Cyanuric chloride → HCID 89689825, compound

HRID 595471Notes

Reaction equation

HRID 595471 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][CH:12]([CH3:14])[CH3:13])[C:5]([C:6]([NH2:8])=O)=[CH:4][N:3]=1.N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][CH:12]([CH3:14])[CH3:13])[C:5]([C:6]#[N:8])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 89689729HCID 89689729, compound

Product 1

HCID 89689825HCID 89689825, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-chloro-4-(isopropylamino)nicotinamide (17) (2.5 g, 11.7 mmol) in DMF (10 mL), cyanuric chloride (11.7 mmol, 1 equiv.) was added at 0° C. and stirred for 2 h. The reaction mixture was quenched with ice-cool water and extracted twice using EtOAc. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography, silica gel (60-120 mesh) and EtOAc:pet Ether as eluent to furnish 6-chloro-4-(isopropylamino)nicotinonitrile. 1H NMR: 400 MHz, CDCl3: δ 1.32 (d, J=6.40 Hz, 6H), 3.69-3.79 (m, 1H), 4.91 (bs, 1H), 6.57 (s, 1H), 8.23 (s, 1H).

Workup

  1. customThe reaction mixture was quenched with ice-
  2. temperaturecool water
  3. extractionextracted twice using EtOAc
  4. customThe organic layer was collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by column chromatography, silica gel (60-120 mesh) and EtOAc

Sources & evidence

ORD record
ord-36c821a60a444519bd18e23c76aae055
Source dataset
uspto-grants-2016_01
Patent number
US09242976B2

Reaction notes

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