1,3-Propanediamine → N1-(6-Bromo-3-iodoimidazo[1,2-a]pyrazin-8-yl)propane-1,3-diamine

HRID 1498612Notes

Reaction equation

HRID 1498612 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][NH2:4].[Br:6][C:7]1[N:8]=[C:9](S(C)(=O)=O)[C:10]2[N:11]([C:13]([I:16])=[CH:14][N:15]=2)[CH:12]=1>CN(C)C=O>[Br:6][C:7]1[N:8]=[C:9]([NH:4][CH2:3][CH2:2][CH2:1][NH2:5])[C:10]2[N:11]([C:13]([I:16])=[CH:14][N:15]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 715340426-Bromo-3-iodo-8-(methylsulfonyl)imidazo[1,2-a]pyrazine

Product 1

HCID 86692024N1-(6-Bromo-3-iodoimidazo[1,2-a]pyrazin-8-yl)propane-1,3-diamineYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 1.26 mL propane-1,3-diamine in 8 mL 2.0 g N,N-dimethylformamide was added a solution of (4.98 mmol) 6-bromo-3-iodo-8-(methylsulfonyl)imidazo[1,2-a]pyrazine which was prepared according to intermediate example 60c in 20 mL N,N-dimethylformamide at 40° C. during 1.5 hours. The mixture was stirred at 40° C. for additional 1.5 hours. The solvent was removed and the residue was purified by chromatography to give 1.52 g (77%) of the title compound.

Workup

  1. customwas prepared
  2. customThe solvent was removed
  3. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-b4866aa3ceaf4775933c53aa352ed496
Source dataset
uspto-grants-2015_12
Patent number
US09199999B2

Reaction notes

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