Triethylamine → HCID 117987874, compound

HRID 2206255Notes

Reaction equation

HRID 2206255 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]([OH:12])=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.Cl.Cl.[CH3:47][C:48]1([CH3:55])[CH2:52][CH2:51][CH2:50][CH:49]1[NH:53][NH2:54]>CC(N(C)C)=O.O>[CH3:47][C:48]1([CH3:55])[CH2:52][CH2:51][CH2:50][CH:49]1[NH:53][NH:54][C:10](=[O:12])[C:3]1[C:2]([I:1])=[CH:7][CH:6]=[N:5][C:4]=1[O:8][CH3:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 184399404-Iodo-2-methoxypyridine-3-carboxylic acidHCID 131735844HCID 131735844, compound

Product 1

HCID 117987874HCID 117987874, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a mixture of 4-iodo-2-methoxy-3-pyridinecarboxylic acid (2.8 g) and triethylamine (4.5 g) in DMA (40 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (5.7 g) under ice-cooling. The reaction mixture was stirred at room temperature for 30 min, and (2,2-dimethylcyclopentyl)hydrazine trihydrochloride (2.8 g) was added thereto under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr, and added to water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give the title compound (3.0 g).

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringThe reaction mixture was stirred at room temperature for 1 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-1eebf3e8385a4c1b84b8004204e94263
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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