Acetic Acid → HCID 58345806, compound

HRID 2080848Notes

Reaction equation

HRID 2080848 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:30]=[CH:29][C:12]2[N:13]=[C:14]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[N:15]([CH2:16][CH2:17][CH3:18])[C:11]=2[CH:10]=1.[CH3:31][N:32]1[CH:36]=[CH:35][N:34]=[C:33]1[CH:37]=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[CH2:6][N:7]([CH2:37][C:33]1[N:32]([CH3:31])[CH:36]=[CH:35][N:34]=1)[CH2:8][C:9]1[CH:30]=[CH:29][C:12]2[N:13]=[C:14]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[N:15]([CH2:16][CH2:17][CH3:18])[C:11]=2[CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23155584HCID 23155584, compound

Product 1

HCID 58345806HCID 58345806, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (429.5 mg) obtained in Example 61-4 was dissolved in methanol (21.5 ml) and added with 1-methyl-2-imidazole carboxaldehyde (173.6 mg) and sodium cyanoborohydride (132.1 mg). After the solution was adjusted to pH 4 with acetic acid, the whole was stirred at room temperature for 4 days. The reaction solution was concentrated under reduced pressure. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution and a saturated saline solution. Then, the resultant was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining a hydrochloride (559.2 mg) of the subject compound as a pale-yellow 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 materialThen, the resultant was dried with anhydrous sodium sulfate
  5. concentrationconcentrated 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-ffd7beee259b47aebbd860e685118eb3
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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