Hydrochloric Acid → HCID 86723308, compound

HRID 2366209Notes

Reaction equation

HRID 2366209 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Cl:12][C:13]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([Cl:24])[C:14]=1[C:15](Cl)=[O:16].Cl>CN(C=O)C.C(Cl)Cl.O>[Cl:12][C:13]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([Cl:24])[C:14]=1[C:15]([NH:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[F:8])=[O:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 601502892-Chloro-3-fluoropyridin-4-amineHCID 866489562,6-Dichloro-4-cyanobenzoyl chloride

Product 1

HCID 86723308HCID 86723308, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-3-fluoropyridin-4-ylamine (146 mg, 10 mmol) was added to a suspension of sodium hydride (60% dispersed in mineral oil, 80 mg, 2.0 mmol) in DMF (5 mL). The mixture was stirred for 30 minutes then 2,6-dichloro-4-cyano-benzoyl chloride (250 mg, 1.1 mmol) was added and stirring continued for 18 hours. Water (10 mL) and DCM (20 mL) were added to the reaction, and the resultant mixture was acidified with 1M HCl. The organic phase was separated, washed with brine (10 mL), dried over MgSO4, and concentrated to dryness under reduced pressure. The residue was purified by silica gel flash chromatography eluting with DCM. The crude product was triturated with diethyl ether to give the desired compound as a white solid (230 mg, 67% yield). 1H NMR (400 MHz, CDCl3): δ 8.46 (t, J=5.3 Hz, 1H), 8.25 (d, J=5.5 Hz, 1H), 7.88 (br s, 1H), 7.72 (s, 2H).

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. customThe organic phase was separated
  4. washwashed with brine (10 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography
  8. washeluting with DCM
  9. customThe crude product was triturated with diethyl ether

Sources & evidence

ORD record
ord-ec9bf64c5c4946de980881265aec6ee8
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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