Sodium Hydroxide → HCID 23155461, compound

HRID 2080827Notes

Reaction equation

HRID 2080827 reaction equation
[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[N:10]([CH:20]([CH3:22])[CH3:21])[C:11]2[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH2:2][CH3:3].[OH-].[Na+]>C(O)C.[Ni]>[NH2:19][CH2:18][C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:23][CH2:24][CH3:25])[N:10]([CH:20]([CH3:21])[CH3:22])[C:11]=2[CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23155459HCID 23155459, compound

Product 1

HCID 23155461HCID 23155461, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The compound (34.0 mg) obtained in Example 47-3 was dissolved in ethanol (2.0 ml) and added with a 1 mol/l sodium hydroxide aqueous solution (340 μl) and Raney nickel (4.0 mg). The whole was stirred overnight at room temperature under a hydrogen atmosphere. After completion of the reaction, the solution was filtrated through Celite and the solvent was distilled off. The resultant was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (31.3 mg) as a pale-yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe solution was filtrated through Celite
  3. distillationthe solvent was distilled off
  4. extractionThe resultant was subjected to extraction with chloroform
  5. washwashed with a saturated saline solution
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-d99526f88bd34b15b81a48ebb7a426cb
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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