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

HRID 627621

반응식

HRID 627621 반응식
[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

참가 물질

5

반응물 3

HCID 313Hydrochloric Acid2회HCID 643216Thiophene-3,4-diamineHCID 23682802CID 23682802

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2c495302748f4faeb821f46801f45028
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309263B2

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