Acetic Acid → HCID 10368369, compound

HRID 2080765Notes

Reaction equation

HRID 2080765 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH2:13][CH2:12]2.[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>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH3:29])[CH2:13][CH2:12]2)[CH2:36][C:32]1[N:31]([CH3:30])[CH:35]=[CH:34][N:33]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23155462HCID 23155462, compound

Product 1

HCID 10368369HCID 10368369, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (104 mg) obtained in Example 17-7 was dissolved in anhydrous methanol (4.0 ml) and added with 1-methyl-2-imidazole carboxaldehyde (42.9 mg) and sodium cyanoborohydride (49.0 mg). The solution was adjusted to pH 5 with acetic acid and stirred at room temperature for 16.5 hours. After completion of the reaction, the solvent was distilled off. The resultant was added with a 1 mol/l sodium hydroxide aqueous solution, subjected to extraction with chloroform, and dried with magnesium sulfate. 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 (115 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 materialdried 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-cc8e6cdb4a374f2c899414bf5897463e
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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