HCID 137199430, compound → HCID 90111971, compound

HRID 521711Notes

Reaction equation

HRID 521711 reaction equation
[CH2:1]([N:4]([CH2:12][C:13](=[N:20][OH:21])[C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3]>C1(C)C=CC=CC=1>[N:15]1[CH:16]=[CH:17][N:18]=[CH:19][C:14]=1[C:13]12[CH2:12][N:4]([C:5]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:11])[CH2:1][CH:2]1[CH2:3][O:21][NH:20]2

Participants

3

Reactant 1

HCID 137199430HCID 137199430, compound

Product 1

HCID 90111971HCID 90111971, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butyl N-allyl-N-(2-hydroxyimino-2-pyrazin-2-yl-ethyl)carbamate (6.6 g, 22.58 mmol) in toluene (80 mL) is stirred at 120° C. for 22 hours. The reaction is cooled and the solvent is evaporated under reduced pressure. The crude product is purified by silica gel column chromatography using a 0-5% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (5.13 g, 74%). ES/MS (m/e): 293 (M+1).

Workup

  1. temperatureThe reaction is cooled
  2. customthe solvent is evaporated under reduced pressure
  3. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e2f6d3f0cf6c407db6ac3c4b032b677b
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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