Acetic Acid → HCID 11599263, compound

HRID 2080800Notes

Reaction equation

HRID 2080800 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][N:6]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][CH2:16][C:17]2[NH:18][CH:19]=[CH:20][N:21]=2)=[CH:10][CH:9]=1.C([BH3-])#N.[Na+].C(O)(=O)C.[CH3:42][N:43]1[CH:47]=[CH:46][N:45]=[C:44]1[CH:48]=O>CO>[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][N:6]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:27][CH2:28][CH3:29])[CH2:30][CH2:31][CH3:32])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][N:15]([CH2:16][C:17]2[NH:18][CH:19]=[CH:20][N:21]=2)[CH2:48][C:44]2[N:43]([CH3:42])[CH:47]=[CH:46][N:45]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67103741HCID 67103741, compound

Product 1

HCID 11599263HCID 11599263, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (48.2 mg) obtained in Example 34-2 was dissolved in anhydrous methanol (1.0 ml) and added with sodium cyanoborohydride (9.90 mg), acetic acid (100 μl), and 1-methyl-2-imidazole carboxaldehyde (12.8 mg) and the whole was stirred at room temperature for 3 days under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off. The resultant was dissolved in chloroform and added with a 1 mol/l sodium hydroxide aqueous solution, and the whole was stirred for a while. The solution was subjected to extraction with chloroform, and washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution. The organic layer was dried with anhydrous sodium 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 (56.1 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThe resultant was dissolved in chloroform
  4. additionadded with a 1 mol/l sodium hydroxide aqueous solution
  5. stirringthe whole was stirred for a while
  6. extractionThe solution was subjected to extraction with chloroform
  7. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  11. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-d35de0e27a3845e5adb935d104ed367f
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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