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

HRID 627621ノート

反応式

HRID 627621 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2c495302748f4faeb821f46801f45028
出典データセット
uspto-grants-2016_04
特許番号
US09309263B2

反応ノート

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