HCID 66648850, compound → HCID 66648890, compound

HRID 419118Notes

Reaction equation

HRID 419118 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[C:16]([C:22]([C:24]3[CH:25]([CH3:32])[N:26]([OH:31])[CH:27]=[CH:28][C:29]=3[CH3:30])=[O:23])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)COC)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34]>Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:15]2[C:16]([C:22]([C:24]3[CH:25]([CH3:32])[N:26]([OH:31])[CH:27]=[CH:28][C:29]=3[CH3:30])=[O:23])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:33]([F:36])([F:34])[F:35]

Participants

4

Reactant 1

HCID 66648850HCID 66648850, compound

Product 1

HCID 66648890HCID 66648890, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 4-Chloro-N-[5-chloro-2-(1-hydroxy-2,4-dimethyl-pyridine-3-carbonyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (21 mg) in 6 ml of HCl (4M in dioxane) and 2 mL of water was refluxed for 2 hours. After cooling to rt the mixture was concentrated and was added 3 mL of water. Sodium bicarbonate was added until the final pH was 6. The mixture was extracted with ethyl acetate, dried and concentrated. The residue was further purified via short flash column (8% methanol in DCM) to afford 7.9 mg of title compound as an off white solid. MS: (M+H)/z=520.0.

Workup

  1. concentrationwas concentrated
  2. additionwas added 3 mL of water
  3. additionSodium bicarbonate was added until the final pH was 6
  4. extractionThe mixture was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was further purified via short flash column (8% methanol in DCM)

Sources & evidence

ORD record
ord-ceaac7c73250421389708f1bbfc606e5
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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