N-Acetyl-L-Cysteine → Palladium

HRID 1913380Notes

Reaction equation

HRID 1913380 reaction equation
[C:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=NC#N)[C:12]23[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=1)#[N:2].[Pd:26].[OH-].[K+].C(N[C@H](C(O)=O)CS)(=O)C>C1COCC1>[C:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]=[CH:13][C:12]23[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:5][CH:4]=1)#[N:2].[Pd:26]

Participants

7

Reactant 4

HCID 12035N-Acetyl-L-CysteineHCID 14797Potassium HydroxideHCID 23938PalladiumHCID 178480854HCID 178480854, compound

Product 2

HCID 23938PalladiumHCID 86601519HCID 86601519, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 5′-(5-cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide (1.0 g) containing residual Pd (5100 ppm) was suspended in THF (5 mL). Upon addition of aqueous 1M KOH (5 mL), a clear orange solution was obtained. N-Acetylcysteine (1.3 g) was added, the mixture was stirred for 1 hour, and filtered. Ten percent aqueous HCl (3 mL) was added dropwise to the filtrate causing precipitation of a white solid. The solution was filtered, the solid washed with methanol, and the washed solid dried to give 5′-(5-cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol])-2′-ylidenecyanamide (0.6 g; 60% yield; 96 ppm Pd).

Workup

  1. customa clear orange solution was obtained
  2. filtrationfiltered
  3. additionTen percent aqueous HCl (3 mL) was added dropwise to the filtrate
  4. customprecipitation of a white solid
  5. filtrationThe solution was filtered
  6. washthe solid washed with methanol
  7. customthe washed solid dried

Sources & evidence

ORD record
ord-0ac0b95b14364d5897628fca810edbdb
Source dataset
uspto-grants-2013_12
Patent number
US08609712B2

Reaction notes

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