Water → HCID 22179392, compound

HRID 1016257Notes

Reaction equation

HRID 1016257 reaction equation
[C:1]1([CH3:30])[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][NH:9][C:10]2[C:11](=[O:29])[N:12]([CH2:18][C:19]([O:21]CC3C=CC=CC=3)=[O:20])[C:13]([CH3:17])=[C:14](Cl)[N:15]=2)=[CH:3][CH:2]=1.[OH-].[K+].O>[Pd].O1CCCC1.CO>[C:1]1([CH3:30])[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][NH:9][C:10]2[C:11](=[O:29])[N:12]([CH2:18][C:19]([OH:21])=[O:20])[C:13]([CH3:17])=[CH:14][N:15]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 22179411HCID 22179411, compound

Product 1

HCID 22179392HCID 22179392, compoundYield 22.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(2-4-tolylethylamino)-5-chloro-6-methyl-1-(benzyloxycarbonylmethyl)pyrazinone (854 mg, 2.00 mmol), as prepared in the preceding step, potassium hydroxide (452 mg, 8.00 mmol), 10% palladium on carbon (254 mg) in tetrahydrofuran (20 mL), methanol (30 mL), and water (7 mL) was stirred under hydrogen balloon for three days. The mixture was filtered through Celite. The filtrate was adjusted to pH 2-4 with 10% HCl and concentrated to about 2 mL under reduced pressure. The white solid which precipitated from the solution was filtered, washed with a small amount of water, and dried to give the title compound (137 mg, 22.7%). 1H NMR (CDCl3) δ 7.20 (d, 2H, J=7.5 Hz), 7.10 (d, 2H, J=7.8 Hz), 6.70 (s, H), 4.71 (s, 2H), 2.87 (m, 2H), 2.50 (m, 2H), 2.26 (s, 3H), 2.15 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated to about 2 mL under reduced pressure
  3. customThe white solid which precipitated from the solution
  4. filtrationwas filtered
  5. washwashed with a small amount of water
  6. customdried

Sources & evidence

ORD record
ord-282e455c37894cc08cfc65964fcb928b
Source dataset
uspto-grants-2002_11
Patent number
US06476016B2

Reaction notes

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