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6-Methylpyridine-2-carboxylic acid → HCID 58268025, compound

HRID 1615975
Notes
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Reaction equation

HRID 1615975 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][C:11]1[N:16]=[C:15]([C:17]([OH:19])=O)[CH:14]=[CH:13][CH:12]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[Br:44][C:45]1[CH:46]=[C:47]([NH2:56])[C:48]2[CH:49]=[N:50][N:51]([CH2:54][CH3:55])[C:52]=2[CH:53]=1>CN(C=O)C>[Br:44][C:45]1[CH:53]=[C:52]2[C:48]([CH:49]=[N:50][N:51]2[CH2:54][CH3:55])=[C:47]([NH:56][C:17]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:10])[N:16]=2)=[O:19])[CH:46]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

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 58268029HCID 58268029, compound

Product 1

HCID 58268025HCID 58268025, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.161 ml, 0.93 mmol) was added to 6-methyl-2-pyridinecarboxylic acid (available from Fluorochem, 51 mg, 0.37 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (174 mg, 0.46 mmol) in DMF (3 ml). The reaction was stirred for 30 mins under nitrogen then 6-bromo-1-ethyl-1H-indazol-4-amine (100 mg, 0.42 mmol) was added and the reaction was stirred overnight. The solvent was evaporated and water (5 ml) was added before extraction into DCM (2×20 ml). The compound was loaded onto an aminopropyl cartridge (20 g), eluted with 10% MeOH in DCM and evaporated to dryness. The residue was purified by silica chromatography, eluting with 0-50% ethyl acetate in DCM over 60 mins. Appropriate fractions were evaporated to give the title compound (107 mg).

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe solvent was evaporated
  3. additionwater (5 ml) was added before extraction into DCM (2×20 ml)
  4. washeluted with 10% MeOH in DCM
  5. customevaporated to dryness
  6. customThe residue was purified by silica chromatography
  7. washeluting with 0-50% ethyl acetate in DCM over 60 mins
  8. customAppropriate fractions were evaporated

Sources & evidence

ORD record
ord-38849e14d40d4dc183551e13d7418a74
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765743B2

Reaction notes

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