DK2013835T3 - Fremstilling af chirale amider og aminer - Google Patents

Fremstilling af chirale amider og aminer Download PDF

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DK2013835T3
DK2013835T3 DK07759847.2T DK07759847T DK2013835T3 DK 2013835 T3 DK2013835 T3 DK 2013835T3 DK 07759847 T DK07759847 T DK 07759847T DK 2013835 T3 DK2013835 T3 DK 2013835T3
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substituted
unsubstituted
alkyl
enamide
formula
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Stefan G Koenig
Charles P Vandenbossche
Surendra P Singh
Scott H Wilkenson
Roger P Bakale
Hang Zhao
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Sunovion Pharmaceuticals Inc
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Claims (9)

1. Fremgangsmåde til omdannelse af et oxim til et enamid, hvilken fremgangsmåde omfatter: (a) etablering af kontakt mellem oximet og et phosphin og en acyldonor under forhold egnede til at omdanne oximet til enamidet; hvor oximet har formlen:
hvor R1, R2 og R3 er elementer uafhængigt udvalgt fra H, substitueret eller usubstitueret alkyl, substitueret eller usubstitueret heteroalkyl, substitueret eller usubstitueret aryl, substitueret eller usubstitueret heteroaryl og substitueret eller usubstitueret heterocycloalkyl, og mindst to af R1, R2 og R3 eventuelt er samlet for at danne et ringsystem udvalgt lfa substitueret eller usubstitueret cycloalkyl, substitueret eller usubstitueret heterocycloalkyl, substitueret eller usubstitueret aryl og substitueret eller usubstitueret heteroaryl; hvor acyldonoren har formlen: Z-C(0)-R5 hvor R5 er et element udvalgt lfa H, substitueret eller usubstitueret alkyl, substitueret eller usubstitueret heteroalkyl, substitueret eller usubstitueret aryl, substitueret eller usubstitueret heteroaryl og substitueret eller usubstitueret heterocycloalkyl, hvor Z-C(0)-R5 er et syrechlorid (Z=C1) eller en N-hydroxysuccinimidylester, eller hvor Z har formlen: R6-C(0)-0- hvor R6 er et element udvalgt lfa substitueret eller usubstitueret alkyl, substitueret eller usubstitueret heteroalkyl, substitueret eller usubstitueret aryl, substitueret eller usubstitueret heteroaryl og substitueret eller usubstitueret heterocycloalkyl, hvor eventuelt både R5 og R6 er uafhængigt udvalgte, substituerede eller usubstituerede CrC4-dele; hvor termen ‘ ‘alkyl’ ’ omfatter en lige eller forgrenet kæde eller cyklisk carbonhydridradikal eller kombination deraf, der kan være fuldt mættet, mono- eller polyumættet og kan indbefatte mono-, di- og multivalente radikaler; hvor substituenteme for alkyl-, heteroalkyl-, cycloalkyl- og heterocycloalkylradikaleme omfatter en gruppe udvalgt fra gruppen bestående af: -OR’, =0, =NR’, =N-OR’, -NR’R’ ’, -SR’, -halogen, -SiR’R”R”, -0C(0)R’, -C(0)R’, -C02R’, -CONR’R”, -0C(0)NR’R”, -NR”C(0)R’, -NR’ -C(0)NR”R”\ -NR”C(0)2R\ -NR-C(NR,R”R’”)=NR””, -NR-C(NR,R”)=NR’”, -S(0)R\ -S(0)2R’, -S(0)2NR’R”, -NRS02R’, -CN og -N02i et antal fra nul til (2m’+ 1), hvor m’ er det samlede antal af carbonatomer i en sådan radikal; hvor R’, R”, R’” og R”” hver uafhængigt er hydrogen, usubstitueret heteroalkyl, usubstitueret aryl, usubstitueret alkyl, alkoxy eller thioalkoxygrupper eller arylalkylgrupper; hvor substituenteme for aryl- og heteroarylradikaleme omfatter en gruppe udvalgt fra gruppen bestående af: halogen, -OR’, =0, =NR’, =N-OR\ -NR’R” -SR’ -SiR’R”R’” -0C(0)R’ -C(0)R’ -C02R’ -CONR’R” -0C(0)NR’R, -NR”C(0)R’, -NR’-C(0)NR”R”\ -NR”C(0)2R’, -NR-C(NR’R”R”’)=NR””, -NR-C(NR’R”)=NR’”, -S(0)R\ -S(0)2R’, -S(0)2NR’R”, -NRS02R’, -CN og -N02, -R’, -N3, -CH(Ph)2, fluor(Ci-C4)-alkoxy og fluor(Ci-C4)-alkyl, i et antal fra nul til det samlede antal af åbne valenser på det aromatiske ringsystem; og hvor R’, R”, R’” og R”” hver uafhængigt er hydrogen, usubstitueret alkyl, usubstitueret heteroalkyl, usubstitueret aryl og usubstitueret heteroaryl.
2. Fremgangsmåde ifølge krav 1, hvor oximet har formlen:
hvor Ar er et element udvalgt fra substitueret eller usubstitueret aryl og substitueret eller usubstitueret heteroaryl; R4 er et element udvalgt fra H, substitueret eller usubstitueret alkyl, substitueret eller usubstitueret heteroalkyl, substitueret eller usubstitueret aryl, substitueret eller usubstitueret heteroaryl og substitueret eller usubstitueret heterocycloalkyl; og a er udvalgt fra heltallene fra 1 til 4, eventuelt hvor R4 er substitueret eller usubstitueret aryl, f.eks. substitueret eller usubstitueret phenyl såsom, for eksempel, phenyl substitueret med mindst ét halogen; hvor termen ’’alkyl” omfatter en lige eller forgrenet kæde eller cyklisk carbonhydridradikal eller kombination deraf, der kan være fuldt mættet, mono- eller polyumættet og kan indbefatte mono-, di- og multivalente radikaler; hvor substituenteme for alkyl-, heteroalkyl- og heterocycloalkylradikaleme omfatter en gruppe udvalgt fra gruppen bestående af: -OR’, =0, =NR’, =N-OR’, -NR’R”, -SR’, - halogen, -SiR’R”R”, -0C(0)R’, -C(0)R\ -C02R\ -CONR’R”, -0C(0)NR’R”, -NR”C(0)R\ -NR’ -C(0)NR”R”’, -NR”C(0)2R’, -NR-C(NR’R”R’”)=NR””, -NR-C(NR’R”)=NR”\ -S(0)R’, -S(0)2R\ -S(0)2NR’R”, -NRSO2R’, -CN og -NO2 i et antal fra nul til (2m’+ 1), hvor m’ er det samlede antal af carbonatomer i en sådan radikal; hvor R’, R”, R’” og R”“ hver uafhængigt er hydrogen, usubstitueret heteroalkyl, usubstitueret aryl, usubstituerede alkyl-, alkoxy- eller thioalkoxygrupper eller arylalkylgrupper; hvor substituenteme for aryl- og heteroarylradikaleme omfatter en gruppe udvalgt fra gruppen bestående af: halogen, -OR’, =0, =NR\ =N-OR\ -NR’R” -SR’ -SiR’R”R”‘ -0C(0)R’ -C(0)R’ -C02R’ -CONR’R” -0C(0)NR’R, -NR”C(0)R’, -NR’-C(0)NR”R”’, -NR”C(0)2R’, -NR- C(NR’R”R’”)=NR””, -NR-C(NR,R”)=NR’”, -S(0)R\ -S(0)2R\ -S^NR’R”, -NRS02R’, -CN og -NO2, -R’, -N3, -CH(Ph)2, fluor(Ci-C4)-alkoxy og fluor(Ci-C4)-alkyl, i et antal fra nul til det samlede antal af åbne valenser på det aromatiske ringsystem; og hvor R’, R”, R’” og R”“ hver uafhængigt er hydrogen, usubstitueret alkyl, usubstitueret heteroalkyl, usubstitueret aryl og usubstitueret heteroaryl. Fremgangsmåde ifølge krav 2, hvor R4 har formlen:
hvor X1 og X2 hver uafhængigt er halo, eventuelt begge er chlor. Fremgangsmåde ifølge krav 2 eller krav 3, hvor Ar er substitueret eller usubstitueret phenyl. Fremgangsmåde ifølge krav 4, hvor oximet har formlen:
i. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor phosphinet har formlen: P(Q)3 hvor hvert Q er et element uafhængigt udvalgt fra H, substitueret eller usubstitueret alkyl og substitueret eller usubstitueret aryl, eventuelt hvor hvert Q er et element uafhængigt udvalgt fra substitueret eller usubstitueret Ci-C6-alkyl; hvor termen ’’alkyl” omfatter en lige eller forgrenet kæde eller cyklisk carbonhydridradikal eller kombination deraf, der kan være fuldt mættet, mono- eller polyumættet og kan indbefatte mono-, di- og multivalente radikaler; hvor substituenteme for alkylradikaleme omfatter en gruppe udvalgt fra gruppen bestående af: -OR’, =0, =NR’, =N-OR’, -NR’R”, -SR’, -halogen, -SiR’R”R”, -0C(0)R’, -C(0)R’, -C02R\ -CONR’R”, -0C(0)NR’R”, -NR”C(0)R’, -NR’ -C(0)NR”R”’, -NR”C(0)2R’, -NR-C(NR’R”R’”)=NR””, -NR-C(NR’R”)=NR”\ -S(0)R’, -S(0)2R’, -S(0)2NR’R”, -NRS02R’, -CN og -N02 i et antal fra nul til (2m’+ 1), hvor m’ er det samlede antal carbonatomer i en sådan radikal; hvor R’, R”, R’” og R”” hver uafhængigt er hydrogen, usubstitueret heteroalkyl, usubstitueret aryl, usubstitueret alkyl-, alkoxy- eller thioalkoxygrupper eller arylalkylgrupper; hvor substituenteme for arylradikaleme omfatter en gruppe udvalgt fra gruppen bestående af: halogen, -OR’, =0, =NR’, =N-OR’, -NR’R” -SR’ -SiR’R”R’” -0C(0)R’ -C(0)R’ -C02R’ -CONR’R” -0C(0)NR’R, -NR”C(0)R’, -NR’-C(0)NR”R”’, -NR”C(0)2R’, -NR- C(NR’R”R’”)=NR””, -NR-C(NR’R”)=NR’”, -S(0)R’, -S(0)2R’, -S(0)2NR’R”, -NRS02R’, -CN og -N02, -R’, -N3, -CH(Ph)2, fluor(Ci-C4)-alkoxy, og fluor(Ci-C4)-alkyl, i et antal fra nul til det samlede antal åbne valenser på det aromatiske ringsystem; og hvor R’, R”, R’” og R”” hver uafhængigt er hydrogen, usubstitueret alkyl, usubstitueret heteroalkyl, usubstitueret aryl og usubstitueret heteroaryl.
7. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvor etableringen af kontakt sker i opløsning med et aprotisk opløsningsmiddel, eventuelt hvor det aprotiske opløsningsmiddel er et aromatisk opløsningsmiddel, f.eks. er udvalgt fra toluen, xylen og kombinationer deraf.
8. Fremgangsmåde ifølge krav 6 eller krav 7, hvor enamidet har formlen:
eventuelt hvor C-4 har en konfiguration udvalgt fra R, S og blandinger deraf, f.eks. er af S-konfiguration.
9. Fremgangsmåde ifølge et hvilket som helst af de foregående krav, hvilken fremgangsmåde endvidere omfatter: (b) etablering af kontakt mellem enamidet dannet i trin (a) og en hydrogenisationkatalysator og hydrogen- eller hydrogenoverførselsreagens under forhold egnet til hydrogenisere en carbon-carbondobbeltbinding af enamidet, hvorved enamidet omdannes til et amid, eventuelt hvor katalysatoren er en chiral katalysator, f.eks. et kompleks af et transitionsmetal med en chiral phosphinligand, og/eller hvor amidet er et racemisk eller chiralt amid, f.eks. hvor amidet har formlen:
eventuelt hvor C-i og C-4 har en konfiguration uafhængigt udvalgt fra R og S, f.eks. hvor C-l er af ^-Configuration; og C-4 er af 5-konfiguration.
10. Fremgangsmåde ifølge krav 9, hvilken fremgangsmåde endvidere omfatter: (c) etablering af kontakt mellem amidet og et deacylerende reagens under forhold egnet til at deacylere -HNC(0)R5 af amidet, hvorved der dannes et amin, hvilken fremgangsmåde eventuelt endvidere omfatter: (d) isolering af aminet, eventuelt hvor isoleringen omfatter selektiv krystallisering og/eller aminet har formlen:
hvor Q' er et anion; og e er 0 til 1, eventuelt hvor C-l og C-4 har en konfiguration uafhængigt udvalgt fra R og S~ f.eks. hvor C-l er af R-konfiguration; og C-4 er af ^-konfiguration.
11. Fremgangsmåde ifølge krav 1, hvor fremgangsmåden involverer omdannelse af et oxim, der har formlen
til et enamid, der har formlen:
hvor R4 er udvalgt fra substitueret eller usubstitueret aryl og substitueret eller usubstitueret heteroaryl; og R5 er udvalgt fra H, substitueret eller usubstitueret alkyl, substitueret eller usubstitueret heteroalkyl, substitueret eller usubstitueret aryl, substitueret eller usubstitueret heteroaryl og substitueret eller usubstitueret heterocycloalkyl, hvilken fremgangsmåde omfatter: (a) etablering af kontakt mellem oximet og et phosphin og en acyldonor under forhold egnet til at omdanne oximet til enamidet.
12. Fremgangsmåde ifølge krav 11, hvor C-4 er af S-konfiguration, og/eller phosphinet er et trialkylphosphin, og/eller hvor oximet, acyldonoren og phosphinet er opløst i et aromatisk opløsningsmiddel, og/eller hvor acyldonoren er et alkylanhydrid.
13. Fremgangsmåde ifølge krav 11 eller krav 12, hvilken fremgangsmåde endvidere omfatter: (b) etablering af kontakt mellem enamidet dannet i trin (a) og en chiral hydrogenisationskatalysator og hydrogen under forhold egnet til at hydrogenisere en carbon-carbondobbeltbinding konjugeret til C(O) af enamidet, hvorved enamidet omdannes til et amid, der har formlen:
hvor C-l har en konfiguration udvalgt fra R og S, eventuelt hvor den chirale katalysator omfatter rhodium kompleksdannet til en chiral phosphinligand, og hvilken fremgangsmåde eventuelt endvidere omfatter: (c) etablering af kontakt mellem amidet og et deacylerende reagens under forhold egnet at deacylere -HNC(0)R5 af amidet, hvorved der dannes et amin, der har formlen:
hvor Q" er en anion; og e er 0 eller 1, eventuelt hvor det deacylerende reagens er et enzym eller er en syre.
DK07759847.2T 2006-03-31 2007-03-30 Fremstilling af chirale amider og aminer DK2013835T3 (da)

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JP2013079249A (ja) 2013-05-02
JP2015155450A (ja) 2015-08-27
PT2816024T (pt) 2017-10-20
US8524950B2 (en) 2013-09-03
HK1125356A1 (en) 2009-08-07
US20120095106A1 (en) 2012-04-19
US20090149549A1 (en) 2009-06-11
US20180016224A1 (en) 2018-01-18
HK1200807A1 (en) 2015-08-14
ES2555315T3 (es) 2015-12-30
US20160016891A1 (en) 2016-01-21
US20140057990A1 (en) 2014-02-27
CA2648121C (en) 2013-08-06
WO2007115185A2 (en) 2007-10-11
EP2816024A1 (en) 2014-12-24
JP5377285B2 (ja) 2013-12-25

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