Trimethylsilyldiazomethane → HCID 59139878, compound

HRID 1799475Notes

Reaction equation

HRID 1799475 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14]([OH:16])=[O:15])=[N:10][N:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=3)[C:8]2=[O:27])=[CH:4][CH:3]=1.[CH3:30][Si](C=[N+]=[N-])(C)C>CO.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([C:14]([O:16][CH3:30])=[O:15])=[N:10][N:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=3)[C:8]2=[O:27])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 68699892HCID 68699892, compound

Product 1

HCID 59139878HCID 59139878, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

According to Scheme 7 Step 5: To a solution of 2-(3-acetamidophenyl)-4-(4-chlorobenzyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid 11(D) (80 mg, 0.19 mmol) in MeOH (3 mL) was added dropwise at 0° C. a solution of trimethylsilyldiazomethane 2M (1.3 mL, 2.70 mmol). The mixture was stirred at room temperature for 18 h. The mixture was diluted with 100 mL of a saturated solution of NaHCO3 and the aqueous layer was extracted twice with 100 mL of DCM. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford a yellow solid. The crude solid was purified by flash chromatography with silica gel (AIT Flashmart prepacked column 7 g SiO2) using CH2Cl2/MeOH 98/2 as eluant to afford a yellow solid. The solid was further triturated with diisopropylether and filtered to afford methyl 4-(4-chlorobenzyl)-2-(3-acetamidophenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylate (35 mg, 42%) as a beige solid.

Workup

  1. extractionthe aqueous layer was extracted twice with 100 mL of DCM
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford a yellow solid
  6. customThe crude solid was purified by flash chromatography with silica gel (AIT Flashmart prepacked column 7 g SiO2)
  7. customto afford a yellow solid
  8. customThe solid was further triturated with diisopropylether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-0befee303bb446cebc9205a373a706aa
Source dataset
uspto-grants-2013_01
Patent number
US08344138B2

Reaction notes

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