Acetonitrile → HCID 178517491, compound

HRID 1431329Notes

Reaction equation

HRID 1431329 reaction equation
F[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(#N)C.C(N(C(C)C)CC)(C)C.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29](=[NH:31])[NH2:30]>>[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[N:30]=[C:4]([OH:5])[C:3]2[CH:7]=[CH:8][CH:9]=[N:10][C:2]=2[N:31]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 556504PicolinimidamideHCID 219595822-Fluoropyridine-3-carbonyl chloride

Product 1

HCID 178517491HCID 178517491, compound

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 2-fluoro-3-pyridinecarboxylic acid (6.3 g, 44.6 mmol) in DCM (112 mL) was added thionyl chloride (15.0 mL, 205 mmol). The reaction was heated to 40° C. and stirring continued for 3.5 h. After which, the reaction mixture was concentrated in vacuo to provide 2-fluoronicotinoyl chloride as a yellow solid. The product was taken on crude to the next step. To a stirred solution of 2-fluoronicotinoyl chloride (6.3 g, 39.5 mmol) in acetonitrile (197 mL, 39.5 mmol) was added diisopropylethylamine (27.5 mL, 158 mmol) followed by picolinimidamide (5.26 g, 43.4 mmol). The reaction was heated to 90° C. and stirring continued for 27 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was placed in Et2O (100 mL) and the mixture was filtered and was further washed with Et2O. The product was dried under vacuum and used crude in the next reaction. Mass Spectrum (ESI) m/e=225.1 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. filtrationthe mixture was filtered
  4. washwas further washed with Et2O
  5. customThe product was dried under vacuum
  6. customin the next reaction

Sources & evidence

ORD record
ord-4c4650c73ae549cbafdcc07f029edd4e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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