Hydrochloric Acid → HCID 71144053, compound

HRID 2370811Notes

Reaction equation

HRID 2370811 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][N:17]=2)[NH:9]S(C(C)(C)C)=O)=[CH:4][CH:3]=1.Cl>CO>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:16]2[C:21]([C:22]([F:25])([F:23])[F:24])=[CH:20][CH:19]=[CH:18][N:17]=2)[NH2:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71143997HCID 71143997, compound

Product 1

HCID 71144053HCID 71144053, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-((4-iodophenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide in MeOH (5 mL) was added HCl (2.0 mL, 8.0 mmol) (4.0 M in 1,4-dioxane). The reaction was stirred at rt under N2 for 18 h. The reaction was then concentrated, and the residue was purified by reverse-phase preparative HPLC (Shimadzu) on a Phenomenex Gemini™ column (5 micron, C18, 110 Å, Axia, 100×30 mm) eluting at 45 mL/min with a linear gradient of 10% to 100% MeCN (0.1% TFA) in H2O (0.1% TFA) over 20 minutes. The product-containing fractions were combined, concentrated, dissolved in DCM (5 mL) and extracted with saturated aqueous NaHCO3 (2×5 mL). The organic layer was dried and concentrated to give (4-iodophenyl)(3-(trifluoromethyl)-pyridin-2-yl)methanamine as a clear oil.

Workup

  1. concentrationThe reaction was then concentrated
  2. customthe residue was purified by reverse-phase preparative HPLC (Shimadzu) on a Phenomenex Gemini™ column (5 micron, C18, 110 Å, Axia, 100×30 mm)
  3. washeluting at 45 mL/min with a linear gradient of 10% to 100% MeCN (0.1% TFA) in H2O (0.1% TFA) over 20 minutes
  4. concentrationconcentrated
  5. dissolutiondissolved in DCM (5 mL)
  6. extractionextracted with saturated aqueous NaHCO3 (2×5 mL)
  7. customThe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3e41340855304570ad7798c406c5ab0c
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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