Triethyl orthoacetate → 5-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline

HRID 432704노트

반응식

HRID 432704 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]3[N:24]=[N:25][N:26]=[C:16]3[C:15]=2[NH2:27])[CH:2]=1.[C:28](OCC)(OCC)(OCC)[CH3:29].C(Cl)(Cl)Cl.CO>ClCCCl>[CH3:28][C:29]1[N:13]([CH2:12][CH2:11][O:10][CH2:9][CH2:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]3[N:24]=[N:25][N:26]=[C:16]3[C:15]=2[N:27]=1

참가 물질

5

반응물 3

HCID 66221Triethyl orthoacetateHCID 18760199N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamineHCID 21584188Chloroform methanol

생성물 1

HCID 187601655-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline수율 98.1%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

Under an atmosphere of nitrogen, N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamine (0.70 g, 1.92 mmol) was dissolved in 1,2-dichloroethane (15 ml). Triethyl orthoacetate (0.53 ml, 2.88 mmol) was added via syringe and the reaction was heated to reflux for 3 hours. Analysis by thin layer chromatography (95/5 chloroform/methanol) showed complete consumption of the diamine. The reaction was quenched by the addition of water (15 ml). The phases were separated and the aqueous fraction was extracted with dichioromethane (3×10 ml). The combined organic fractions were washed with brine (15 ml), dried (Na2SO4), filtered and concentrated in vacuo to yield 0.73 g of 5-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline as a red oil. This material was used without further purification.

후처리

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. customconsumption of the diamine
  4. customThe reaction was quenched by the addition of water (15 ml)
  5. customThe phases were separated
  6. extractionthe aqueous fraction was extracted with dichioromethane (3×10 ml)
  7. washThe combined organic fractions were washed with brine (15 ml)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-afcc472c9197435ab6877ecff2e99128
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664260B2

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