Triethylamine → HCID 86723307, compound

HRID 2366206Notes

Reaction equation

HRID 2366206 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:12]=1[C:13](Cl)=[O:14].C(N(CC)CC)C>O1CCOCC1>[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:12]=1[C:13]([NH:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[F:8])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 601502892-Chloro-3-fluoropyridin-4-amine

Product 1

HCID 86723307HCID 86723307, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-3-fluoropyridin-4-ylamine (660 mg, 4.5 mmol), 2,6-dichlorobenzoyl chloride (1.43 mL, 2.10 g, 10.0 mmol) and triethylamine (1.53 mL, 1.11 g, 11.0 mmol) in dioxane (12 mL) was heated under reflux for 18 hours then cooled to ambient temperature. The resultant mixture was partitioned between EtOAc (50 mL) and water (50 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was triturated with diethyl ether, filtered, dried and further purified by silica gel flash chromatography (0-25% EtOAc in pentane) to afford the title compound as a pink solid (1.17 g, 81% yield). 1H NMR (300 MHz, CDCl3): δ 8.50 (t, J=5.3 Hz, 1H), 8.22 (d, J=5.5 Hz, 1H), 7.83 (br s, 1H), 7.40-7.39 (m, 3H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customThe resultant mixture was partitioned between EtOAc (50 mL) and water (50 mL)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diethyl ether
  9. filtrationfiltered
  10. customdried
  11. customfurther purified by silica gel flash chromatography (0-25% EtOAc in pentane)

Sources & evidence

ORD record
ord-6f63be0fb54f4f77b46e6ff03437ed9b
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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