BR112012009751A2 - métodos de síntese e purificação de heteroarila - Google Patents

Info

Publication number

BR112012009751A2

BR112012009751A2 BR112012009751-2A BR112012009751A BR112012009751A2 BR 112012009751 A2 BR112012009751 A2 BR 112012009751A2 BR 112012009751 A BR112012009751 A BR 112012009751A BR 112012009751 A2 BR112012009751 A2 BR 112012009751A2

Authority

BR

Brazil

Prior art keywords

pyrazin

dihydropyrazine

methyl

pyridin

triazol

Prior art date

2009-10-26

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 75
• 125000001072 heteroaryl group Chemical group 0.000 title abstract description 36
• 238000000746 purification Methods 0.000 title abstract description 20
• 238000003786 synthesis reaction Methods 0.000 title abstract description 10
• 230000015572 biosynthetic process Effects 0.000 title abstract description 9
• 238000002360 preparation method Methods 0.000 claims abstract description 5
• -1 4- (3-methoxybenzyl) - 3,4-dihydropyrazine Chemical compound 0.000 claims description 483
• HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims description 312
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 217
• 150000001875 compounds Chemical class 0.000 claims description 189
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 168
• 125000000217 alkyl group Chemical group 0.000 claims description 137
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 129
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 109
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 82
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 79
• 239000002904 solvent Substances 0.000 claims description 66
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 60
• 229910052736 halogen Inorganic materials 0.000 claims description 60
• 125000000623 heterocyclic group Chemical group 0.000 claims description 58
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 56
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 52
• 150000002367 halogens Chemical class 0.000 claims description 50
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 47
• 229910052763 palladium Inorganic materials 0.000 claims description 39
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 38
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
• 239000002585 base Substances 0.000 claims description 36
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 35
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 33
• 125000004429 atom Chemical group 0.000 claims description 33
• QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 claims description 31
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
• 150000003839 salts Chemical class 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 28
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 28
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
• 239000003054 catalyst Substances 0.000 claims description 24
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 22
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 22
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 21
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 20
• 229910000029 sodium carbonate Inorganic materials 0.000 claims description 19
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 18
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 18
• 235000017557 sodium bicarbonate Nutrition 0.000 claims description 16
• 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 16
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 13
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 13
• 125000004122 cyclic group Chemical group 0.000 claims description 13
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 11
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 229910052796 boron Inorganic materials 0.000 claims description 9
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 9
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 9
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 8
• 101100113998 Mus musculus Cnbd2 gene Proteins 0.000 claims description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• 238000007363 ring formation reaction Methods 0.000 claims description 7
• 229910052783 alkali metal Inorganic materials 0.000 claims description 6
• 150000007942 carboxylates Chemical class 0.000 claims description 6
• MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 6
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 6
• IQTHEAQKKVAXGV-UHFFFAOYSA-N 4-ditert-butylphosphanyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1 IQTHEAQKKVAXGV-UHFFFAOYSA-N 0.000 claims description 5
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
• KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 5
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• YLWPCUTVHSWTDT-UHFFFAOYSA-N 2-[4-[1-[2-(oxan-4-yl)ethyl]-2h-pyrazin-5-yl]phenyl]propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1C(N=CC1)=CN1CCC1CCOCC1 YLWPCUTVHSWTDT-UHFFFAOYSA-N 0.000 claims description 4
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
• 125000003963 dichloro group Chemical group Cl* 0.000 claims description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical group C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 claims description 4
• 239000011230 binding agent Substances 0.000 claims description 3
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
• JXKZMTFKUWWBQF-QGZVFWFLSA-N (2R)-2-(cyclohexylmethyl)-5-[4-(1H-1,2,4-triazol-5-yl)phenyl]-1,2-dihydropyrazine Chemical compound N1N=CN=C1C1=CC=C(C=C1)C1=CN[C@@H](C=N1)CC1CCCCC1 JXKZMTFKUWWBQF-QGZVFWFLSA-N 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• VQTIKTKQDPEAQY-UHFFFAOYSA-N 1-(2-methoxyethyl)-5-[4-(1H-1,2,4-triazol-5-yl)phenyl]-2H-pyrazine Chemical compound N=1N=C(NC=1)C1=CC=C(C=C1)C1=CN(CC=N1)CCOC VQTIKTKQDPEAQY-UHFFFAOYSA-N 0.000 claims description 2
• KGVOUTZGWDAHLQ-UHFFFAOYSA-N 1-(2-methoxyethyl)-5-[4-methyl-6-(1H-1,2,4-triazol-5-yl)pyridin-3-yl]-2H-pyrazine Chemical compound COCCN1CC=NC(=C1)C=1C=NC(=CC=1C)C1=NNC=N1 KGVOUTZGWDAHLQ-UHFFFAOYSA-N 0.000 claims description 2
• BXJMVOVPRNUDQQ-UHFFFAOYSA-N 1-[2-(oxan-4-yl)ethyl]-5-[3-(1H-1,2,4-triazol-5-yl)phenyl]-2H-pyrazine Chemical compound N1N=CN=C1C=1C=C(C=CC=1)C1=CN(CC=N1)CCC1CCOCC1 BXJMVOVPRNUDQQ-UHFFFAOYSA-N 0.000 claims description 2
• ZEMIOTKVMONDJV-UHFFFAOYSA-N 1-ethyl-5-[5-fluoro-2-methyl-4-(1H-1,2,4-triazol-5-yl)phenyl]-2H-pyrazine Chemical compound C(C)N1CC=NC(=C1)C1=C(C=C(C(=C1)F)C1=NNC=N1)C ZEMIOTKVMONDJV-UHFFFAOYSA-N 0.000 claims description 2
• KBPYENLSMMCPMH-CYBMUJFWSA-N 2-[5-[1-[(3R)-oxolan-3-yl]-2H-pyrazin-5-yl]pyridin-2-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=C(C=N1)C1=CN(CC=N1)[C@@H]1CCOC1 KBPYENLSMMCPMH-CYBMUJFWSA-N 0.000 claims description 2
• TYAMMNKVQSFFRX-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-(2-methylpropyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC(C)C)CC(=O)NC2=NC=C1C1=CC=C(C(C)(C)O)N=C1 TYAMMNKVQSFFRX-UHFFFAOYSA-N 0.000 claims description 2
• CBIIYNCVOYUQDQ-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-8-(3-methoxypropyl)-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCCOC)CC(=O)NC2=NC=C1C1=CC=C(C(C)(C)O)N=C1 CBIIYNCVOYUQDQ-UHFFFAOYSA-N 0.000 claims description 2
• GDXIINGDVFFEAX-UHFFFAOYSA-N 2-[6-methyl-5-[1-(oxan-4-ylmethyl)-2H-pyrazin-5-yl]pyridin-2-yl]propan-2-ol Chemical compound OC(C)(C)C1=CC=C(C(=N1)C)C1=CN(CC=N1)CC1CCOCC1 GDXIINGDVFFEAX-UHFFFAOYSA-N 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• JZOPHJLRUKZARE-UHFFFAOYSA-N 2-methyl-5-[2-methyl-4-(1H-1,2,4-triazol-5-yl)phenyl]-1-[2-(oxan-4-yl)ethyl]-2H-pyrazine Chemical compound CC1C=NC(=CN1CCC1CCOCC1)C1=C(C=C(C=C1)C1=NN=CN1)C JZOPHJLRUKZARE-UHFFFAOYSA-N 0.000 claims description 2
• PYIOCXUJMVMACJ-UHFFFAOYSA-N 3-[1-[2-(oxan-4-yl)ethyl]-2H-pyrazin-5-yl]-1H-pyrrolo[2,3-b]pyridine Chemical compound N1C=C(C=2C1=NC=CC=2)C1=CN(CC=N1)CCC1CCOCC1 PYIOCXUJMVMACJ-UHFFFAOYSA-N 0.000 claims description 2
• XSQAJVDTZWOBMX-UHFFFAOYSA-N 3-[6-(2-hydroxypropan-2-yl)pyridin-3-yl]-5-(2-methoxyethyl)-7,8-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CCOC)C(=O)CNC2=NC=C1C1=CC=C(C(C)(C)O)N=C1 XSQAJVDTZWOBMX-UHFFFAOYSA-N 0.000 claims description 2
• AIOUQYUFHADEHR-UHFFFAOYSA-N 3-methylpyridine-2-carboxamide Chemical compound CC1=CC=CN=C1C(N)=O AIOUQYUFHADEHR-UHFFFAOYSA-N 0.000 claims description 2
• UTBZNVDKNOTYRQ-UHFFFAOYSA-N 5-[2-methyl-4-(1H-1,2,4-triazol-5-yl)phenyl]-1-[2-(oxan-4-yl)ethyl]-2H-pyrazine Chemical compound CC1=C(C=CC(=C1)C1=NN=CN1)C1=CN(CC=N1)CCC1CCOCC1 UTBZNVDKNOTYRQ-UHFFFAOYSA-N 0.000 claims description 2
• QVJDYGVKEZGOLX-UHFFFAOYSA-N 5-[3-fluoro-2-methyl-4-(1H-1,2,4-triazol-5-yl)phenyl]-1-[2-(oxan-4-yl)ethyl]-2H-pyrazine Chemical compound CC1=C(C=CC(C2=NN=CN2)=C1F)C1=CN(CCC2CCOCC2)CC=N1 QVJDYGVKEZGOLX-UHFFFAOYSA-N 0.000 claims description 2
• OKISZOGYEWHHLJ-UHFFFAOYSA-N 5-[5-fluoro-2-methyl-4-(1H-1,2,4-triazol-5-yl)phenyl]-1-(2-methoxyethyl)-2H-pyrazine Chemical compound FC=1C(=CC(=C(C=1)C1=CN(CC=N1)CCOC)C)C1=NNC=N1 OKISZOGYEWHHLJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 2
• ZSMPGGSXRQZDSI-UHFFFAOYSA-N 8-ethyl-2-[4-(1h-1,2,4-triazol-5-yl)phenyl]-5,7-dihydropyrazino[2,3-b]pyrazin-6-one Chemical compound N1=C2N(CC)CC(=O)NC2=NC=C1C(C=C1)=CC=C1C1=NN=CN1 ZSMPGGSXRQZDSI-UHFFFAOYSA-N 0.000 claims description 2
• ZHGNHOOVYPHPNJ-UHFFFAOYSA-N Amigdalin Chemical compound FC(F)(F)C(=O)OCC1OC(OCC2OC(OC(C#N)C3=CC=CC=C3)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C2OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C1OC(=O)C(F)(F)F ZHGNHOOVYPHPNJ-UHFFFAOYSA-N 0.000 claims description 2
• MYBXLGOKGJHUTF-OTVXOJSOSA-N N1N=C(N=C1)C1=CC=C(C=N1)C1=CN(CC=N1)C[C@@H]1CC[C@@H](CC1)O Chemical compound N1N=C(N=C1)C1=CC=C(C=N1)C1=CN(CC=N1)C[C@@H]1CC[C@@H](CC1)O MYBXLGOKGJHUTF-OTVXOJSOSA-N 0.000 claims description 2
• GWYCFNCAHFSQSF-WKILWMFISA-N OC(C)(C)C1=CC=C(C(=N1)C)C1=CN(CC=N1)[C@@H]1CC[C@H](CC1)OC Chemical compound OC(C)(C)C1=CC=C(C(=N1)C)C1=CN(CC=N1)[C@@H]1CC[C@H](CC1)OC GWYCFNCAHFSQSF-WKILWMFISA-N 0.000 claims description 2
• UPBMCMHHAALSFQ-SHTZXODSSA-N O[C@@H]1CC[C@H](CC1)N1CC=NC(=C1)C=1C=NC(=CC=1)C(C)(C)O Chemical compound O[C@@H]1CC[C@H](CC1)N1CC=NC(=C1)C=1C=NC(=CC=1)C(C)(C)O UPBMCMHHAALSFQ-SHTZXODSSA-N 0.000 claims description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims description 2
• 229910052700 potassium Inorganic materials 0.000 claims description 2
• 239000011591 potassium Substances 0.000 claims description 2
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 2
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
• OQJVXNHMUWQQEW-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine Chemical compound C1CNC=CN1 OQJVXNHMUWQQEW-UHFFFAOYSA-N 0.000 claims 1
• QZXAXWMKZXNBOG-OAHLLOKOSA-N 1-[[(2R)-oxolan-2-yl]methyl]-5-[4-(1H-1,2,4-triazol-5-yl)phenyl]-2H-pyrazine Chemical compound N=1N=C(NC=1)C1=CC=C(C=C1)C1=CN(CC=N1)C[C@@H]1OCCC1 QZXAXWMKZXNBOG-OAHLLOKOSA-N 0.000 claims 1
• QUPBLYKHWIOMGL-UHFFFAOYSA-N 1-ethyl-5-[6-(1h-1,2,4-triazol-5-yl)pyridin-3-yl]-2h-pyrazine Chemical compound CCN1CC=NC(C=2C=NC(=CC=2)C=2NN=CN=2)=C1 QUPBLYKHWIOMGL-UHFFFAOYSA-N 0.000 claims 1
• SUFNSMWCIULSNK-UHFFFAOYSA-N 1-propan-2-yl-5-[6-(1H-1,2,4-triazol-5-yl)pyridin-3-yl]-2H-pyrazine Chemical compound N1N=C(N=C1)C1=CC=C(C=N1)C1=CN(CC=N1)C(C)C SUFNSMWCIULSNK-UHFFFAOYSA-N 0.000 claims 1
• SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims 1
• PJTQQEBZJCYPSX-UHFFFAOYSA-N 2-[4-[1-(oxan-4-ylmethyl)-2H-pyrazin-5-yl]phenyl]propan-2-ol Chemical compound OC(C)(C)C1=CC=C(C=C1)C1=CN(CC=N1)CC1CCOCC1 PJTQQEBZJCYPSX-UHFFFAOYSA-N 0.000 claims 1
• CJTBBKVROHUZHW-UHFFFAOYSA-N 2-[4-methyl-5-[1-(oxan-4-ylmethyl)-2H-pyrazin-5-yl]pyridin-2-yl]propan-2-ol Chemical compound CC1=C(C=NC(=C1)C(C)(C)O)C1=CN(CC2CCOCC2)CC=N1 CJTBBKVROHUZHW-UHFFFAOYSA-N 0.000 claims 1
• JAIBITQUJGCXDB-UHFFFAOYSA-N 2-[5-[1-(2-morpholin-4-ylethyl)-2H-pyrazin-5-yl]pyridin-2-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=C(C=N1)C1=CN(CCN2CCOCC2)CC=N1 JAIBITQUJGCXDB-UHFFFAOYSA-N 0.000 claims 1
• VVTOXAWPJURYJC-UHFFFAOYSA-N 2-[5-[1-(cyclopentylmethyl)-2H-pyrazin-5-yl]pyridin-2-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=C(C=N1)C1=CN(CC2CCCC2)CC=N1 VVTOXAWPJURYJC-UHFFFAOYSA-N 0.000 claims 1
• FHYHXDVRIKIWDD-UHFFFAOYSA-N 2-[5-[1-[2-(oxan-3-yl)ethyl]-2H-pyrazin-5-yl]pyridin-2-yl]propan-2-ol Chemical compound OC(C)(C)C1=CC=C(C=N1)C1=CN(CC=N1)CCC1COCCC1 FHYHXDVRIKIWDD-UHFFFAOYSA-N 0.000 claims 1
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