MXPA06003435A

MXPA06003435A - Benzazoles substituidos y uso de los mismos como inhibidores de la cinasa raf.

Benzazoles substituidos y uso de los mismos como inhibidores de la cinasa raf.

Info

Publication number: MXPA06003435A
Authority: MX; Mexico
Prior art keywords: methyl; amino; carboxamide; oxy; benzimidazol
Prior art date: 2003-09-29

Application number

MXPA06003435A

Other languages

English (en)

Spanish (es)

Inventor

Savithri Ramurthy

Original Assignee

Chiron Corp

Priority date

2003-09-29

Filing date

2004-09-29

Publication date

2006-06-20

2004-09-29 Application filed by Chiron Corp filed Critical Chiron Corp

2006-06-20 Publication of MXPA06003435A publication Critical patent/MXPA06003435A/es

Links

108010077182 raf Kinases Proteins 0.000 title claims abstract description 24
102000009929 raf Kinases Human genes 0.000 title claims abstract description 24
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract description 12
239000003112 inhibitor Substances 0.000 title description 13
150000001875 compounds Chemical class 0.000 claims abstract description 159
239000000203 mixture Substances 0.000 claims abstract description 153
206010028980 Neoplasm Diseases 0.000 claims abstract description 42
238000011282 treatment Methods 0.000 claims abstract description 39
201000011510 cancer Diseases 0.000 claims abstract description 27
241000282414 Homo sapiens Species 0.000 claims abstract description 20
241001465754 Metazoa Species 0.000 claims abstract description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
230000000694 effects Effects 0.000 claims abstract description 14
-1 amidoalkyl Chemical group 0.000 claims description 581
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 207
125000000217 alkyl group Chemical group 0.000 claims description 93
229910052739 hydrogen Inorganic materials 0.000 claims description 75
239000001257 hydrogen Substances 0.000 claims description 64
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
125000001072 heteroaryl group Chemical group 0.000 claims description 51
125000003118 aryl group Chemical group 0.000 claims description 50
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 39
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
125000003710 aryl alkyl group Chemical group 0.000 claims description 30
150000002431 hydrogen Chemical group 0.000 claims description 30
125000001207 fluorophenyl group Chemical group 0.000 claims description 28
125000000068 chlorophenyl group Chemical group 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 27
125000000753 cycloalkyl group Chemical group 0.000 claims description 25
239000003795 chemical substances by application Substances 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
229940002612 prodrug Drugs 0.000 claims description 23
239000000651 prodrug Substances 0.000 claims description 23
150000002148 esters Chemical class 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 19
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 19
125000000623 heterocyclic group Chemical group 0.000 claims description 19
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 18
125000004103 aminoalkyl group Chemical group 0.000 claims description 16
125000004799 bromophenyl group Chemical group 0.000 claims description 16
125000004076 pyridyl group Chemical group 0.000 claims description 15
108091000080 Phosphotransferase Proteins 0.000 claims description 14
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
102000020233 phosphotransferase Human genes 0.000 claims description 14
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 12
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000002883 imidazolyl group Chemical group 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
125000002541 furyl group Chemical group 0.000 claims description 9
KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 9
125000001041 indolyl group Chemical group 0.000 claims description 9
125000006501 nitrophenyl group Chemical group 0.000 claims description 9
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
239000005517 L01XE01 - Imatinib Substances 0.000 claims description 8
150000005347 biaryls Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
241001024304 Mino Species 0.000 claims description 7
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 7
235000010290 biphenyl Nutrition 0.000 claims description 7
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 7
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
230000002401 inhibitory effect Effects 0.000 claims description 7
125000000842 isoxazolyl group Chemical group 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000002757 morpholinyl group Chemical group 0.000 claims description 7
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 6
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 6
HSMPSHPWCOOUJH-UHFFFAOYSA-N anilinyl Chemical group [NH]C1=CC=CC=C1 HSMPSHPWCOOUJH-UHFFFAOYSA-N 0.000 claims description 6
239000012965 benzophenone Substances 0.000 claims description 6
239000004305 biphenyl Substances 0.000 claims description 6
229960004316 cisplatin Drugs 0.000 claims description 6
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 6
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims description 6
DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
229960002949 fluorouracil Drugs 0.000 claims description 6
229940088597 hormone Drugs 0.000 claims description 6
239000005556 hormone Substances 0.000 claims description 6
125000006303 iodophenyl group Chemical group 0.000 claims description 6
229960004768 irinotecan Drugs 0.000 claims description 6
125000003884 phenylalkyl group Chemical group 0.000 claims description 6
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 6
229960004641 rituximab Drugs 0.000 claims description 6
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
229930192474 thiophene Natural products 0.000 claims description 6
QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 claims description 6
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims description 5
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 5
229940123237 Taxane Drugs 0.000 claims description 5
229940122803 Vinca alkaloid Drugs 0.000 claims description 5
229940045799 anthracyclines and related substance Drugs 0.000 claims description 5
229960004397 cyclophosphamide Drugs 0.000 claims description 5
VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 claims description 5
235000008191 folinic acid Nutrition 0.000 claims description 5
239000011672 folinic acid Substances 0.000 claims description 5
229960005277 gemcitabine Drugs 0.000 claims description 5
SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 5
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 5
229960002411 imatinib Drugs 0.000 claims description 5
229960001691 leucovorin Drugs 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
GFFXZLZWLOBBLO-ASKVSEFXSA-N tezacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 GFFXZLZWLOBBLO-ASKVSEFXSA-N 0.000 claims description 5
229950006410 tezacitabine Drugs 0.000 claims description 5
229960000303 topotecan Drugs 0.000 claims description 5
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 5
229960000575 trastuzumab Drugs 0.000 claims description 5
125000004360 trifluorophenyl group Chemical group 0.000 claims description 5
206010006187 Breast cancer Diseases 0.000 claims description 4
208000026310 Breast neoplasm Diseases 0.000 claims description 4
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 4
229960004562 carboplatin Drugs 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 3
230000001419 dependent effect Effects 0.000 claims description 2
201000005787 hematologic cancer Diseases 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 4
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 4
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 2
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 2
RNTCWULFNYNFGI-UHFFFAOYSA-N 1-(2,3-dihydroindol-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)CCC2=C1 RNTCWULFNYNFGI-UHFFFAOYSA-N 0.000 claims 1
206010060862 Prostate cancer Diseases 0.000 claims 1
208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
125000005037 alkyl phenyl group Chemical group 0.000 claims 1
239000002131 composite material Substances 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
238000000034 method Methods 0.000 abstract description 43
230000005764 inhibitory process Effects 0.000 abstract description 8
230000001404 mediated effect Effects 0.000 abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 463
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 287
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 219
230000015572 biosynthetic process Effects 0.000 description 203
238000003786 synthesis reaction Methods 0.000 description 174
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 151
239000000243 solution Substances 0.000 description 129
238000006243 chemical reaction Methods 0.000 description 109
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 109
235000019439 ethyl acetate Nutrition 0.000 description 101
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 94
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 92
IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 91
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 84
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 78
239000012044 organic layer Substances 0.000 description 73
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
239000007787 solid Substances 0.000 description 63
ATHHXGZTWNVVOU-UHFFFAOYSA-N monomethyl-formamide Natural products CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 59
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 56
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 49
229910052757 nitrogen Inorganic materials 0.000 description 49
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 42
239000000047 product Substances 0.000 description 41
239000012267 brine Substances 0.000 description 40
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 40
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 37
239000011541 reaction mixture Substances 0.000 description 37
150000003857 carboxamides Chemical class 0.000 description 36
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 36
238000004237 preparative chromatography Methods 0.000 description 35
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
239000002253 acid Substances 0.000 description 34
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 34
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 29
125000003944 tolyl group Chemical group 0.000 description 29
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 26
238000000746 purification Methods 0.000 description 26
238000003756 stirring Methods 0.000 description 26
239000000725 suspension Substances 0.000 description 25
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 23
230000002829 reductive effect Effects 0.000 description 23
229910052938 sodium sulfate Inorganic materials 0.000 description 23
235000011152 sodium sulphate Nutrition 0.000 description 23
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 19
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 19
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 18
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 17
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 17
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 16
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 16
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
239000002904 solvent Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000012298 atmosphere Substances 0.000 description 15
150000004985 diamines Chemical class 0.000 description 15
229910000027 potassium carbonate Inorganic materials 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
239000008346 aqueous phase Substances 0.000 description 14
239000010410 layer Substances 0.000 description 14
229910052763 palladium Inorganic materials 0.000 description 14
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
150000001412 amines Chemical class 0.000 description 13
238000004128 high performance liquid chromatography Methods 0.000 description 13
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 13
235000011181 potassium carbonates Nutrition 0.000 description 13
102000016914 ras Proteins Human genes 0.000 description 13
108010014186 ras Proteins Proteins 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 11
125000005843 halogen group Chemical group 0.000 description 11
238000004007 reversed phase HPLC Methods 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
229940086542 triethylamine Drugs 0.000 description 11
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
230000003197 catalytic effect Effects 0.000 description 10
125000005842 heteroatom Chemical group 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 10
125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 9
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