazole carboxaldehyde (38.5 mg) and sodium cyanoborohydride (43.4 mg). The solution was adjusted to pH 5 with acetic acid and stirred at room temperature for 13.5 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 the whole was subjected to extraction with chloroform. The resultant was dried with magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (86.6 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. extractionthe whole was subjected to extraction with chloroform
  5. dry with materialThe resultant was dried with magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  8. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-412d07e84c21403ab41f7146857a7c9f
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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