6-Methylpyridine-2-carboxylic acid → HCID 18449227, compound

HRID 1270156Notes

Reaction equation

HRID 1270156 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([NH:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:8]3[N:9]2[C:12](=[O:15])[NH:13][N:14]=3)=[CH:4][CH:3]=1.[CH3:23][C:24]1[N:29]=[C:28]([C:30](O)=[O:31])[CH:27]=[CH:26][CH:25]=1.C1C=CC2N(O)N=NC=2C=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C=O)C.O.CO.CCOC(C)=O.C(Cl)CCl.C(N(CC)CC)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([NH:16][CH:17]3[CH2:22][CH2:21][N:20]([C:30]([C:28]4[CH:27]=[CH:26][CH:25]=[C:24]([CH3:23])[N:29]=4)=[O:31])[CH2:19][CH2:18]3)[C:8]3[N:9]2[C:12](=[O:15])[NH:13][N:14]=3)=[CH:4][CH:3]=1

Participants

10

Reactant 4

HCID 702826-Methylpyridine-2-carboxylic acid2×HCID 757711-HydroxybenzotriazoleHCID 2724699PyBOPHCID 10017782HCID 10017782, compound

Product 1

HCID 18449227HCID 18449227, compound

Reagents, catalysts & solvents 5

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To a slurry of 98 mg of 8-fluoro-4-(piperidin-4-ylamino)-2H-[1,2,4]triazolo[4,3-a]quinoxalin-1-one, 33 mg of 6-methyl-picolinic acid, and 32 mg of HOBT in DMF (1.4 mL) was added 109 mg of triethylamine, followed by 47 mg of EDC and the mixture was stirred for 18 hrs. To this mixture was added 15 mg of 6-methyl-picolinic acid and 57 mg of benzotriazol-1-yl-oxy-trispyrrolidinophosphonium hexafluorophosphate, and stirring was continued for 30 min. The reaction mixture was diluted with water, and extracted with methylene chloride, and the organic extracts were washed with 50% saturated sodium bicarbonate and water, and then concentrated. The residue was separated using silica gel chromatography to provide a material that was dissolved in 10% MeOH/EtOAc, and washed with water. The organic extract was dried over sodium sulfate, filtered, and concentrated to provide the title compound as a white solid. MS (M+H)+=422.0.

Workup

  1. stirringstirring
  2. waitwas continued for 30 min
  3. extractionextracted with methylene chloride
  4. washthe organic extracts were washed with 50% saturated sodium bicarbonate and water
  5. concentrationconcentrated
  6. customThe residue was separated
  7. customto provide a material that
  8. washwashed with water
  9. extractionThe organic extract
  10. dry with materialwas dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-2db455a6064b4ac39700fe60fcf00eaa
Source dataset
uspto-grants-2007_04
Patent number
US07202245B2

Reaction notes

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