Dimethylformamide → 3-(Imidazo[1,2-a]pyrazin-3-ylethynyl)-4-methylbenzoic acid

HRID 1622506Notes

Reaction equation

HRID 1622506 reaction equation
[C:1]([C:3]1[N:7]2[CH:8]=[CH:9][N:10]=[CH:11][C:6]2=[N:5][CH:4]=1)#[CH:2].I[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:16]([OH:18])=[O:17].CN(C=O)C.CCN(C(C)C)C(C)C>C(N(CC)CC)C.C(OCC)(=O)C>[N:5]1[CH:4]=[C:3]([C:1]#[C:2][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([OH:18])=[O:17])[N:7]2[CH:8]=[CH:9][N:10]=[CH:11][C:6]=12

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 6216403-Iodo-4-methylbenzoic acidHCID 722072723-Ethynyl-imidazo[1,2-A]pyrazine

Product 1

HCID 667360783-(Imidazo[1,2-a]pyrazin-3-ylethynyl)-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

can be prepared in a manner similar to that described above for the Sonogashira reaction. 3-Ethynylimidazo[1,2-a]pyrazine and 3-iodo-4-methylbenzoic acid are used as coupling partners. Alternatively, the solvent (DMF) can be replaced by ethyl acetate and the base (Hunig base) can be replaced by triethylamine. The product can be isolated by filtration of the crude reaction mixture. The filter cake is washed sequentially with a solvent such as ethyl acetate and then water, then dried in a vacuum oven. Further purification can be achieved by slurrying the solids in water adjusted to pH 3 with the addition of concentrated HCl. After filtration and water wash, the product can be dried in a vacuum oven.

Workup

  1. customcan be prepared in a manner similar to
  2. customthat described above for the Sonogashira reaction
  3. customThe product can be isolated by filtration of the crude
  4. customreaction mixture
  5. washThe filter cake is washed sequentially with a solvent such as ethyl acetate
  6. dry with materialwater, then dried in a vacuum oven
  7. customFurther purification
  8. additionadjusted to pH 3 with the addition of concentrated HCl
  9. filtrationAfter filtration and water
  10. washwash
  11. customthe product can be dried in a vacuum oven

Sources & evidence

ORD record
ord-da52eb31e58442419dee0fe7f9a87ce8
Source dataset
uspto-grants-2014_07
Patent number
US08778942B2

Reaction notes

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