Hydrochloric Acid → HCID 90413867, compound

HRID 57443Notes

Reaction equation

HRID 57443 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C@H:13]([NH:15][S@@](C(C)(C)C)=O)[CH3:14])=[N:9]2)=[CH:4][CH:3]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C@H:13]([NH2:15])[CH3:14])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90415586(R)-N-((R)-1-(1-(4-chlorophenyl)-1H-pyrazol-3-yl)ethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 90413867HCID 90413867, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)—N—((R)-1-(1-(4-chlorophenyl)-1H-pyrazol-3-yl)ethyl)-2-methylpropane-2-sulfinamide (0.98 g, 3.01 mmol) in dioxane (10 ml) was added dropwise HCl (1.504 ml, 6.01 mmol). The reaction was stirred at room temperature for 30 minutes. LCMS indicated complete conversion to product. The reaction mixture was concentrated and DCM (20 mL) and saturated NaHCO3 solution (10 mL) was added to the residue. The mixture was stirred for 10 minutes and phases were separated. Aqueous layer was then extracted with DCM (2×10 mL), and the combined organic was dried (Na2SO4) and concentrated to give product (0.556 g). LCMS (B) m/z 222.2 (M+H)+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionDCM (20 mL) and saturated NaHCO3 solution (10 mL) was added to the residue
  3. stirringThe mixture was stirred for 10 minutes
  4. customphases were separated
  5. extractionAqueous layer was then extracted with DCM (2×10 mL)
  6. dry with materialthe combined organic was dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fbe6f3c8987446e6bf8dd9e5b09fc317
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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