HCID 50912932, compound → Refametinib

HRID 1895528Notes

Reaction equation

HRID 1895528 reaction equation
[F:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])=[C:4]([NH:11][S:12]([C:15]2([CH2:18][C@H:19]3[CH2:23][O:22]C(C)(C)[O:20]3)[CH2:17][CH2:16]2)(=[O:14])=[O:13])[C:5]([O:9][CH3:10])=[CH:6][C:7]=1[F:8]>C1COCC1.Cl>[F:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])=[C:4]([NH:11][S:12]([C:15]2([CH2:18][C@H:19]([OH:20])[CH2:23][OH:22])[CH2:17][CH2:16]2)(=[O:13])=[O:14])[C:5]([O:9][CH3:10])=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 50912932HCID 50912932, compound

Product 1

HCID 44182295Refametinib

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)—N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)cyclopropane-1-sulfonamide is dissolved in a mixture of THF and HCl and stirred overnight at room temperature. The solvents are removed under reduced pressure and the residue dissolved in ethyl acetate. The organic phase is washed with aqueous NaHCO3, dried (Na2SO4), and concentrated.

Workup

  1. customThe solvents are removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic phase is washed with aqueous NaHCO3
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e542915eb496487ca0ddc7ca975f4a13
Source dataset
uspto-grants-2013_08
Patent number
US08513443B2

Reaction notes

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