Pyridine → HCID 137199430, compound

HRID 521709Notes

Reaction equation

HRID 521709 reaction equation
[CH2:1]([N:4]([CH2:12][C:13](=O)[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].Cl.[NH2:22][OH:23].N1C=CC=CC=1>C(O)C>[CH2:1]([N:4]([CH2:12][C:13](=[N:22][OH:23])[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]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 90121155HCID 90121155, compound

Product 1

HCID 137199430HCID 137199430, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl N-allyl-N-(2-oxo-2-pyrazin-2-yl-ethyl)carbamate (6.53 g, 23.55 mmol) is dissolved in ethanol (22 mL) with stirring under nitrogen. Hydroxylamine hydrochloride (3.80 g, 54.16 mmol) and pyridine (2.67 mL, 32.97 mmol) are added and the resulting solution is heated at 80° C. under nitrogen for 80 minutes. The reaction is then cooled to room temperature and is concentrated to a small volume under reduced pressure. Dichloromethane (200 ml) and 1 M aqueous sodium hydroxide (60 ml) are added and the phases are separated. The aqueous phase is re-extracted with dichloromethane (2×200 mL). The combined organic extracts are dried over magnesium sulfate and the solvent is evaporated under reduced pressure. The crude product is purified by silica gel chromatography using a 0-5% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound as a mixture of E/Z isomers (6.61 g, 96%). ES/MS (m/e): 293 (M+1).

Workup

  1. temperatureThe reaction is then cooled to room temperature
  2. concentrationis concentrated to a small volume under reduced pressure
  3. additionDichloromethane (200 ml) and 1 M aqueous sodium hydroxide (60 ml) are added
  4. customthe phases are separated
  5. extractionThe aqueous phase is re-extracted with dichloromethane (2×200 mL)
  6. dry with materialThe combined organic extracts are dried over magnesium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-a5240f847c8f4446b3a94ef05701c356
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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