Development of practical syntheses of potent non-nucleoside reverse transcriptase inhibitors

Tetrahedron

Volumn 65, Issue 26, 2009, Pages 5013-5023

  Kuethe, Jeffrey T ^a   Zhong, Yong Li ^a   Alam, Mahbub ^b   Alorati, Anthony D ^b   Beutner, Gregory L ^a   Cai, Dongwei ^a   Fleitz, Fred J ^a   Gibb, Andrew D ^b   Kassim, Amude ^a   Linn, Kathleen ^a   Mancheno, Danny ^a   Marcune, Benjamin ^a   Pye, Philip J ^a   Scott, Jeremy P ^b   Tellers, David M ^a   Xiang, Bangping ^a   Yasuda, Nobuyoshi ^a   Yin, Jingjun ^a   Davies, Ian W ^a,b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

(3 BENZYLOXYMETHYL 1H PYRAZOLO [3,4 B]PYRIDINE 6 YL)TERT BUTYLAMINE; 2 BENZYLOXY 1 (2,6 DIFLUORO PYRIDIN 3 YL)ETHANONE; 3 [5 (6 AMINO 1H PYRAZOLO [3,4 B]PYRIDINE 3 YLMETHOXY) 2 CHLORO PHENOXY] 5 CHLORO BENZONITRILE 4 TOLUENESULFONATE SALT; 3 [5 [6 TERT BUTYLAMINO 1] TETRAHYDRO PYRAN 2YL] 1H PYRAZOLO [3,4 B]PYRIDINE 3 YLMETHOXY] 2 CHLORO PHENOXY] 5 CHLORO BENZONITRILE; 3 [5 [6 TERT BUTYLAMINO 1H PYRAZOLO [3,4 B]PYRIDINE 3 YLMETHOXY] 2 CHLORO PHENOXY] 5 CHLORO BENZONITRILE BISULFATE; 3 BENZYLOXYMETHYL 1H PYRAZOLO [3,4 B]PYRIDINE 7 OXIDE; 3 BROMOMETHYLPYRAZOLO [3,4 B]PYRIDINE 1 CARBOXYLIC ACID TERT BUTYLESTER; 3 CHLORO 5 [2 CHLORO 5 (1H PYRAZOLO [3,4 B]PYRIDINE 3 YLMETHOXY)PHENOXY]BENZONITRILE; 3 CHLORO 5 [2 CHLORO 5 (7 OXY 1H PYRAZOLO [3,4 B]PYRIDINE 3 YLMETHOXY)PHENOXY]BENZONITRILE; 3 CHLORO 5 [2 CHLORO 5 [7 OXY 1 (TETRAHYDRO PYRAN 2YL) 1H PYRAZOLO[3,4 B]PYRIDINE 3 YLMETHOXY] PHENOXY]BENZONITRILE; [6 TERT BUTYLAMINO 1 (TETRAHYDRO PYRAN 2 YL) 1H PYRAZOLO [3,4 B]PYRIDINE 3 YL]METHANOL; [6 TERT BUTYLAMINO 1 (TETRAHYDRO PYRAN 2 YL) 1H PYRAZOLO [3,4 B]PYRIDINE 3 YL]METHYLENE BENZYLETHER; [6 TERT BUTYLAMINO 1 (TETRAHYDRO PYRANTETRAHYDROPYRAN 1H PYRAZOLO [3,4 B]PYRIDINE 3 YL]METHYLENE BENZYLETHER; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; GEL CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL;

EID: 65749120737     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.084     Document Type: Article

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21. In similar fashion as described for the preparation of compound 4, Scheme 1, the intermediate regioisomeric THP-protected pyrazole could be observed by HPLC. This intermediate converts to THP-pyrazole 22 upon heating.
22. Satisfactory elemental analysis could not be obtained for bromide 6 due to the instability of this intermediate.