CS36192A3 - Nitrogen hetero cycles, process of their preparation and pharmaceuticalcompositions containing said hetero cycles - Google Patents

Info

Publication number

CS36192A3

CS36192A3 CS92361A CS36192A CS36192A3 CS 36192 A3 CS36192 A3 CS 36192A3 CS 92361 A CS92361 A CS 92361A CS 36192 A CS36192 A CS 36192A CS 36192 A3 CS36192 A3 CS 36192A3

Authority

CS

Czechoslovakia

Prior art keywords

group

carbon atoms

alkyl

formula

atom

Prior art date

1991-02-11

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 46
• 229910052757 nitrogen Inorganic materials 0.000 title claims description 25
• 238000002360 preparation method Methods 0.000 title claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 title claims description 20
• 230000008569 process Effects 0.000 title claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
• -1 cycloalkyl radical Chemical class 0.000 claims description 268
• 125000004432 carbon atom Chemical group C* 0.000 claims description 201
• 150000001875 compounds Chemical class 0.000 claims description 181
• 125000001424 substituent group Chemical group 0.000 claims description 113
• 125000000217 alkyl group Chemical group 0.000 claims description 100
• 239000000203 mixture Substances 0.000 claims description 79
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 59
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
• 238000006243 chemical reaction Methods 0.000 claims description 47
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
• 125000003545 alkoxy group Chemical group 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 38
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 34
• 239000007858 starting material Substances 0.000 claims description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 26
• 229910052783 alkali metal Inorganic materials 0.000 claims description 25
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 25
• 125000005843 halogen group Chemical group 0.000 claims description 25
• 239000002585 base Substances 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 239000000460 chlorine Substances 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 231100000252 nontoxic Toxicity 0.000 claims description 20
• 230000003000 nontoxic effect Effects 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
• 150000001721 carbon Chemical group 0.000 claims description 18
• 125000001153 fluoro group Chemical group F* 0.000 claims description 18
• 150000002367 halogens Chemical group 0.000 claims description 18
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 239000002253 acid Substances 0.000 claims description 16
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 16
• 150000003254 radicals Chemical class 0.000 claims description 16
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
• 125000003282 alkyl amino group Chemical group 0.000 claims description 13
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 13
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
• 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 11
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 229910052740 iodine Inorganic materials 0.000 claims description 11
• 150000002825 nitriles Chemical class 0.000 claims description 11
• 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 10
• 125000002252 acyl group Chemical group 0.000 claims description 10
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 10
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 125000003277 amino group Chemical group 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
• 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 7
• 150000001204 N-oxides Chemical class 0.000 claims description 7
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
• 239000003054 catalyst Substances 0.000 claims description 7
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 7
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 7
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 6
• 150000001340 alkali metals Chemical class 0.000 claims description 6
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 6
• 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims description 6
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
• 150000007530 organic bases Chemical class 0.000 claims description 6
• 125000006239 protecting group Chemical group 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
• 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 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 229940031826 phenolate Drugs 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 4
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 125000004423 acyloxy group Chemical group 0.000 claims description 4
• 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
• 125000004450 alkenylene group Chemical group 0.000 claims description 4
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
• 150000003927 aminopyridines Chemical class 0.000 claims description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 150000001540 azides Chemical class 0.000 claims description 4
• 125000006309 butyl amino group Chemical group 0.000 claims description 4
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 230000002950 deficient Effects 0.000 claims description 4
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
• SDVKFPLYSRNCLR-UHFFFAOYSA-N 2-(pyridin-4-ylmethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CC1=CC=NC=C1 SDVKFPLYSRNCLR-UHFFFAOYSA-N 0.000 claims description 3
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 3
• 150000003973 alkyl amines Chemical class 0.000 claims description 3
• 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
• 150000002440 hydroxy compounds Chemical class 0.000 claims description 3
• BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 229910052751 metal Inorganic materials 0.000 claims description 3
• 239000002184 metal Substances 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
• 125000002071 phenylalkoxy group Chemical group 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000006413 ring segment Chemical group 0.000 claims description 3
• 229940124530 sulfonamide Drugs 0.000 claims description 3
• 150000003456 sulfonamides Chemical class 0.000 claims description 3
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
• ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 claims description 2
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 2
• ZJJLFCGQWMKQPM-UHFFFAOYSA-N 4-[(pyridin-1-ium-4-ylamino)methyl]benzoate Chemical compound C1=CC(C(=O)O)=CC=C1CNC1=CC=NC=C1 ZJJLFCGQWMKQPM-UHFFFAOYSA-N 0.000 claims description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 2
• 230000002152 alkylating effect Effects 0.000 claims description 2
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000003368 amide group Chemical group 0.000 claims description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
• 150000003863 ammonium salts Chemical class 0.000 claims description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
• 238000007796 conventional method Methods 0.000 claims description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
• 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
• 125000005936 piperidyl group Chemical group 0.000 claims description 2
• 150000003222 pyridines Chemical class 0.000 claims description 2
• 239000011593 sulfur Chemical group 0.000 claims description 2
• 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 2
• 230000000295 complement effect Effects 0.000 claims 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
• FLYHLGAYIIUJBU-UHFFFAOYSA-N 3,3,3-trifluoropropyl hypofluorite Chemical compound FOCCC(F)(F)F FLYHLGAYIIUJBU-UHFFFAOYSA-N 0.000 claims 1
• HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 claims 1
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
• 238000010306 acid treatment Methods 0.000 claims 1
• 150000001336 alkenes Chemical group 0.000 claims 1
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
• KHBQMWCZKVMBLN-IDEBNGHGSA-N benzenesulfonamide Chemical group NS(=O)(=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 KHBQMWCZKVMBLN-IDEBNGHGSA-N 0.000 claims 1
• JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims 1
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
• 150000002500 ions Chemical class 0.000 claims 1
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• 125000005968 oxazolinyl group Chemical group 0.000 claims 1
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
• QLNJFJADRCOGBJ-LBPDFUHNSA-N propanamide Chemical group CC[13C](N)=O QLNJFJADRCOGBJ-LBPDFUHNSA-N 0.000 claims 1
• 239000001294 propane Substances 0.000 claims 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 153
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
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