Sodium Azide → 4-(2-azidoethyl)-7-iodo-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one

HRID 711400Notes

Reaction equation

HRID 711400 reaction equation
CS(O[CH2:6][CH2:7][CH:8]1[N:13]2[CH:14]=[C:15]([I:17])[CH:16]=[C:12]2[C:11](=[O:18])[NH:10][CH2:9]1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+]>C(#N)C.CN(C=O)C>[N:19]([CH2:6][CH2:7][CH:8]1[N:13]2[CH:14]=[C:15]([I:17])[CH:16]=[C:12]2[C:11](=[O:18])[NH:10][CH2:9]1)=[N+:20]=[N-:21]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 867325512-(7-Iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)ethyl methanesulfonate

Product 1

HCID 867325524-(2-azidoethyl)-7-iodo-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-oneYield 76.9%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

2-(7-iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)ethyl methanesulfonate (0.150 g, 0.39 mmol) was reacted with sodium azide (0.076 g, 1.17 mmol) in ACN/DMF (4 ml, 1:1 ratio) for 4 hours at 80° C. under N2. The solvents were removed under vacuum, the residue was partitioned between water and DCM. The organic phase was dried (Na2SO4), filtered and evaporated, yielding the title compound as a white solid (0.097 g, 0.30 mmol, 75%).

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue was partitioned between water and DCM
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-2e5e7dfba6f242b5a3a7ea5b5d1df8e5
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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