AU2004315876B2 - Pyrazolopyridines and analogs thereof - Google Patents

Info

Publication number

AU2004315876B2

AU2004315876B2 AU2004315876A AU2004315876A AU2004315876B2 AU 2004315876 B2 AU2004315876 B2 AU 2004315876B2 AU 2004315876 A AU2004315876 A AU 2004315876A AU 2004315876 A AU2004315876 A AU 2004315876A AU 2004315876 B2 AU2004315876 B2 AU 2004315876B2

Authority

AU

Australia

Prior art keywords

group

alkyl

amino

formula

ethyl

Prior art date

2003-10-03

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

• Espacenet
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• 150000005229 pyrazolopyridines Chemical class 0.000 title description 2
• -1 nitro, hydroxy, mercapto Chemical group 0.000 claims description 433
• 125000000217 alkyl group Chemical group 0.000 claims description 258
• 150000001875 compounds Chemical class 0.000 claims description 223
• 229910052739 hydrogen Inorganic materials 0.000 claims description 150
• 239000001257 hydrogen Substances 0.000 claims description 148
• 125000005466 alkylenyl group Chemical group 0.000 claims description 131
• 125000003118 aryl group Chemical group 0.000 claims description 130
• 125000001072 heteroaryl group Chemical group 0.000 claims description 126
• 125000000623 heterocyclic group Chemical group 0.000 claims description 125
• 150000003839 salts Chemical class 0.000 claims description 117
• 125000002947 alkylene group Chemical group 0.000 claims description 107
• 125000003342 alkenyl group Chemical group 0.000 claims description 86
• 238000000034 method Methods 0.000 claims description 81
• 125000000304 alkynyl group Chemical group 0.000 claims description 66
• 125000001424 substituent group Chemical group 0.000 claims description 58
• 229910052736 halogen Inorganic materials 0.000 claims description 57
• 125000003545 alkoxy group Chemical group 0.000 claims description 53
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
• 125000000732 arylene group Chemical group 0.000 claims description 51
• 150000002367 halogens Chemical class 0.000 claims description 50
• 229910052757 nitrogen Inorganic materials 0.000 claims description 48
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 44
• 125000001188 haloalkyl group Chemical group 0.000 claims description 42
• 125000005549 heteroarylene group Chemical group 0.000 claims description 41
• 125000004450 alkenylene group Chemical group 0.000 claims description 40
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 40
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 39
• 125000004419 alkynylene group Chemical group 0.000 claims description 38
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
• 125000004043 oxo group Chemical group O=* 0.000 claims description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
• 102000004127 Cytokines Human genes 0.000 claims description 28
• 108090000695 Cytokines Proteins 0.000 claims description 28
• 241001465754 Metazoa Species 0.000 claims description 28
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 28
• 125000004104 aryloxy group Chemical group 0.000 claims description 27
• 201000010099 disease Diseases 0.000 claims description 27
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 27
• 125000005842 heteroatom Chemical group 0.000 claims description 26
• 125000004414 alkyl thio group Chemical group 0.000 claims description 25
• 229920006395 saturated elastomer Polymers 0.000 claims description 25
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 23
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
• 230000015572 biosynthetic process Effects 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 125000003282 alkyl amino group Chemical group 0.000 claims description 18
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 17
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 230000003612 virological effect Effects 0.000 claims description 11
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• 230000001613 neoplastic effect Effects 0.000 claims description 9
• LJCJRRKKAKAKRV-UHFFFAOYSA-N (2-amino-2-methylpropyl) 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical group CC(C)(N)COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 LJCJRRKKAKAKRV-UHFFFAOYSA-N 0.000 claims description 7
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 5
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 230000001939 inductive effect Effects 0.000 claims description 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 23
• 230000001419 dependent effect Effects 0.000 claims 4
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 380
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 146
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 105
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
• 239000000243 solution Substances 0.000 description 102
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
• 150000002431 hydrogen Chemical class 0.000 description 89
• 230000002829 reductive effect Effects 0.000 description 88
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 86
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 86
• 239000002904 solvent Substances 0.000 description 85
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 82
• 238000007796 conventional method Methods 0.000 description 82
• 239000000047 product Substances 0.000 description 82
• 239000007787 solid Substances 0.000 description 78
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
• 239000000203 mixture Substances 0.000 description 71
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 70
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 50
• LONFHWIJSLLRRX-UHFFFAOYSA-N 3h-pyrazolo[3,4-c]quinoline Chemical compound C1=CC=C2C3=CNN=C3C=NC2=C1 LONFHWIJSLLRRX-UHFFFAOYSA-N 0.000 description 48
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
• 238000001914 filtration Methods 0.000 description 45
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 43
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
• 229910000029 sodium carbonate Inorganic materials 0.000 description 41
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 38
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
• 238000004587 chromatography analysis Methods 0.000 description 32
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 229960000583 acetic acid Drugs 0.000 description 30
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 30
• 238000010992 reflux Methods 0.000 description 29
• 239000002244 precipitate Substances 0.000 description 25
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 24
• 239000003153 chemical reaction reagent Substances 0.000 description 24
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
• 235000019341 magnesium sulphate Nutrition 0.000 description 24
• 239000003921 oil Substances 0.000 description 24
• 235000019198 oils Nutrition 0.000 description 24
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 24
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 23
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 21
• 239000002585 base Substances 0.000 description 21
• 239000000463 material Substances 0.000 description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• 239000013078 crystal Substances 0.000 description 20
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 19
• 150000001412 amines Chemical class 0.000 description 19
• 239000000908 ammonium hydroxide Substances 0.000 description 19
• 239000012043 crude product Substances 0.000 description 19
• 239000012299 nitrogen atmosphere Substances 0.000 description 19
• 235000011056 potassium acetate Nutrition 0.000 description 19
• 230000004048 modification Effects 0.000 description 18
• 238000012986 modification Methods 0.000 description 18
• 238000000746 purification Methods 0.000 description 18
• 238000010189 synthetic method Methods 0.000 description 18
• MGLHICIVLQDMID-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-pyrazolo[3,4-c]quinoline Chemical compound C1=CC=CC2=C3CNNC3CN=C21 MGLHICIVLQDMID-UHFFFAOYSA-N 0.000 description 17
• 239000000284 extract Substances 0.000 description 17
• 150000002576 ketones Chemical class 0.000 description 17
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
• 238000010438 heat treatment Methods 0.000 description 16
• KOPFEFZSAMLEHK-UHFFFAOYSA-M 1h-pyrazole-5-carboxylate Chemical compound [O-]C(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-M 0.000 description 15
• 230000002452 interceptive effect Effects 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
• 229910052794 bromium Inorganic materials 0.000 description 14
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 229910052938 sodium sulfate Inorganic materials 0.000 description 14
• 235000011152 sodium sulphate Nutrition 0.000 description 14
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
• YMJLEPMVGQBLHL-UHFFFAOYSA-N 1h-pyrazole-5-carbonitrile Chemical compound N#CC1=CC=NN1 YMJLEPMVGQBLHL-UHFFFAOYSA-N 0.000 description 13
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
• 238000005859 coupling reaction Methods 0.000 description 13
• WPDASZCYRKGSTO-UHFFFAOYSA-N (2-aminophenyl)boronic acid;hydrochloride Chemical compound Cl.NC1=CC=CC=C1B(O)O WPDASZCYRKGSTO-UHFFFAOYSA-N 0.000 description 12
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• 238000011282 treatment Methods 0.000 description 12
• 238000010626 work up procedure Methods 0.000 description 12
• 229940044613 1-propanol Drugs 0.000 description 11
• FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical class C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 11
• 230000002378 acidificating effect Effects 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• 239000000706 filtrate Substances 0.000 description 11
• 238000004519 manufacturing process Methods 0.000 description 11
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
• BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 10
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 10
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 10
• 102100040247 Tumor necrosis factor Human genes 0.000 description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
• 230000028993 immune response Effects 0.000 description 10
• 239000012044 organic layer Substances 0.000 description 10
• 235000009518 sodium iodide Nutrition 0.000 description 10
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 10
• 229910052740 iodine Inorganic materials 0.000 description 9
• 239000010502 orange oil Substances 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
• 235000019502 Orange oil Nutrition 0.000 description 8
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 238000006069 Suzuki reaction reaction Methods 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 125000004122 cyclic group Chemical group 0.000 description 8
• 239000000741 silica gel Substances 0.000 description 8
• 229910002027 silica gel Inorganic materials 0.000 description 8
• 159000000000 sodium salts Chemical class 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 229910052723 transition metal Inorganic materials 0.000 description 8
• 150000003624 transition metals Chemical class 0.000 description 8
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 7
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 7
• 239000012346 acetyl chloride Substances 0.000 description 7
• 150000001408 amides Chemical class 0.000 description 7
• 125000003277 amino group Chemical group 0.000 description 7
• 230000008878 coupling Effects 0.000 description 7
• 238000010168 coupling process Methods 0.000 description 7
• 238000006880 cross-coupling reaction Methods 0.000 description 7
• WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 7
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
• 239000005457 ice water Substances 0.000 description 7
• 150000002825 nitriles Chemical group 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• 230000009467 reduction Effects 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 7
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
• 206010028980 Neoplasm Diseases 0.000 description 6
• 150000001299 aldehydes Chemical class 0.000 description 6
• 238000004458 analytical method Methods 0.000 description 6
• 150000008064 anhydrides Chemical class 0.000 description 6
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• 238000010511 deprotection reaction Methods 0.000 description 6
• 239000012362 glacial acetic acid Substances 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• 239000012948 isocyanate Substances 0.000 description 6
• 150000002513 isocyanates Chemical class 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 6
• QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 6
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
• 150000001241 acetals Chemical class 0.000 description 5
• 150000001350 alkyl halides Chemical class 0.000 description 5
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 5
• 235000013877 carbamide Nutrition 0.000 description 5
• 150000001805 chlorine compounds Chemical class 0.000 description 5
• 238000011097 chromatography purification Methods 0.000 description 5
• 150000004820 halides Chemical class 0.000 description 5
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