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Volumn 6, Issue 24, 1996, Pages 3029-3034

SAR of 2-benzyl-4-aminopiperidines NK1 antagonists. Part 2. Synthesis of CGP 49823

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZYL 1 (3,5 DIMETHYLBENZOYL) 4 (4 QUINOLINYLMETHYLAMINO)PIPERIDINE; NEUROKININ 1 RECEPTOR; NEUROKININ 1 RECEPTOR ANTAGONIST; PIPERIDINE DERIVATIVE; SUBSTANCE P; UNCLASSIFIED DRUG;

EID: 0030591843     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00563-X     Document Type: Article
Times cited : (16)

References (31)
  • 13
    • 0011348385 scopus 로고    scopus 로고
    • note
    • 3CN gave good yields, but a lower trans/cis ratio; other acids gave unsatisfactory results.
  • 14
    • 0011348386 scopus 로고    scopus 로고
    • note
    • 3CN) 7.32 - 7.26 (m, 2H), 7.23 - 7.18 (m, 3H), 6.26 - 6.15 (br, 1H), 3.60 (ttd, J=3.8, 11.6 and 7.7 Hz, 1H), 2.96 ( ddd, J= 2.5, 4.2 and 12.0 Hz, 1H), 2.76 - 2.68 (m, 1H), 2.66 - 2.58 (m, 2H), 2.52 (dt, J=2.5 and 12.0 Hz, 1H), 1.80 -1.69 (m, 2H), 1.43 -1.28 (br, 1H), 1.17 (dt, J=4.2 and 12.0 Hz, 1H), 0.90 (q, J=11.6 Hz, 1H).
  • 15
    • 0011309549 scopus 로고    scopus 로고
    • note
    • 10. A concomitantly occurring 2-aza-Cope rearrangement 5a→5c ,which then cyclizes to racemic 6, would explain this result: (equation presented) See for instance: (a) Ref. 11;
  • 18
    • 0011316307 scopus 로고    scopus 로고
    • note
    • ®) of its benzyloxycarbonyl derivative 6.
  • 19
    • 0026644849 scopus 로고
    • (11) To our best knowledge this procedure is the first example of a selective acylation of a secondary amine in presence of a primary amine using an acid chloride as acylating agent. Selective Boc-protection of a secondary amine in presence of a primary amine has been reported: Prugh, J.D.; Birchenough, L.A.; Egbertson, M.S. Synth. Commun. 1992, 22, 2357.
    • (1992) Synth. Commun. , vol.22 , pp. 2357
    • Prugh, J.D.1    Birchenough, L.A.2    Egbertson, M.S.3
  • 20
    • 0001673091 scopus 로고
    • Schreiber, S.L., Ed.; Pergamon Press; Oxford
    • (12) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2, pp. 1047-1082, Schreiber, S.L., Ed.; Pergamon Press; Oxford, 1991.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 27
    • 0011308647 scopus 로고    scopus 로고
    • note
    • (17) A side reaction was the simultaneous cleavage of the benzamide.
  • 28
  • 31
    • 0011353794 scopus 로고    scopus 로고
    • unpublished results
    • (21) Veenstra, S.J. unpublished results.
    • Veenstra, S.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.