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 2112943노트

반응식

HRID 2112943 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8b21061d454c4793b89cf04555bcf3b2
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524860B2

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