DK3122748T3 - Fremgangsmåde til fremstilling af 3-(3-(4-(1-aminocyclobutyl)phenyl)-5-phenyl-3h-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amin - Google Patents

Fremgangsmåde til fremstilling af 3-(3-(4-(1-aminocyclobutyl)phenyl)-5-phenyl-3h-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amin Download PDF

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DK3122748T3
DK3122748T3 DK15770319.0T DK15770319T DK3122748T3 DK 3122748 T3 DK3122748 T3 DK 3122748T3 DK 15770319 T DK15770319 T DK 15770319T DK 3122748 T3 DK3122748 T3 DK 3122748T3
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phenyl
butyl
carbamate
cyclobutyl
amino
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Craig Bates
Jianmin Mao
David P Reed
Jian-Xie Chen
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Arqule Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

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Claims (15)

1. Fremgangsmåde til fremstilling af 3-(3-(4-( 1-aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amin, der omfatter trinnet fra trin 3, omsætning af tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med 2-aminonicotinaldehyd i tilstedeværelse af en oxidant og en syre i et polært protisk opløsningsmiddel for at danne tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat.
2. Fremgangsmåde ifølge krav 1, der omfatter trinnene fra trin 2, behandling af tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med et reducerende middel i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; og trin 3, omsætning af tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med 2-aminonicotinaldehyd i tilstedeværelse af en oxidant og en syre i et polært protisk opløsningsmiddel for at danne tert-butyl (1-(4-(2-(2-aminopyridin-3- yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat, eventuelt hvor i trin 2, det polære aprotiske opløsningsmiddel er tetrahydrofuran eller 2-methyltetrahydrofuran.
3. Fremgangsmåde ifølge krav 2, der omfatter trinnene fra trin 1, omsætning af 2-chlor-3-nitro-6-phenylpyridin med tert-butyl (l-(4-aminophenyl)cyclobutyl)carbamat i tilstedeværelse af en base i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; trin 2, behandling af tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med et reducerende middel i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; og trin 3, omsætning af tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med 2-aminonicotinaldehyd i tilstedeværelse af en oxidant og en syre i et polært protisk opløsningsmiddel for at danne tert-butyl (1-(4-(2-(2-aminopyridin-3- yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat.
4. Fremgangsmåde ifølge krav 2, der omfatter trinnene fra trin la, kobling af 3-nitro-6-phenylpyridin-2-amin med tert-butyl (l-(4-bromphenyl)cyclobutyl)carbamat i tilstedeværelse af en palladiumkatalysator og en phosphorligand i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; trin 2, behandling af tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2- yl)amino)phenyl)cyclobutyl)carbamat med et reducerende middel i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; trin 3, omsætning af tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med 2-aminonicotinaldehyd i tilstedeværelse af en oxidant og en syre i et polært protisk opløsningsmiddel for at danne tert-butyl (1-(4-(2-(2-aminopyridin-3- yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat.
5. Fremgangsmåde ifølge krav 3, der omfatter trinnene fra trin 1, omsætning af 2-chlor-3-nitro-6-phenylpyridin med tert-butyl (l-(4-aminophenyl)cyclobutyl)carbamat i tilstedeværelse af en base i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; trin 2, behandling af tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med et reducerende middel i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; trin 3, omsætning af tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med 2-aminonicotinaldehyd i tilstedeværelse af en oxidant og en syre i et polært protisk opløsningsmiddel for at danne tert-butyl (1-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat; og trin 4, behandling af tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat med en syre i et polært aprotisk opløsningsmiddel for at danne 3-(3-(4-(l-aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amin, eventuelt hvor i trin 4, det polære aprotiske opløsningsmiddel er dichlormethan, eller syren er methansulfonsyre, eller forholdet mellem syren og tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat er ca. 5:1.
6. Fremgangsmåde ifølge krav 4, der omfatter trinnene fra trin la, kobling af 3-nitro-6-phenylpyridin-2-amin med tert-butyl (l-(4-bromphenyl)cyclobutyl)carbamat i tilstedeværelse af en palladium katalysator og en phosphorligand i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; trin 2, behandling af tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med et reducerende middel i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; trin 3, omsætning af tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med 2-aminonicotinaldehyd i tilstedeværelse af en oxidant og en syre i et polært protisk opløsningsmiddel for at danne tert-butyl (1-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat; og trin 4, behandling af tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat med en syre i et polært aprotisk opløsningsmiddel for at danne 3-(3-(4-(l-aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amin.
7. Fremgangsmåde til fremstilling af 3-(3-(4-( 1 -aminocyclobutyl)phenyl)-5-phenyl-3H- imidazo[4,5-b]pyridin-2-yl)pyridin-2-amin, trinnet fra trin 2’, behandling af tert-butyl (1-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med et reducerende middel i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat, erstatning af det polære aprotiske opløsningsmiddel med et polært protisk opløsningsmiddel, og omsætning af tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med 2-aminonicotinaldehyd i tilstedeværelse af en oxidant og en syre i et polært protisk opløsningsmiddel for at danne tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3- yl)phenyl)cyclobutyl)carbamat.
8. Fremgangsmåde ifølge krav 7, der omfatter trinnene fra trin 2’, behandling af tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med et reducerende middel i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat, erstatning af det polære aprotiske opløsningsmiddel med et polært protisk opløsningsmiddel, og omsætning af tert-butyl (1-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med 2- aminonicotinaldehyd i tilstedeværelse af en oxidant og en syre i et polært protisk opløsningsmiddel for at danne tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3- yl)phenyl)cyclobutyl)carbamat; og trin 3’, behandling af tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat med en syre i et polært aprotisk opløsningsmiddel for at danne 3-(3-(4-(l-aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amin, eventuelt hvor i trin 2’, det polære aprotiske opløsningsmiddel er tetrahydrofuran eller 2-methyltetrahydrofuran.
9. Fremgangsmåde ifølge krav 8, der omfatter trinnene fra trin 1, omsætning af 2-chlor-3-nitro-6-phenylpyridin med tert-butyl (l-(4-aminophenyl)cyclobutyl)carbamat i tilstedeværelse af en base i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; trin 2’, behandling af tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2- yl)amino)phenyl)cyclobutyl)carbamat med et reducerende middel i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat, erstatning af det polære aprotiske opløsningsmiddel med et polært protisk opløsningsmiddel, og omsætning af tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med 2-aminonicotinaldehyd i tilstedeværelse af en oxidant og en syre i et polært protisk opløsningsmiddel for at danne tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3- yl)phenyl)cyclobutyl)carbamat; og trin 3’, behandling af tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat med en syre i et polært aprotisk opløsningsmiddel for at danne 3-(3-(4-(l-aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amin, eventuelt hvor i trin 3’, det polære aprotiske opløsningsmiddel er dichlormethan, eller syren er methansulfonsyre, eller forholdet mellem syren og tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat er ca. 5:1.
10. Fremgangsmåde ifølge krav 8, der omfatter trinnene fra trin la, kobling af 3-nitro-6-phenylpyridin-2-amin med tert-butyl (l-(4-bromphenyl)cyclobutyl)carbamat i tilstedeværelse af en palladiumkatalysator og en phosphorligand i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat; trin 2’, behandling af tert-butyl (l-(4-((3-nitro-6-phenylpyridin-2- yl)amino)phenyl)cyclobutyl)carbamat med et reducerende middel i et polært aprotisk opløsningsmiddel for at danne tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat, erstatning af det polære aprotiske opløsningsmiddel med et polært protisk opløsningsmiddel, og omsætning af tert-butyl (l-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamat med 2-aminonicotinaldehyd i tilstedeværelse af en oxidant og en syre i et polært protisk opløsningsmiddel for at danne tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3- yl)phenyl)cyclobutyl)carbamat; og trin 3’, behandling af tert-butyl (l-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamat med en syre i et polært aprotisk opløsningsmiddel for at danne 3- (3-(4-(l-aminocyclobutyl)phenyl)-5-phenyl- 3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amin.
11. Fremgangsmåde ifølge krav 1 eller 7, hvor det polære protiske opløsningsmiddel er methanol, eller syren er eddikesyre, eller forholdet mellem syren og opløsningsmidlet er ca. 9:1.
12. Fremgangsmåde ifølge krav 1 eller 7, hvor oxidanten er luft.
13. Fremgangsmåde ifølge krav 1 eller 7, hvor oxidanten er et/en metal- eller ikke-metalbaseret salt eller katalysator, eventuelt hvor oxidanten er valgt fra gruppen bestående af metalacetat, metalperborat, metalchlorid, palladiumbaseret katalysator og hydrater deraf, eventuelt hvor oxidanten endvidere er valgt fra gruppen bestående af CU(OAc)2*H2O, NaBO3*4H2O, FeCl3*6H2O og 10 % Pd/C og hydrater deraf; eventuelt hvor oxidanten er NaBO3 · 4H2O.
14. Fremgangsmåde ifølge krav 3 eller 9, hvor i trin 1, det polære aprotiske opløsningsmiddel er dimethylacetamid, eller basen er Na2CO3.
15. Fremgangsmåde ifølge krav 4 eller 10, hvor i trin la phosphorliganden er 4,5-bis(diphenylphosphino)-9,9-dimethylxanthen, eller det polære aprotiske opløsningsmiddel er tetrahydrofuran.
DK15770319.0T 2014-03-24 2015-03-24 Fremgangsmåde til fremstilling af 3-(3-(4-(1-aminocyclobutyl)phenyl)-5-phenyl-3h-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amin DK3122748T3 (da)

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