http://rdf.ncbi.nlm.nih.gov/pubchem/patent/NZ-333169-A

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filingDate 1996-10-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_5366cdd7a56ae1994fd4e71f5fedc888
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publicationDate 2000-08-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber NZ-333169-A
titleOfInvention Processes for preparing 1H-imidazo[4,5-c]quinolin-4-amines and certain tetrazolo[1,5-c]quinoline intermediates
abstract The process comprises: 1) nitrating a tetrazolo[1,5-a]quinolin-5-ol of formula I to produce a 4-nitro-tetrazolo[1,5-a]quinolin-5-ol compound of formula II; 2) sulphonylating the compound of step 1) to produce 4-nitro-tetrazolo[1,5-a]quinolin-5-ol-5-sulphonate compound of formula III; 3) reacting the compound of step 2) with an amine to produce 4-nitro-tetrazolo[1,5-a]quinolin-5-amine compound of formula IV; 4) reducing the compound of step 3) to produce a tetrazolo[1,5-a]quinolin-4,5-diamine compound of formula V; 5) reacting the compound of formula 4) with carboxylic acid or equivalent thereof to produce a 6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline compound of formula VI; 6) reacting the compound of step 5) with triphenylphosphine to produce a N-triphenylphosphinyl-1H-imidazo[4,5-c]quinolin-4-amine of formula VII; 7) hydrolyzing the compound of step 6) to produce a 1H-imidazo[4,5-c]quinolin-4-amine compound of formula VIII and 8) isolating the 1H-imidazo[4,5-c]quinolin-4-amine compound of formula VIII or pharmaceutically acceptable salt. An alternative to step 1) is to react a 4-amino-2-chloro-3-nitroquinoline with sodium azide to produce a produce 4-nitro-tetrazolo[1,5-a]quinolin-5-amine compound of formula IV; An alternative to steps 1) to 4) is to: a) reacting 4-chloro-1H-imidazo[4,5-c]quinoline with hydrazine to produce a 4-hydrazino- 1H-imidazo[4,5-c]quinoline compound and b) reacting the compound of step a) with sodium nitrate to produce 6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline compound of formula VI.
priorityDate 1996-06-21-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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