Hydrochloric Acid → HCID 66759887, compound

HRID 389422Notes

Reaction equation

HRID 389422 reaction equation
[Cl:1][C:2]1[O:25][C:5]2=[C:6]([N:10](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.Cl.O1CCOCC1>C(Cl)Cl>[Cl:1][C:2]1[O:25][C:5]2=[C:6]([NH2:10])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66760259HCID 66760259, compound

Product 1

HCID 66759887HCID 66759887, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

Di-tert-butyl (2-chlorofuro[2,3-c]pyridin-7-yl)imidodicarbonate (18.0 g, 49.1 mmol) in DCM (100 mL) was cooled in an ice bath and treated with 4 N HCl in 1,4-dioxane (75 mL, 300 mmol) added slowly over several minutes. The reaction was removed from the cooling bath and heated at 55° C. for 16 h. The mixture was concentrated in vacuo. The residue was suspended in DCM and treated with saturated NaHCO3 until the pH reached ˜8.5. The organic layer was washed with water and brine and then dried over anhydrous Na2SO4. The material was purified by flash chromatography (50% EtOAc:DCM) to provide 8.2 g (100%) of the title compound as a white solid. 1H NMR (CDCl3, 400 MHz): δ 4.75 (br s, 2H), 6.54 (s, 1H), 6.85 (d, J=5.3 Hz, 1H), 7.86 (d, J=5.3 Hz, 1H); MS (ESI): 169.12 [M+H]+.

Workup

  1. additionadded slowly over several minutes
  2. customThe reaction was removed from the cooling bath
  3. concentrationThe mixture was concentrated in vacuo
  4. additiontreated with saturated NaHCO3 until the pH
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe material was purified by flash chromatography (50% EtOAc:DCM)

Sources & evidence

ORD record
ord-0f51e26dad2e4324815a4bbd09f4cc7d
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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