Pyridine → HCID 66998202, compound

HRID 1907881Notes

Reaction equation

HRID 1907881 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]([OH:13])=O)[CH:3]=1.S(Cl)(Cl)=O.N1C=CC=CC=1.[F:24][C:25]([F:34])([F:33])[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([NH2:32])[CH:27]=1>ClCCl.CO.C1COCC1>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]([NH:32][C:28]2[CH:27]=[C:26]([C:25]([F:33])([F:24])[F:34])[CH:31]=[CH:30][N:29]=2)=[O:13])[CH:3]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 27783152-Amino-4-(trifluoromethyl)pyridineHCID 130404024-Amino-5-nitropyridine-2-carboxylic acid

Product 1

HCID 66998202HCID 66998202, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-amino-5-nitropicolinic acid (180 mg, 1.0 mmol) in 10 mL dichloromethane with 280 μL thionyl chloride was refluxed for 1 h, cooled to ambient temperature and concentrated to dryness i. vac. The residue was mixed with 10 mL THF and 10 mL dichloromethane and pyridine (100 μL, 1.3 mmol), and 4-trifluoromethyl-pyridin-2-amine (160 mg, 1.0 mmol) was added to the mixture. After stirring for 45 min the mixture was disturbed with methanol and concentrated i.vac. The residue was purified by chromatography on HPLC (C18 StableBond, eluent: H2O+0.15% HCOOH+10-100% acetonitrile)

Workup

  1. temperaturewas refluxed for 1 h
  2. concentrationconcentrated to dryness i
  3. additionwas added to the mixture
  4. concentrationconcentrated i.vac
  5. customThe residue was purified by chromatography on HPLC (C18 StableBond, eluent: H2O+0.15% HCOOH+10-100% acetonitrile)

Sources & evidence

ORD record
ord-475aeea121bc404f98d623a9906dbe6b
Source dataset
uspto-grants-2013_12
Patent number
US08598190B2

Reaction notes

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