Acetic Acid → HCID 10028065, compound

HRID 348730Notes

Reaction equation

HRID 348730 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:27]=[CH:26][C:12]2[S:13][C:14]([CH2:16][CH2:17][CH2:18][N:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])=[CH:15][C:11]=2[CH:10]=1.[CH3:28][N:29]1[CH:33]=[CH:32][N:31]=[C:30]1[CH:34]=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:27]=[CH:26][C:12]2[S:13][C:14]([CH2:16][CH2:17][CH2:18][N:19]([CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH3:25])=[CH:15][C:11]=2[CH:10]=1)[CH2:34][C:30]1[N:29]([CH3:28])[CH:33]=[CH:32][N:31]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21084400HCID 21084400, compound

Product 1

HCID 10028065HCID 10028065, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (197.9 mg) obtained in Example 120-6 was dissolved in methanol (10 ml) and then added with 1-methyl-2-imidazole carboxaldehyde (68.0 mg) and sodium cyanoborohydride (64.7 mg). After that, the solution was adjusted to pH 5 with acetic acid, followed by stirring overnight at room temperature. After the solvent had been distilled off, the residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (228.7 mg) of the subject compound as a white solid.

Workup

  1. distillationAfter the solvent had been distilled off
  2. customthe residue was purified through silica gel column chromatography (chloroform/methanol)
  3. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-680f357986a24654a4ae786631544810
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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