Synthesis of 2-bromo-7-methyl-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one and 3-alkyl-2-bromo-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one and their selective elaboration

被引:5
作者
Eckhardt, Matthias [1 ]
Hauel, Norbert [1 ]
Langkopf, Elke [1 ]
Himmelsbach, Frank [1 ]
机构
[1] Boehringer Ingelheim Pharma GmbH & Co KG, Dept Chem Res, D-88400 Biberach, Germany
关键词
imidazoles; imidazopyridazinones; regiocontrol; combinatorial chemistry;
D O I
10.1016/j.tetlet.2008.01.102
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two synthetic routes to the versatile 3,5-dihydro-imidazo[4,5-d]pyridazin-4-ones 2 and 5 have been developed that allow the production of multigram quantities without the need of any chromatographic purification. Broad and selective elaboration of the heteroaromatic scaffolds has also been accomplished. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1931 / 1934
页数:4
相关论文
共 13 条
[1]   METALATION AND REACTION OF 4,5-DICYANOIMIDAZOLES WITH ALKYLLITHIUM REAGENTS [J].
APEN, PG ;
RASMUSSEN, PG .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (05) :1091-1095
[2]   HETEROCYCLIC HYDRAZONES AND HYDRAZINES .4. SYNTHESIS OF HYDRAZINE DERIVATIVES IN THE SERIES OF [4,5-D] IMIDAZO-4-PYRIDAZINONES [J].
BELJEANLEYMARIE, M ;
PAYS, M ;
RICHER, JC .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (11) :2563-2566
[3]  
BOEHRINGER INGELHEIM, 2004, Patent No. 2004111051
[5]  
ECKHARDT M, 2005, Patent No. 2005110999
[6]   8-(3-(R)-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydropurine-2,6-dione (BI 1356), a highly potent, selective, long-acting, and orally bioavailable DPP-4 inhibitor for the treatment of type 2 diabetes [J].
Eckhardt, Matthias ;
Langkop, Elke ;
Mark, Michael ;
Tadayyon, Mob ;
Thomas, Leo ;
Nar, Herbert ;
Pfrengle, Waldemar ;
Guth, Brian ;
Lotz, Ralf ;
Sieger, Peter ;
Fuchs, Holger ;
Himmelsbach, Frank .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (26) :6450-6453
[7]   MULTIFUNCTIONALIZATION OF IMIDAZOLE VIA SEQUENTIAL HALOGEN-METAL EXCHANGE - A NEW ROUTE TO PURINE-RING ANALOGS [J].
GROZIAK, MP ;
WEI, LL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3776-3780
[8]  
Kauffmann-Hefner I., 2004, PCT Int. Appl, Patent No. [2004050658, WO 2004050658]
[9]   SYNTHESIS AND ANTICONVULSANT ACTIVITY OF 3H-IMIDAZO[4,5-C]PYRIDAZINE, 1H-IMIDAZO[4,5-D]PYRIDAZINE AND 1H-BENZIMIDAZOLE ANALOGS OF 9-(2-FLUOROBENZYL)-6-METHYLAMINO-9H-PURINE [J].
KELLEY, JL ;
THOMPSON, JB ;
STYLES, VL ;
SOROKO, FE ;
COOPER, BR .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (05) :1423-1428
[10]   SYNTHESIS OF IMIDAZO[4,5-D]PYRIDAZINES .6. NU-TRIAZOLO[4,5-D]PYRIDAZINES PYRAZINO[2,3-D]PYRIDAZINES AND 7H-IMIDAZO[4,5-D]TETRAZOLO[1,5-B]PYRIDAZINE [J].
MARTIN, SF ;
CASTLE, RN .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (01) :93-&