Pyridine → HCID 89601899, compound

HRID 570910Notes

Reaction equation

HRID 570910 reaction equation
C([N:4]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:5]1[CH2:10][C:9]([CH:11]=O)=[N:8][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]1=[O:20])(=O)C.N1C=CC=CC=1.Cl.[CH3:35][O:36][NH2:37]>CO>[C:24]([O:23][C:21]([NH:4][N:5]1[CH2:10][C:9](/[CH:11]=[N:37]/[O:36][CH3:35])=[N:8][N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]1=[O:20])=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 89601756HCID 89601756, compound

Product 1

HCID 89601899HCID 89601899, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-[acetyl(tert-butoxycarbonyl)amino]-6-formyl-3-oxo-5H-1,2,4-triazine-2-carboxylate (1.15 g, 3.00 mmol) in MeOH (1.8 mL) at room temperature was added pyridine (0.88 mL, 10.9 mmol) followed by O-methylhydroxylamine HCl salt (376 mg, 4.50 mmol). The obtained mixture was stirred for 20 h at room temperature and then concentrated under reduced pressure. The residual was redissolved in EtOAc, washed with water and dried (Na2SO4). After evaporation of the solvent, the crude product was obtained as a viscous oil which was used in the subsequent step without further purification. LCMS (Method I) RT 1.77 min. [M+H]+ 372.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residual was redissolved in EtOAc
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-b5e991b3b1e74e3ba89573da768cec54
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

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