Hydrochloric Acid → HCID 46916396, compound

HRID 1186767Notes

Reaction equation

HRID 1186767 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:17]1[N:18]([CH3:35])[C:19](=[O:34])[C:20]([CH3:33])=[CH:21][C:22]=1[NH:23][S:24]([C:27]1([CH2:30][CH2:31][OH:32])[CH2:29][CH2:28]1)(=[O:26])=[O:25])C(=O)OC(C)(C)C.Cl.O1CCOCC1>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:17]1[N:18]([CH3:35])[C:19](=[O:34])[C:20]([CH3:33])=[CH:21][C:22]=1[NH:23][S:24]([C:27]1([CH2:30][CH2:31][OH:32])[CH2:29][CH2:28]1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 66701633HCID 66701633, compound

Product 1

HCID 46916396HCID 46916396, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (2-fluoro-4-iodophenyl)[3-({[1-(2-hydroxyethyl)cyclopropyl]sulfonyl}amino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-2-yl]carbamate (324 mg, 0.521 mmol) in dry THF under a nitrogen atmosphere was added a solution of HCl in dioxane (30 eq, 3.80 ml, 15.640 mmol). The mixture was stirred at room temperature for 18 hours, after which again a solution of HCl in dioxane (8 eq, 1.01 ml, 4.055 mmol) was added and stirred for another 18 hours. The mixture was partitioned between ethyl acetate and aq. NaOH (2 N) and the aqueouse layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated in vacuo. The crude material was purified by flash chromatography to afford the title compound (172 mg, 65%).

Workup

  1. stirringstirred for another 18 hours
  2. customThe mixture was partitioned between ethyl acetate and aq. NaOH (2 N)
  3. extractionthe aqueouse layer was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-9eea9f8c99464fe0bee8bac132690d90
Source dataset
uspto-grants-2014_03
Patent number
US08673919B2

Reaction notes

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