HCID 22032839, compound → HCID 86587160, compound

HRID 2084264Notes

Reaction equation

HRID 2084264 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](Cl)=[O:11])[CH:2]=1.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[CH:22]=[N:23][NH2:24]>C1COCC1.CCN(CC)CC>[F:17][C:18]([F:28])([F:29])[C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[CH:22]=[N:23][NH:24][C:10]([C:9]1[C:8]([O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:16][CH:15]=[CH:14][CH:13]=1)=[O:11]

Participants

5

Reactant 2

HCID 22032839HCID 22032839, compoundHCID 69356013HCID 69356013, compound

Product 1

HCID 86587160HCID 86587160, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 2-(pyridin-3-yloxy)-nicotinic acid (0.432 g, 2.0 mmol) in THF (15 mL) at 0° C. was added oxalylchloride (2 mL, 2M in CH2Cl2, 4.0 mmol) dropwise. The solution was stirred at room temperature for 3 h. The solvent was evaporated in vacuo to yield 2-(pyridin-3-yloxy)-nicotinoyl chloride as a solid. To a solution of 2-(pyridin-3-yloxy)-nicotinoyl chloride in 15 mL THF was added 3-trifluoromethyl-benzylidene-hydrazine (0.376 g, 2.0 mmol) in 5 mL THF and 1 mL Et3N at 0° C. The reaction mixture was refluxed for 6 h and the solvent was evaporated. The residue was purified by chromatography with EtOAc:hexanes, 1:2, yielding (0.425 g, 55%) of the title compound. 1H NMR (DMSO-d6): 12.20 (s, 1H), 8.70 (s, 1H), 8.37 (s, 1H), 8.24 (s, 1H), 8.21 (d, J=7.8 Hz, 1H), 8.01 (d, J=7.5 Hz, 1H), 7.90 (m, 2H), 7.78 (t, J=7.8 Hz, 1H), 7.41 (m, 2H), 6.43 (m, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customthe solvent was evaporated
  3. customThe residue was purified by chromatography with EtOAc

Sources & evidence

ORD record
ord-ab1c479e2cf04262a0f5e478c2704be0
Source dataset
uspto-grants-2004_04
Patent number
US06716859B2

Reaction notes

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