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Volumn 12, Issue 15, 2010, Pages 3422-3425

Target-directed synthesis of antibacterial drug candidate GSK966587

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; GSK966587; NAPHTHYRIDINE DERIVATIVE;

EID: 77955142296     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101235f     Document Type: Article
Times cited : (32)

References (36)
  • 3
    • 77955143226 scopus 로고    scopus 로고
    • For related quinoline metalation strategies, see
    • For related quinoline metalation strategies, see
  • 8
    • 77955141423 scopus 로고    scopus 로고
    • 2-Chloro-5-fluoro-3-pyridinamine: $2295/kg from Archimica
    • 2-Chloro-5-fluoro-3-pyridinamine: $2295/kg from Archimica.
  • 9
    • 77955158445 scopus 로고    scopus 로고
    • For a similar strategy to a [1.5]naphthyridinone, see
    • For a similar strategy to a [1.5]naphthyridinone, see
  • 12
    • 85027892580 scopus 로고    scopus 로고
    • references cited therein
    • Littke, A. F.; Fu, G. C. Org. Synth. 2005, 81, 63 and references cited therein
    • (2005) Org. Synth. , vol.81 , pp. 63
    • Littke, A.F.1    Fu, G.C.2
  • 16
    • 77955146253 scopus 로고    scopus 로고
    • A similar path to a [1,8]naphthyridinone has been reported in 42% yield
    • A similar path to a [1,8]naphthyridinone has been reported in 42% yield
  • 18
    • 77955136757 scopus 로고    scopus 로고
    • 2NMe and xylene at 135 °C, the reaction from isolated 9 to napthyridinone 7 was very slow, suggesting that Pd catalyst is needed for the conversion
    • 2NMe and xylene at 135 °C, the reaction from isolated 9 to napthyridinone 7 was very slow, suggesting that Pd catalyst is needed for the conversion.
  • 19
    • 77955143225 scopus 로고    scopus 로고
    • 2 reaction in order to alleviate safety concerns around the potential formation of dimethylcarbamoyl chloride (DMCC), a known potent carcinogen. See
    • 2 reaction in order to alleviate safety concerns around the potential formation of dimethylcarbamoyl chloride (DMCC), a known potent carcinogen. See
  • 21
    • 77955168606 scopus 로고    scopus 로고
    • The mono-HCl salt of 10 did not react with MeOH; however, even a catalytic amount of HCl could convert the mono-HCl salt to 11. Thanks to Huan Wang (GSK) for this suggestion
    • The mono-HCl salt of 10 did not react with MeOH; however, even a catalytic amount of HCl could convert the mono-HCl salt to 11. Thanks to Huan Wang (GSK) for this suggestion.
  • 22
    • 77955160175 scopus 로고    scopus 로고
    • For a review, see
    • For a review, see
  • 24
    • 77955168535 scopus 로고    scopus 로고
    • This regiochemical discrepancy has been observed in deprotonation of pyridines
    • This regiochemical discrepancy has been observed in deprotonation of pyridines
  • 25
    • 0035824331 scopus 로고    scopus 로고
    • The regiochemistry of the undesired mono-iodide has not been confirmed
    • Imahori, T.; Uchiyama, M.; Sakamoto, T.; Kondo, Y. Chem. Commun. 2001, 2450 The regiochemistry of the undesired mono-iodide has not been confirmed.
    • (2001) Chem. Commun. , pp. 2450
    • Imahori, T.1    Uchiyama, M.2    Sakamoto, T.3    Kondo, Y.4
  • 26
    • 77955155998 scopus 로고    scopus 로고
    • 2Li is known to react with haloarenes to form benzynes
    • 2Li is known to react with haloarenes to form benzynes
  • 28
    • 77955149809 scopus 로고    scopus 로고
    • A report of the unsuccessful use of this reagent in a screen of various zincate bases has appeared
    • A report of the unsuccessful use of this reagent in a screen of various zincate bases has appeared
  • 33
    • 77955148690 scopus 로고    scopus 로고
    • A 65-70% yield was obtained via EtOAc/cyclohexane crystallization; however, this procedure remains in need of optimization
    • A 65-70% yield was obtained via EtOAc/cyclohexane crystallization; however, this procedure remains in need of optimization.
  • 34
    • 77955123896 scopus 로고    scopus 로고
    • Chloromethane is generated in the conversion of 17 to 18 and safety precautions (proper ventilation) were taken
    • Chloromethane is generated in the conversion of 17 to 18 and safety precautions (proper ventilation) were taken.
  • 35
    • 77955124140 scopus 로고    scopus 로고
    • With the opposite enantiomers of 16, 17, and 18, an overall yield of 71% was obtained when epoxy alcohol 17 was isolated
    • With the opposite enantiomers of 16, 17, and 18, an overall yield of 71% was obtained when epoxy alcohol 17 was isolated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.