Sodium Hydroxide → HCID 86723312, compound

HRID 2366226Notes

Reaction equation

HRID 2366226 reaction equation
[Cl:1][C:2]1[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[C:27]([F:33])[C:3]=1[C:4]([N:6](C(=O)C1C(F)=CC(C#N)=CC=1Cl)[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[C:8]=1[F:14])=[O:5].[OH-].[Na+]>CO.O1CCOCC1>[Cl:1][C:2]1[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[C:27]([F:33])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[C:8]=1[F:14])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 867233112-Chloro-N-(2-chloro-4-cyano-6-fluoro-benzoyl)-N-(2-chloro-3-fluoropyridin-4-yl)-4-cyano-6-fluorobenzamide

Product 1

HCID 86723312HCID 86723312, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-chloro-N-(2-chloro-4-cyano-6-fluorobenzoyl)-N-(2-chloro-3-fluoro-pyridin-4-yl)-4-cyano-6-fluoro-benzamide (0.865 g, 1.7 mmol) in MeOH (8.5 mL) and dioxane (8.5 mL) was added sodium hydroxide (0.102 g, 2.5 mmol). The resulting mixture stirred at room temperature for 2.5 hours and then concentrated under reduced pressure. The residue was partitioned between DCM and saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0-100% DCM in pentane to give the desired compound as an off-white solid (0.308 g, 55% yield). 1H NMR (300 MHz, CDCl3): δ 8.49-8.40 (m, 1H), 8.25 (d, J=5.4 Hz, 1H), 7.98 (br s, 1H), 7.64 (t, J=1.3 Hz, 1H), 7.47 (dd, J=7.9, 1.5 Hz, 1H). LCMS (Method D): RT=3.33 min, m/z: 328 [M+H+].

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between DCM and saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluting with 0-100% DCM in pentane

Sources & evidence

ORD record
ord-4ca4bfb729a44bbf81a6fdcfc430e491
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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