Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-04-26
1995-08-01
Haley, Jacqueline
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
5483164, C07D23384, C07C23108
Patent
active
054381509
ABSTRACT:
The present invention relates to a process for preparing a 5-(N-substituted)aminomethyl-1-benzocycloalkyl-1,3-dihydroimidazole-2-thio ne (wherein the N-substituent is selected from formyl, aminocarbonyl, (C.sub.1-4)alkylcarbonyl or trifluoro (C.sub.1-4)alkylcarbonyl), which process comprises reacting a benzocycloalkylamine with thiocyanic acid and dihydroxyacetone to give a corresponding 5-hydroxymethyl-1-benzocycloalkyl-1,3-dihydroimidazole-2-thione and then reacting the 5-hydroxymethyl-1-benzocycloalkyl-1,3-dihydroimidazole-2-thione with a compound of the formula H.sub.2 NC(0)R.sup.2 in which R.sup.2 is hydrogen, amino, (C.sub.1-4)alkyl or trifluoro(C.sub.1-4)alkyl or with an ammonium salt of the formula NH.sub.4.sup.+ - OC(0)R.sup.3 in which R.sup.3 is hydrogen, (C.sub.1-4)alkyl or trifluoro(C.sub.1-4)alkyl.
The present invention also relates to a process for preparing 5-aminomethyl-1-benzocycloalkyl-1,3-dihydroimidazole-2-thiones, which process comprises preparing a 5-(N-substituted)aminomethyl-1-benzocycloalkyl-1,3-dihydroimidazole-2-thio ne (wherein the N-substituent is selected from formyl, (C.sub.1-4)alkylcarbonyl or trifluoro(C.sub.1-4)alkylcarbonyl) by the process described above and then hydrolyzing with acid.
REFERENCES:
patent: 5051409 (1991-09-01), Zipplies et al.
patent: 5338862 (1994-08-01), Aiman et al.
March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Fourth Edition, 1992, McGraw-Hill, New York, p. 425.
Duncia, J. V.; Chiu, A. T.; Carini, D. J.; Gregory, G. B.; Johnson, A. L.; Price, W. A.; Wells, G. J.; Wong, P. C.; Calabrese, J. C.; Timmermans, P. B. M. W. M. The Discovery of Potent Nonpeptide Angiotensin II Receptor Antagonists: a New Class of Potent Antihypertensives. J. Med. Chem. 1990, 33, 1312.
Norlander, E. J.; Payne, M. J.; Njoroge, F. G.; Vishwanath, V. M.; Han, G. R., Laikos, G. D., Balk, M. A. A Short Enantiospecific Synthesis of 2-Amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (ADTN). J. Org. Chem. 1985, 50, 3619.
Bansal Rekha P.
Gooding Owen W.
Muehldorf Alexander V.
O'Yang Counde
Haley Jacqueline
Montgomery Wayne W.
Syntex (U.S.A.) Inc.
LandOfFree
Process for making 1-benzocycloalkyl-1,3-dihydroimidazole-2-thio does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for making 1-benzocycloalkyl-1,3-dihydroimidazole-2-thio, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for making 1-benzocycloalkyl-1,3-dihydroimidazole-2-thio will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-734565