Dimethylformamide → 5,6,7,8-Tetrahydro-2-(2-methoxy-4-methylsulfonylphenyl)imidazo[1,2-a]pyrazine dihydrochloride

HRID 483083Notes

Reaction equation

HRID 483083 reaction equation
Br.[Cl:2][C:3]1[C:4]2[N:5]([CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][C:13]=3[O:22][CH3:23])[N:11]=2)[CH:6]=[CH:7][N:8]=1.CN(C)C=O>[Pd].C(N(CC)CC)C>[ClH:2].[ClH:2].[CH3:23][O:22][C:13]1[CH:14]=[C:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:16]=[CH:17][C:12]=1[C:10]1[N:11]=[C:4]2[CH2:3][NH:8][CH2:7][CH2:6][N:5]2[CH:9]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 135780278-Chloro-2-(2-methoxy-4-methylsulfonylphenyl)imidazo[1,2-a]pyrazine hydrobromide

Product 1

HCID 201990495,6,7,8-Tetrahydro-2-(2-methoxy-4-methylsulfonylphenyl)imidazo[1,2-a]pyrazine dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A suspension of 4.5 g. of 8-chloro-2-(2-methoxy-4-methylsulfonylphenyl)imidazo[1,2-a]pyrazine hydrobromide in 190 ml. of dimethylformamide was treated with 3.4 g. of triethylamine and 1 g. of 5% palladium-on-carbon. This mixture was hydrogenated at room temperature at 60 psi for about 75 minutes. The catalyst was removed by filtration and the solvent was removed in vacuo. During the course of solvent removal a precipitate occurred which was removed by filtration. The precipitate was triturated with chloroform and the residue was suspended in methanolic hydrogen chloride. After stirring for a period of time, the methanol was removed by evaporation and the resulting solid was collected with acetone by filtration affording 2.1 g. of the desired title product, M+ =307.

Workup

  1. additionA suspension of 4.5 g
  2. customThe catalyst was removed by filtration
  3. customthe solvent was removed in vacuo
  4. customDuring the course of solvent removal a precipitate
  5. customwas removed by filtration
  6. customThe precipitate was triturated with chloroform
  7. customthe methanol was removed by evaporation
  8. filtrationthe resulting solid was collected with acetone by filtration
  9. customaffording 2.1 g

Sources & evidence

ORD record
ord-85b58babf2df4945a1a002652808ef7c
Source dataset
uspto-grants-1986_03
Patent number
US04578387

Reaction notes

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