Triethylamine → HCID 86650611, compound

HRID 1963880Notes

Reaction equation

HRID 1963880 reaction equation
Cl[C:2]1[N:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:11][C:12]1[CH:17]=C[C:15](CN)=[CH:14][CH:13]=1.C([N:22]([CH2:25][CH3:26])CC)C>CN1C(=O)CCC1.O>[Cl:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([NH:22][CH2:25][C:26]2[CH:15]=[CH:14][CH:13]=[C:12]([F:11])[CH:17]=2)[N:9]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 126055382,6-Dichloropyridine-3-carbonitrile

Product 1

HCID 86650611HCID 86650611, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

2,6-dichloronicotinonitrile (0.500 g, 2.89 mmol), (4-fluorophenyl)methanamine (0.816 mL, 0.904 g, 7.23 mmol), and triethylamine (1.21 mL, 0.877 g, 8.67 mmol) were all mixed in NMP (10 mL). The resulting solution then was heated at 50° C. for 18 hr. The reaction mixture was then poured in H2O (25 mL), and extracted with EtOAc (3×25 mL). The combined extracts were washed with H20 (4×25 mL), and brine (1×25 mL). The organic layer was separated and dried (Na2SO4), filtered, and the solvent removed in vacuo. The resulting residue was purified using silica gel column chromatography. Elution using 1 EtOAc/3 hexanes to 3 EtOAc/1 hexanes afforded 0.6024 g (80%) of 6-chloro-2-(3-fluorobenzylamino)nicotinonitrile. LCMS (m/z): 350.0 (MH+), retention time=0.96 min. 1H NMR (300 MHz, CDCl3) δ 4.58 (d, J=5.86 Hz, 2 H) 5.48 (br. s., 1 H) 6.30 (d, J=8.50 Hz, 1 H) 6.96-7.06 (m, 2 H) 7.10 (d, J=7.62 Hz, 1 H) 7.28-7.38 (m, 1 H) 7.58 (d, J=8.79 Hz, 1 H).

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe combined extracts were washed with H20 (4×25 mL), and brine (1×25 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe resulting residue was purified
  8. washElution

Sources & evidence

ORD record
ord-a8933765d6c74880bff40f4f91f709d5
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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