Hydrochloric Acid → HCID 58990836, compound

HRID 1020218Notes

Reaction equation

HRID 1020218 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH:19][S:20]([C:23]2([CH2:26][CH:27]=[O:28])[CH2:25][CH2:24]2)(=[O:22])=[O:21])=[CH:12][N:13]([CH3:18])[C:14](=[O:17])[C:15]=1[CH3:16].[OH:29]P([O-])(O)=O.[K+].CC(=CC)C.Cl([O-])=O.[Na+].Cl>C(O)(C)(C)C.O>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH:19][S:20]([C:23]2([CH2:26][C:27]([OH:29])=[O:28])[CH2:24][CH2:25]2)(=[O:22])=[O:21])=[CH:12][N:13]([CH3:18])[C:14](=[O:17])[C:15]=1[CH3:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 57458190HCID 57458190, compound

Product 1

HCID 58990836HCID 58990836, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

To a dark brown solution of N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1-(2-oxoethyl)cyclopropane-1-sulfonamide, potassium phosphate monobasic (27 mg, 0.20 mmol), and 2-methyl-2-butene (0.45 mL, 0.90 mmol) in tert-butanol (4 mL) and H2O (1 mL) at 0° C. is added sodium chlorite (55 mg, 0.60 mmol). After stirring at 0° C. for 30 min, the reaction is warmed to room temperature and stirred for 16 h. To the reaction is added aqueous HCl solution (5 mL, 1N) and saturated aqueous NaS2O3 solution (5 mL). The mixture is extracted with CH2Cl2 (20 mL), dried over MgSO4, concentrated, and may be purified by silica gel chromatography (CH2Cl2:CH3OH=90:10).

Workup

  1. temperaturethe reaction is warmed to room temperature
  2. stirringstirred for 16 h
  3. extractionThe mixture is extracted with CH2Cl2 (20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custommay be purified by silica gel chromatography (CH2Cl2:CH3OH=90:10)

Sources & evidence

ORD record
ord-5187c6001f444851bf63cbc8cf53dacc
Source dataset
uspto-grants-2014_05
Patent number
US08716318B2

Reaction notes

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