Microwave-assisted three component one-pot synthesis of pyrimido-oxazepines

Tetrahedron Letters

Volumn 48, Issue 8, 2007, Pages 1489-1492

  Hudson, Colleen ^a   Srinivasa Murthy, V ^a   Estep, Kimberly G ^b   Gustafson, Gary ^a  

^a ARQULE INC   (United States)

^b PFIZER INC   (United States)

Author keywords

Microwave; Oxazepines; Three component reaction

Indexed keywords

OXAZEPINE DERIVATIVE; PYRIMIDINONE DERIVATIVE;

ARTICLE; HEATING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICROWAVE RADIATION; ONE POT SYNTHESIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33846400001     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.058     Document Type: Article

References (11)

1. Lange T., and Lindell S. Comb. Chem. High Throughput Screening 8 (2005) 595-606
2. Hadari, Yaron; Smith, Leon M., II. EGFR Tyrosine Kinase Inhibitors and Therapeutic Compositions Containing Them. WO 2005009384, 2005; 208 pp.
3. Pan W., Liu H., Xu Y.-J., Chen X., Kim K., Milligan D., Columbus J., Hadari Y., Kussie P., Wong W., and Labelle M. Bioorg. Med. Chem. Lett. 15 (2005) 5474-5477
4. Tamura K., and Fukuoka M. Expert Opin. Pharmacother. 6 (2005) 985-993
5. Blackhall F., Rehman S., and Thatcher N. Expert Opin. Pharmacother. 6 (2005) 995-1002
6. Xu Y.-J., Liu H., Pan W., Chen X., Wong W., and Labelle M. Tetrahedron Lett. 46 (2005) 7523-7526
7. Duncton M., Smith II L., Burdzovic-Wizeman S., Burns A., Liu H., Mao Y., Wong W., and Kiselyov A. J. Org. Chem. 70 (2005) 9629-9631
8. Smith L., Piatnitski E., Kiselyov A., Ouyang X., Chen X., Burdzovic-Wizemann S., Xu Y., Wang Y., Rosler R., Patel S., Chiang H.-H., Milligan D., Columbus J., Wong W., Doody J., and Hadari Y. Bioorg. Med. Chem. Lett. 16 (2006) 1643-1646
9. 3): δ 160, 155.8, 154.8, 147.3, 130.8, 129.6, 128.7, 124.9, 123.3, 121.4, 49.6, 48, 26.3, 24.6.
10. 3): δ 157.3, 157.2, 148.8, 145.1, 137.4, 132.2, 129.2, 125.7, 122.4, 121.8, 115.1, 114.1, 114, 55.9, 47.5.
11. All reactions were purified using HPLC-MS purification. Equipment: A Maccel semi-prep SH-C18 50 × 20 mm column was used. All compounds were purified using a Shimadzu HPLC system consisting of two LC-8A prep pumps, LC-10ADvp pump, 2 SPD-10A UV detectors, and an SCL-10A system controller. Two Gilson liquid handlers were used for injection and collection and a Waters ZQ mass spectrometer was used for detection. The Masslynx version 4.0 platform controlled the injections and tracked all data outputs. Experimental conditions: Purification was done by RP-HPLC with MS trigger using a gradient of water (solvent A) and acetonitrile (solvent B) with 0.1% TFA and a 2.5 min run time. Molecular weights were detected using positive electrospray ionization mode on the mass spectrometer with a cone voltage of 20 V. These conditions were optimized for individual compounds using varying acetonitrile/water gradients.