Hydrochloric Acid → HCID 57425774, compound

HRID 1360126Notes

Reaction equation

HRID 1360126 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([NH:23]S(C(C)(C)C)=O)[CH:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.C([O-])(O)=O.[Na+]>CO.O>[NH2:23][CH:9]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])[CH:10]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66962784HCID 66962784, compound

Product 1

HCID 57425774HCID 57425774, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

N-[1-(3-cyanophenyl)-2,2-dipyridin-3-ylethyl]-2-methylpropane-2-sulfinamide (Diastereomer B, 1.567 g, 3.87 mmol) was dissolved in CH3OH (15 mL) and the solution was cooled to 0° C. HCl (4 M solution in dioxane, 2.905 mL, 11.62 mmol) was added drop-wise. The reaction was allowed to warm to RT and was stirred for 7 hr. The reaction was diluted with H2O and the pH was adjusted to pH=7 using saturated aqueous NaHCO3. The product was extracted with ethyl acetate (3×75 mL) followed by isobutanol (6×50 mL). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to afford 3-(1-amino-2,2-dipyridin-3-ylethyl)benzonitrile as a foamy light yellow solid.

Workup

  1. temperatureto warm to RT
  2. extractionThe product was extracted with ethyl acetate (3×75 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0ac7bcceb86480fba8029a84ffded89
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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