Hydrochloric Acid → 3-Aminothieno[3,2-b]pyridine-6-carbonitrile

HRID 627621Notes

Reaction equation

HRID 627621 reaction equation
[C:1](/[C:3](/[CH:6](OC)OC)=[CH:4]\[O-])#[N:2].[Na+].Cl.[S:13]1[CH:17]=[C:16]([NH2:18])[C:15]([NH2:19])=[CH:14]1>CO>[NH2:19][C:15]1[C:16]2=[N:18][CH:4]=[C:3]([C:1]#[N:2])[CH:6]=[C:17]2[S:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 643216Thiophene-3,4-diamineHCID 23682802CID 23682802

Product 1

HCID 139394733-Aminothieno[3,2-b]pyridine-6-carbonitrileYield 23.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of sodium (E)-2-cyano-3,3-dimethoxyprop-1-en-1-olate (1012 mg, 6.13 mmol) in methanol (12 mL) was added concentrated hydrochloric acid (503 μL 6.13 mmol). The solution was stirred for 5 minutes, and then a solution of thiophene-3,4-diamine (700 mg, 6.13 mmol) in methanol (12 mL) was added. The solution was stirred at reflux for 3 hours, and then a solution of concentrated HCl (1.0 mL) in methanol (2 mL) was added. The reaction was stirred at reflux for an additional two hours, quenched with TEA (3 mL), and concentrated. The crude product was purified via silica gel chromatography, eluting with 0-100% ethyl acetate in heptanes, to provide the title compound (250 mg, 1.427 mmol). MS m/z=176 (M+H).

Workup

  1. stirringThe solution was stirred
  2. temperatureat reflux for 3 hours
  3. stirringThe reaction was stirred
  4. temperatureat reflux for an additional two hours
  5. customquenched with TEA (3 mL)
  6. concentrationconcentrated
  7. customThe crude product was purified via silica gel chromatography
  8. washeluting with 0-100% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-2c495302748f4faeb821f46801f45028
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

Loading…