Ethanol → HCID 12992939, compound

HRID 844233Notes

Reaction equation

HRID 844233 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)=[CH:13][CH:14]=3)[N:9]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH2:27]([OH:29])C>[Pd]>[NH3:9].[CH3:27][OH:29].[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)=[CH:13][CH:14]=3)[N:9]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 702Ethanol2×HCID 15549971HCID 15549971, compound

Product 2

HCID 12992939HCID 12992939, compoundHCID 21705897Ammonia methanol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a 10 mL round bottom flask equipped with a stir bar was added 10% Pd/C (˜10 mg) and ethanol (3 mL). To this stirred suspension was added a solution of the compound of Example 1, above, (0.5 g; 0.13 mmol) in ethanol (2 mL), under argon. The mixture was purged with hydrogen gas in a balloon and stirred at room temperature for 14 h. The reaction mixture was filtered through a pad of celite and the solvent removed in vacuo. The crude residue was purified by column chromatography on silica gel using chloroform:ammonia/methanol (2N) (98:2) to yield the title compound as a yellow oil (0.02 g).

Workup

  1. customIn a 10 mL round bottom flask equipped with a stir bar
  2. customThe mixture was purged with hydrogen gas in a balloon
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. customthe solvent removed in vacuo
  5. customThe crude residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0dc7f6b4b98d437f98f8e603351bf644
Source dataset
uspto-grants-2002_04
Patent number
US06380242B1

Reaction notes

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