Water → 6-Bromo-3-iodo-N-isobutylimidazo[1,2-a]pyrazin-8-amine

HRID 925588Notes

Reaction equation

HRID 925588 reaction equation
[Br:1][C:2]1[N:3]=[C:4](S(C)(=O)=O)[C:5]2[N:6]([C:8]([I:11])=[CH:9][N:10]=2)[CH:7]=1.[CH2:16]([NH2:20])[CH:17]([CH3:19])[CH3:18].O>CN1C(=O)CCC1>[Br:1][C:2]1[N:3]=[C:4]([NH:20][CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]2[N:6]([C:8]([I:11])=[CH:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6558IsobutylamineHCID 715340426-Bromo-3-iodo-8-(methylsulfonyl)imidazo[1,2-a]pyrazine

Product 1

HCID 715340446-Bromo-3-iodo-N-isobutylimidazo[1,2-a]pyrazin-8-amineYield 77.52%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of 6-bromo-3-iodo-8-methanesulfonyl-imidazo[1,2-a]pyrazine (5.08 g, 12.64 mmol) in NMP (100 mL) was added 3.77 mL isobutylamine (2.77 g, 37.90 mmol, 3 eq) in one portion at rt. After stirring for 2 h at rt, 500 mL water was added and the mixture was extracted with ethyl acetate (3×200 mL). The organic phase was filtered, evaporated and the residue was recrystallized from MeOH/water to yield 3.87 g (77.52%) (6-bromo-3-iodo-imidazo[1,2-a]pyrazin-8-yl)-isobutyl-amine: 1H-NMR (300 MHz, d6-DMSO): δ=8.09 (1H, tr), 7.60 (1H, s), 7.54 (1H, s), 3.19 (2H, dd), 1.95 (1H, m), 0.85 (6H, d) ppm.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×200 mL)
  2. filtrationThe organic phase was filtered
  3. customevaporated
  4. customthe residue was recrystallized from MeOH/water

Sources & evidence

ORD record
ord-fb1db4f3956343f1accf8cd96197d578
Source dataset
uspto-grants-2016_03
Patent number
US09284317B2

Reaction notes

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