Trimethyl orthoformate → HCID 23155419, compound

HRID 2080816Notes

Reaction equation

HRID 2080816 reaction equation
[NH2:1][CH2:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]([CH3:19])[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.[NH:22]1[CH:26]=[CH:25][N:24]=[C:23]1[CH:27]=O.C(OC)(OC)OC.[BH4-].[Na+]>CO>[NH:22]1[CH:26]=[CH:25][N:24]=[C:23]1[CH2:27][NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH3:19])[CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 23155570HCID 23155570, compound

Product 1

HCID 23155419HCID 23155419, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (248.5 mg) obtained in Example 44-5 was dissolved in methanol (12.4 ml) and added with 2-imidazole carboxaldehyde (123.7 mg) and trimethyl orthoformate (0.282 ml) and the whole was stirred at room temperature for 2.5 hours. Subsequently, sodium borohydride (97.4 mg) was added thereto under ice-cooling and the whole was stirred at room temperature for additional 30 minutes. The reaction solution was concentrated under reduced pressure. The residue was added with water and the whole was subjected to extraction with chloroform. The organic layer was washed with 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), thereby obtaining the subject compound (116.3 mg) as a yellow oily substance.

Workup

  1. temperatureunder ice-cooling
  2. stirringthe whole was stirred at room temperature for additional 30 minutes
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionThe residue was added with water
  5. extractionthe whole was subjected to extraction with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationfollowed by concentration under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-dba4d6a3b6744fc3ad2c29a2da0d02d8
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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