2-Pyrazinecarboxylic acid → HCID 44251588, compound

HRID 2359388Notes

Reaction equation

HRID 2359388 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[C:10]([NH2:17])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[C:24](O)=[O:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[C:10]([NH:17][C:24]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][N:18]=4)=[O:25])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 199558612-Phenylquinolin-8-amine

Product 1

HCID 44251588HCID 44251588, compoundYield 11.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Phenylquinolin-8-amine (60 mg, 0.27 mmol) was taken up in 2 mL of DMF along with pyrazine-2-carboxylic acid (34 mg, 0.27 mmol), HATU (207 mg, 0.54 mmol) and DIEA (95 μL, 0.54 mmol). The reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc and washed with water. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by preparative HPLC (using aqueous CH3CN that has been buffered with 0.1% TFA) to afford 10 mg of the product. MS (ESI) calcd for C20H14N4O (m/z): 326.12. found: 327 [M+1].

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by preparative HPLC (using aqueous CH3CN that has been buffered with 0.1% TFA)

Sources & evidence

ORD record
ord-0dbe8934bb77407fbf01b0aaefe415e3
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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