Pyridine → HCID 57974630, compound

HRID 1864640Notes

Reaction equation

HRID 1864640 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1.[NH2:19][C:20]1[C:25]([NH2:26])=[C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:40])[C:36]([F:39])([F:38])[F:37])=[C:30]([F:41])[CH:29]=2)[CH:23]=[CH:22][N:21]=1>C1COCC1>[O:4]=[C:2]1[NH:19][C:20]2=[N:21][CH:22]=[CH:23][C:24]([O:27][C:28]3[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:40])[C:36]([F:37])([F:38])[F:39])=[C:30]([F:41])[CH:29]=3)=[C:25]2[NH:26]1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 94429Triphosgene2×HCID 86616913HCID 86616913, compound

Product 1

HCID 57974630HCID 57974630, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Method E3 (with triphosgene and Pyridine). N-(4-(2,3-Diaminopyridin-4-yl-oxy)-2-fluorophenyl)-2,2,2-trifluoroacetamide (500 mg, 1.5 mmol) was dissolved in dry THF (20 mL), pyridine (1 mL) was added and the solution was cooled at 0° C. Triphosgene (445 mg, 1.5 mmol) in dry THF (10 mL) was added dropwise. The reaction mixture was stirred at room temperature for 48 hours. The solvent was evaporated and the residue washed with water. The precipitate was recovered by filtration to afford the title compound (260 mg, 49%). 1H-NMR (δ, ppm, DMSO-d6): 6.57 (d, 1H, HPy,5), 6.98 (d, 1H, Harom,Ph), 7.36 (d, 1H, Harom,Ph), 7.50 (d, 1H, Harom,Ph), 7.75 (d, 1H, HPy,6), 11.26 (s, 1H, NHPy3), 11.30 (s, 1H, NHCOCF3), 11.48 (s, 1H, NHPy2). LC-MS (m/z): 356 (M, 100).

Workup

  1. customThe solvent was evaporated
  2. washthe residue washed with water
  3. filtrationThe precipitate was recovered by filtration

Sources & evidence

ORD record
ord-4503aa50b270407b8a10a2ab2d3f47af
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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