A solid phase traceless synthesis of 2-arylaminobenzimidazoles

Tetrahedron Letters

Volumn 42, Issue 9, 2001, Pages 1627-1630

  Krchñák, Viktor ^a   Smith, Jennifer ^a   Vágner, Josef ^a  

^a SIDDCO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOBENZIMIDAZOLE DERIVATIVE; 2 NITROBENZENE DERIVATIVE; 2 PHENYLENE DIAMINE; 4 METHYLBENZHYDRYLAMINE; ACID; ANILINE DERIVATIVE; BENZENE DERIVATIVE; CYANAMIDE; DIAMINE DERIVATIVE; HALIDE; IMIDAZOLE DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE; N BENZYLANILINE DERIVATIVE; NITRO DERIVATIVE; REAGENT; RESIN; THIOUREA; TIN CHLORIDE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DERIVATIZATION; GAS; REACTION ANALYSIS; REDUCTION; SOLID; STOICHIOMETRY; SYNTHESIS;

EID: 0035951929     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)02349-2     Document Type: Article

References (15)

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2. Krchňák V., Szabo L., Vágner J. Tetrahedron Lett. 41:2000;2835-2838.
3. Krchňák, V.; Smith, J.; Vágner, J. accepted for publication.
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10. Kerschen A., Kaniszai A., Botros I., Krchňák V. J. Comb. Chem. 1:1999;480-484.
11. Domino Block (Torviq, Tucson, AZ, www.torviq.com) is a simple manual solid phase synthesizer that allows parallel synthesis of up to 48 compounds using plastic syringes equipped with a frit as reaction vessels. Krchňák, V.; Padera, V. Bioorg. Med. Chem. Lett. 1998, 8, 3261-3264.
12. Analytical gradient HPLC profile was run on a ProC18 4.6×50 mm analytical column (YMC, Wilmington, NC), gradient 0-70% of ACN in 7 min. The purity was estimated based on analytical traces at 280 nm.
13. 6) of compound 5a δ: 7.27 (t, 2 H), 7.44 (d, 1H), 7.49 (d, 1H), 7.61 (s, 1H), 7.67 (q, 2H); compound 5c δ: 7.11 (t, 1H), 7.26 (m, 1H), 7.34 (d, 1H), 7.4 (m, 2H), 7.50 (m, 1H), 7.63 (s, 1H); compound 5d δ: 2.33 (s, 3H), 7.06 (t, 1H), 7.23 (d, 1H), 7.34 (d, 2H), 7.38 (q, 1H), 7.43 (d, 1H), 7.66 (s, 1H). All compounds were measured as TFA or HF salts.
14. Cleavage of alkylated 2-arylaminobenzimidazoles from the resin was carried out in TFA. Exposure to gaseous HF partially cleaved the benzyl group having electron-donating substituents.
15. 3 in water, DIC was added, and the reaction mixture was kept at rt overnight.