Hydrochloric Acid → 1-(2-Hydroxyethyl)-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide

HRID 598416Notes

Reaction equation

HRID 598416 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][C:9]1([S:12]([NH:15][C:16]2[C:21]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=3[F:30])=[C:20]([CH3:31])[C:19](=[O:32])[N:18]([CH3:33])[CH:17]=2)(=[O:14])=[O:13])[CH2:11][CH2:10]1)(C)(C)C.Cl>C1COCC1>[OH:6][CH2:7][CH2:8][C:9]1([S:12]([NH:15][C:16]2[C:21]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=3[F:30])=[C:20]([CH3:31])[C:19](=[O:32])[N:18]([CH3:33])[CH:17]=2)(=[O:14])=[O:13])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 589908271-[2-(tertbutyldimethylsilanyloxy)ethyl]-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide

Product 1

HCID 589908331-(2-Hydroxyethyl)-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(tertbutyldimethylsilanyloxy)ethyl]-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide (20 mg, 0.032 mmol) in THF (2 mL) at 0° C. is added 1N HCl (0.128 mL. 0.128 mmol). The ice-bath is removed after 30 minutes and the solution stirred at room temperature for 45 minutes. Then the solution is cooled to 0° C., saturated NaHCO3 (3 mL) solution is added, and extracted with ethyl acetate (3×5 mL). The combined organic layers are concentrated under reduced pressure to give the title compound.

Workup

  1. customThe ice-bath is removed after 30 minutes
  2. temperatureThen the solution is cooled to 0° C.
  3. additionsaturated NaHCO3 (3 mL) solution is added
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. concentrationThe combined organic layers are concentrated under reduced pressure

Sources & evidence

ORD record
ord-ec136dfcb55e4bbaad1014a11e404fb1
Source dataset
uspto-grants-2011_03
Patent number
US07897624B2

Reaction notes

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