HCID 57563580, compound → HCID 23016844, compound

HRID 1726328Notes

Reaction equation

HRID 1726328 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[CH:8][C:7]=1[C:18]#[C:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO.[C].[Pd]>[C:23]1([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:7]2[CH:8]=[C:9]([CH2:12][N:13]3[CH:17]=[CH:16][CH:15]=[N:14]3)[CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][C:3]([OH:29])=[O:2])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 57563580HCID 57563580, compound

Product 1

HCID 23016844HCID 23016844, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of the compound prepared in Example 36 (300 mg) in methanol (3 ml) was added 10% palladium carbon (30 mg) and the mixture was stirred at room temperature overnight under an atmosphere of hydrogen. The reaction mixture was filtered through cellite (trade mark) and then the filtrate was concentrated. To a solution of the residue in THF were added 1N aqueous solution of sodium hydroxide (2 ml) and methanol (2 ml) and the mixture was stirred at room temperature overnight. The reaction solution was neutralized with 1N hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel to give the title compound (220 mg) having the following physical data.

Workup

  1. filtrationThe reaction mixture was filtered through cellite (trade mark)
  2. concentrationthe filtrate was concentrated
  3. additionTo a solution of the residue in THF were added 1N aqueous solution of sodium hydroxide (2 ml) and methanol (2 ml)
  4. stirringthe mixture was stirred at room temperature overnight
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f40c83f753824bff9546a168018ea4b6
Source dataset
uspto-grants-2009_02
Patent number
US07491748B2

Reaction notes

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