Trimethyl orthoformate → HCID 67103600, compound

HRID 2080824Notes

Reaction equation

HRID 2080824 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][CH2:12][CH2:13][N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[N:8]([CH2:21][CH2:22][CH3:23])[C:7]=2[CH:24]=1.[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O.C(OC)(OC)OC.[BH4-].[Na+]>CO>[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH2:30][NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][CH2:12][CH2:13][N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[N:8]([CH2:21][CH2:22][CH3:23])[C:7]=2[CH:24]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 23155492HCID 23155492, compound

Product 1

HCID 67103600HCID 67103600, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An anhydrous methanol solution (4.0 ml) containing the compound (0.244 g) obtained in Example 46-6 and 2-imidazole carboxaldehyde (85.0 mg) was added with trimethyl orthoformate (0.242 ml). The whole was stirred at room temperature for 14 hours and then added with sodium borohydride (0.140 g). After the solution was stirred for 2 hours, the solvent was distilled off. The resultant was dissolved in chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution, and dried with anhydrous magnesium sulfate. The residue obtained by distilling the solvent off was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (0.167 g) as a colorless oily substance.

Workup

  1. stirringAfter the solution was stirred for 2 hours
  2. distillationthe solvent was distilled off
  3. dissolutionThe resultant was dissolved in chloroform
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe residue obtained
  7. distillationby distilling the solvent
  8. customoff was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-9f644f1025604799a79118200ac4a685
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

Loading…