Sodium Hydroxide → HCID 23155584, compound

HRID 2080847Notes

Reaction equation

HRID 2080847 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[N:12]([CH2:22][CH2:23][CH3:24])[C:13]3[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C.[Ni]>[NH:12]1[CH:13]=[CH:14][N:15]=[C:11]1[CH2:10][NH:21][CH2:20][C:18]1[CH:17]=[CH:16][C:14]2[N:15]=[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[N:12]([CH2:22][CH2:23][CH3:24])[C:13]=2[CH:19]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23155521HCID 23155521, compound

Product 1

HCID 23155584HCID 23155584, compoundYield 151%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The compound (451.8 mg) obtained in Example 61-3 was dissolved in ethanol (18.1 ml) and added with a 1 mol/l sodium hydroxide aqueous solution (4.52 ml) and Raney nickel. The whole was stirred at room temperature for 20 hours under a hydrogen atmosphere. The reaction solution was filtrated through Celite and the filtrate was concentrated under reduced pressure. The residue was added with water and the whole was subjected to separation/extraction with chloroform. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was again dissolved in methanol (22.1 ml) and added with 2-imidazole carboxaldehyde (194.0 mg) and trimethyl orthoformate (0.442 ml). The whole was stirred at room temperature for 1.5 hours. Subsequently, the solution was added with sodium borohydride (152.8 mg) 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 separation/extraction with chloroform. The organic layer 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 (429.5 mg) as a yellow oily substance.

Workup

  1. filtrationThe reaction solution was filtrated through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was added with water
  4. extractionthe whole was subjected to separation/extraction with chloroform
  5. washThe organic layer was washed with a saturated saline solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationfollowed by concentration under reduced pressure
  8. dissolutionThe residue was again dissolved in methanol (22.1 ml)
  9. additionadded with 2-imidazole carboxaldehyde (194.0 mg) and trimethyl orthoformate (0.442 ml)
  10. stirringThe whole was stirred at room temperature for 1.5 hours
  11. additionSubsequently, the solution was added with sodium borohydride (152.8 mg) under ice-
  12. temperaturecooling
  13. stirringthe whole was stirred at room temperature for additional 30 minutes
  14. concentrationThe reaction solution was concentrated under reduced pressure
  15. additionThe residue was added with water
  16. extractionthe whole was subjected to separation/extraction with chloroform
  17. washThe organic layer washed with a saturated saline solution
  18. dry with materialdried with anhydrous sodium sulfate
  19. concentrationfollowed by concentration under reduced pressure
  20. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-95c18b00acb54ad6a9355be7758a121d
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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