Sodium Azide → HCID 19892762, compound

HRID 1172561Notes

Reaction equation

HRID 1172561 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]2[CH2:13][CH:14]([CH2:17]OS(C)(=O)=O)[CH2:15][CH2:16][CH:9]2[CH2:8]1.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C.O>[N:23]([CH2:17][CH:14]1[CH2:13][N:10]2[CH2:11][CH2:12][N:7]([C:2]3[N:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:8][CH:9]2[CH2:16][CH2:15]1)=[N+:24]=[N-:25]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 19963213HCID 19963213, compound

Product 1

HCID 19892762HCID 19892762, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution containing methanesulfonic acid 2-pyrimidin-2-yl-octahydro-pyrido[1,2-a]pyrazin-7-ylmethyl ester (1 eq., see subpart (b) above) and sodium azide (2 eq.) in DMF was stirred at around 90° C. for 24 hours. The solution was cooled to room temperature, diluted with water, and extracted with methylene chloride. The combined organic layers was washed with brine, dried over Na2SO4, filtered, and concentrated to give the corresponding azide as yellow oil. This material was used in the next step without further purification.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03abfb97fd874bf68adee553bac09ea3
Source dataset
uspto-grants-2010_11
Patent number
US07834014B2

Reaction notes

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