1,4-Dioxane → 2-Amino-5-pyridin-3-ylthiophene-3-carbonitrile

HRID 386134Notes

Reaction equation

HRID 386134 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][C:12]=1[C:13]#[N:14])(C)(C)C.O1CCOCC1>Cl>[NH2:7][C:8]1[S:9][C:10]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][C:12]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 70842621HCID 70842621, compound

Product 1

HCID 686716452-Amino-5-pyridin-3-ylthiophene-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl(3-cyano-5-pyridin-3-yl-2-thienyl)carbamate (800 mg, 2.07 mmol) was dissolved in 4M hydrochloric acid in dioxane (10.4 ml, 41.6 mmol) and the mixture was stirred at room temperature for 6 h. The mixture was quenched with 1N sodium hydroxide (50 mL) and extracted with ethyl acetate (3×100 mL). The combined organics were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound as a solid.

Workup

  1. customThe mixture was quenched with 1N sodium hydroxide (50 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90de99c0f10a42e5893ee2e2ccc47b85
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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