1-Ethyl-3-(5-hydroxymethyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea → 1-Ethyl-3-(5-formyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea

HRID 2112943ノート

反応式

HRID 2112943 の反応式
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:23]=[C:10]2[CH:11]=[C:12]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:13]=[C:14]([CH2:15][OH:16])[N:9]2[N:8]=1)=[O:5])[CH3:2]>C1COCC1.O=[Mn]=O>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:23]=[C:10]2[CH:11]=[C:12]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:13]=[C:14]([CH:15]=[O:16])[N:9]2[N:8]=1)=[O:5])[CH3:2]

参加物

4

反応物 1

HCID 688348081-Ethyl-3-(5-hydroxymethyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea

生成物 1

HCID 866180221-Ethyl-3-(5-formyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

The product of Step 1 (154 mg, 0.50 mmol) was dissolved in THF (50 mL), to which was added MnO2 (250 mg). This mixture was heated at reflux for 18 h., at which point two further portions (50 mg each) were added over the next 8 hours. Finally, the mixture was heated at reflux for 18 h., allowed to cool, then the MnO2 removed by filtration over celite which was washed with THF and MeOH/CH2Cl2. The solvent was removed under reduced pressure to afford 1-ethyl-3-(5-formyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea as a crude solid. LCMS (APCI+) 311.

後処理

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 18 h., at which point two further portions (50 mg each)
  3. additionwere added over the next 8 hours
  4. temperatureFinally, the mixture was heated
  5. temperatureat reflux for 18 h.
  6. temperatureto cool
  7. customthe MnO2 removed by filtration over celite which
  8. washwas washed with THF and MeOH/CH2Cl2
  9. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-8b21061d454c4793b89cf04555bcf3b2
出典データセット
uspto-grants-2009_04
特許番号
US07524860B2

反応ノート

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