6-Methylpyridine-2-carboxylic acid → HCID 58268015, compound

HRID 1615985Notes

Reaction equation

HRID 1615985 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.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.[Br:44][C:45]1[CH:46]=[C:47]([NH2:55])[C:48]2[CH:49]=[N:50][N:51]([CH3:54])[C:52]=2[CH:53]=1>CN(C=O)C.O>[Br:44][C:45]1[CH:53]=[C:52]2[C:48]([CH:49]=[N:50][N:51]2[CH3:54])=[C:47]([NH:55][C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)=[O:10])[CH:46]=1

Participants

7

Reactant 4

HCID 702826-Methylpyridine-2-carboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58255771HCID 58255771, compound

Product 1

HCID 58268015HCID 58268015, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-Methyl-2-pyridinecarboxylic acid (74 mg, 0.54 mmol) and HATU (250 mg, 0.65 mmol) were dissolved in DMF (4 ml) and then DIPEA (0.23 ml) was then added. The mixture was stirred under nitrogen for 30 min. 6-bromo-1-methyl-1H-indazol-4-amine (135 mg, 0.60 mmol) was then added and stirring was continued under nitrogen overnight. Addition of water was followed by extraction of the resultant mixture with DCM (2×10 ml). The organics were combined and concentrated in vacuo then the residue was purified by chromatography on silica eluting with a gradient of 0-100% ethyl acetate in DCM. Fractions containing desired material were combined and concentrated in vacuo to afford the title compound (120 mg).

Workup

  1. stirringstirring
  2. waitwas continued under nitrogen overnight
  3. extractionwas followed by extraction of the resultant mixture with DCM (2×10 ml)
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by chromatography on silica eluting with a gradient of 0-100% ethyl acetate in DCM
  6. additionFractions containing desired material
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-111ce5fd2ca44b33bdefc8847ceb860a
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

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