Acetic Acid → HCID 11755719, compound

HRID 348680Notes

Reaction equation

HRID 348680 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:31]=[CH:30][C:12]([CH2:13][O:14][CH2:15][C:16]2[CH:29]=[CH:28][C:19]([CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1.C([BH3-])#N.[Na+].C(O)(=O)C.[NH:40]1[CH:44]=[CH:43][N:42]=[C:41]1[CH:45]=O>CO>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:8][C:9]1[CH:31]=[CH:30][C:12]([CH2:13][O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][N:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[CH:28][CH:29]=2)=[CH:11][CH:10]=1)[CH2:45][C:41]1[NH:40][CH:44]=[CH:43][N:42]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21084429HCID 21084429, compound

Product 1

HCID 11755719HCID 11755719, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The compound (136 mg) obtained in Example 80-4 was dissolved in anhydrous methanol (3.0 ml) and then added with sodium cyanoborohydride (40.6 mg), acetic acid (1.00 ml), and 2-imidazole carboxaldehyde (46.6 mg), followed by stirring under a nitrogen atmosphere at 60° C. overnight. After completion of the reaction, the solvent was distilled off. Subsequently, the residue was purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (109 mg) of the subject compound as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. customSubsequently, the residue was purified through silica gel column chromatography (chloroform/methanol)
  4. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-25816f8d63974faf83ae5d0befb3841b
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

Loading…