Pyridine → HCID 11021867, compound

HRID 1419509Notes

Reaction equation

HRID 1419509 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].N1C=CC=CC=1.[C:14]([NH:18][C:19]([C:21]1[N:22]([C:27](=[O:29])[CH3:28])[CH2:23][CH2:24][NH:25][CH:26]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15].[OH-].[Na+]>O>[C:14]([NH:18][C:19]([C:21]1[N:22]([C:27](=[O:29])[CH3:28])[CH2:23][CH2:24][N:25]([C:1](=[O:3])[CH3:2])[CH:26]=1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 15508343HCID 15508343, compound

Product 1

HCID 11021867HCID 11021867, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

16.7 g (163 mmol) of acetic anhydride and 12.4 g (157 mmol) of pyridine were added to 20.00 g (88.8 mmol) of 1-acetyl-1,4,5,6-tetrahydropyrazine-2-carboxylic acid tert-butylamide and the mixture was stirred for 4 hours at 25° C. 100 ml of water was then added and the pH was adjusted to 6 with 30 ml of sodium hydroxide solution (20%). Extraction was then carried out by shaking with three times 100 ml of methyl ethyl ketone. The combined organic extracts were dried over magnesium sulfate, toluene was added and the mixture was concentrated. The vigorously foaming crude product crystallized and 11.40 g (48%) of the title compound was isolated in the form of a light brown solid. The melting point of the title compound was: 138.0° to 139.2° C. Other data concerning the title compound was:

Workup

  1. extractionExtraction
  2. stirringby shaking with three times 100 ml of methyl ethyl ketone
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate, toluene
  4. additionwas added
  5. concentrationthe mixture was concentrated
  6. customcrystallized

Sources & evidence

ORD record
ord-0b8b10924aa0455fa62d509a6e1a168d
Source dataset
uspto-grants-1999_03
Patent number
US05886181

Reaction notes

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