Acetic Acid → HCID 11677024, compound

HRID 2080817Notes

Reaction equation

HRID 2080817 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]([CH2:13][N:14]([CH3:25])[CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:11][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:10]=[CH:11][C:12]([CH2:13][N:14]([CH3:25])[CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:26][CH:27]=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 23155419HCID 23155419, compound

Product 1

HCID 11677024HCID 11677024, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (116.3 mg) obtained in Example 44-6 was dissolved in methanol (5.81 ml) and added with 1-methyl-2-imidazole carboxaldehyde (52.0 mg) and sodium cyanoborohydride (39.6 mg). The solution was adjusted to pH 4 with acetic acid and stirred at room temperature for 6 days. The reaction solution was concentrated under reduced pressure. The residue was dissolved in chloroform, washed with a 1 mol/l sodium hydroxide aqueous solution and a saturated saline solution, and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining a hydrochloride (163.4 mg) of the subject compound as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  4. dry with materiala saturated saline solution, and dried with anhydrous sodium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (chloroform/methanol)
  7. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-7aeb6379f4e04fbe92ff1f67c5d2509b
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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