SA94140632A - مركبات 1 - أسيل بيبريدين - Google Patents

Info

Publication number

SA94140632A

SA94140632A SA94140632A SA94140632A SA94140632A SA 94140632 A SA94140632 A SA 94140632A SA 94140632 A SA94140632 A SA 94140632A SA 94140632 A SA94140632 A SA 94140632A SA 94140632 A SA94140632 A SA 94140632A

Authority

SA

Saudi Arabia

Prior art keywords

pyridineamine

benzyl

dimethylbenzoyl

methyl

ethyl

Prior art date

1991-08-12

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• -1 aralkanol Chemical group 0.000 claims abstract description 369
• 150000003839 salts Chemical class 0.000 claims abstract description 156
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 108
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 94
• 238000000034 method Methods 0.000 claims abstract description 81
• 230000008569 process Effects 0.000 claims abstract description 69
• 239000002253 acid Substances 0.000 claims abstract description 42
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
• 239000001257 hydrogen Substances 0.000 claims abstract description 39
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 35
• 229920002554 vinyl polymer Polymers 0.000 claims abstract description 32
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
• 150000001412 amines Chemical class 0.000 claims abstract description 15
• 125000003118 aryl group Chemical group 0.000 claims abstract description 13
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract description 10
• 238000011065 in-situ storage Methods 0.000 claims abstract description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims abstract description 3
• QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims abstract 2
• 102100024304 Protachykinin-1 Human genes 0.000 claims abstract 2
• 101800003906 Substance P Proteins 0.000 claims abstract 2
• 150000001875 compounds Chemical class 0.000 claims description 368
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 170
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 136
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 107
• 239000000203 mixture Substances 0.000 claims description 89
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 75
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 65
• 125000002947 alkylene group Chemical group 0.000 claims description 64
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 64
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 60
• 229910052736 halogen Inorganic materials 0.000 claims description 59
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
• 150000002367 halogens Chemical class 0.000 claims description 55
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 39
• 125000006286 dichlorobenzyl group Chemical group 0.000 claims description 35
• 230000002829 reductive effect Effects 0.000 claims description 34
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
• 239000005977 Ethylene Substances 0.000 claims description 33
• 125000005493 quinolyl group Chemical group 0.000 claims description 31
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 28
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 25
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 25
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 23
• 125000001589 carboacyl group Chemical group 0.000 claims description 22
• 150000007942 carboxylates Chemical class 0.000 claims description 18
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 16
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 16
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
• 239000000463 material Substances 0.000 claims description 13
• PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 claims description 13
• 125000001624 naphthyl group Chemical group 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 12
• 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 239000007858 starting material Substances 0.000 claims description 11
• 235000001014 amino acid Nutrition 0.000 claims description 10
• 239000004305 biphenyl Substances 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 229910052751 metal Inorganic materials 0.000 claims description 10
• 239000002184 metal Substances 0.000 claims description 10
• 230000009467 reduction Effects 0.000 claims description 10
• 150000001413 amino acids Chemical class 0.000 claims description 9
• 125000001041 indolyl group Chemical group 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 125000006003 dichloroethyl group Chemical group 0.000 claims description 8
• 239000000543 intermediate Substances 0.000 claims description 8
• 125000000405 phenylalanyl group Chemical group 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
• 125000003277 amino group Chemical group 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 125000004803 chlorobenzyl group Chemical group 0.000 claims description 6
• 150000003254 radicals Chemical class 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 238000005804 alkylation reaction Methods 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
• 241001465754 Metazoa Species 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 230000015572 biosynthetic process Effects 0.000 claims description 4
• 125000004188 dichlorophenyl group Chemical group 0.000 claims description 4
• 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
• 201000010099 disease Diseases 0.000 claims description 4
• 239000004615 ingredient Substances 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 4
• 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 238000003776 cleavage reaction Methods 0.000 claims description 3
• 125000003963 dichloro group Chemical group Cl* 0.000 claims description 3
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 230000000144 pharmacologic effect Effects 0.000 claims description 3
• 230000007017 scission Effects 0.000 claims description 3
• 125000001424 substituent group Chemical group 0.000 claims description 3
• 125000002252 acyl group Chemical group 0.000 claims description 2
• 235000008206 alpha-amino acids Nutrition 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 230000014509 gene expression Effects 0.000 claims description 2
• 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 2
• 150000003852 triazoles Chemical class 0.000 claims description 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 15
• 125000004663 dialkyl amino group Chemical group 0.000 claims 4
• 230000029936 alkylation Effects 0.000 claims 3
• 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
• 125000000547 substituted alkyl group Chemical group 0.000 claims 2
• 125000003107 substituted aryl group Chemical group 0.000 claims 2
• ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims 2
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
• 240000007124 Brassica oleracea Species 0.000 claims 1
• 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims 1
• 235000012905 Brassica oleracea var viridis Nutrition 0.000 claims 1
• 240000006162 Chenopodium quinoa Species 0.000 claims 1
• JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims 1
• 206010011732 Cyst Diseases 0.000 claims 1
• 240000006927 Foeniculum vulgare Species 0.000 claims 1
• 235000004204 Foeniculum vulgare Nutrition 0.000 claims 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
• 239000004472 Lysine Substances 0.000 claims 1
• 101000942305 Zea mays Cytokinin dehydrogenase 1 Proteins 0.000 claims 1
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
• 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 1
• 125000003943 azolyl group Chemical group 0.000 claims 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
• FDODVZVWGKVMBO-UHFFFAOYSA-N cyclohex-2-ene-1,4-diol Chemical compound OC1CCC(O)C=C1 FDODVZVWGKVMBO-UHFFFAOYSA-N 0.000 claims 1
• 208000031513 cyst Diseases 0.000 claims 1
• 125000001207 fluorophenyl group Chemical group 0.000 claims 1
• 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical class O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
• 125000005647 linker group Chemical group 0.000 claims 1
• 229960005181 morphine Drugs 0.000 claims 1
• 230000001681 protective effect Effects 0.000 claims 1
• WZCZNEGTXVXAAS-UHFFFAOYSA-N trifluoromethanol Chemical compound OC(F)(F)F WZCZNEGTXVXAAS-UHFFFAOYSA-N 0.000 claims 1
• 238000011144 upstream manufacturing Methods 0.000 claims 1
• 239000013543 active substance Substances 0.000 abstract description 7
• 150000001408 amides Chemical class 0.000 abstract description 3
• 230000036961 partial effect Effects 0.000 abstract description 2
• 230000001575 pathological effect Effects 0.000 abstract description 2
• HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical group CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
• 125000004404 heteroalkyl group Chemical group 0.000 abstract 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 571
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 525
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 255
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 179
• 229910021529 ammonia Inorganic materials 0.000 description 127
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 120
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 114
• 239000000243 solution Substances 0.000 description 104
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
• 239000006260 foam Substances 0.000 description 66
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
• 239000003921 oil Substances 0.000 description 64
• 235000019198 oils Nutrition 0.000 description 64
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 62
• 238000000434 field desorption mass spectrometry Methods 0.000 description 60
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
• 239000012141 concentrate Substances 0.000 description 47
• 239000012279 sodium borohydride Substances 0.000 description 45
• 229910000033 sodium borohydride Inorganic materials 0.000 description 45
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
• 150000007530 organic bases Chemical class 0.000 description 40
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
• 238000002844 melting Methods 0.000 description 36
• 230000008018 melting Effects 0.000 description 36
• 239000011541 reaction mixture Substances 0.000 description 35
• 229960001866 silicon dioxide Drugs 0.000 description 34
• 239000000741 silica gel Substances 0.000 description 32
• 229910002027 silica gel Inorganic materials 0.000 description 32
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 31
• 235000019341 magnesium sulphate Nutrition 0.000 description 31
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 29
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 25
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
• 239000002994 raw material Substances 0.000 description 23
• 239000011734 sodium Substances 0.000 description 23
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 21
• 239000010410 layer Substances 0.000 description 21
• 229910052938 sodium sulfate Inorganic materials 0.000 description 21
• 235000011152 sodium sulphate Nutrition 0.000 description 21
• 238000003756 stirring Methods 0.000 description 21
• 239000000460 chlorine Substances 0.000 description 20
• 238000004587 chromatography analysis Methods 0.000 description 20
• 239000000047 product Substances 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
• 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 18
• 235000011114 ammonium hydroxide Nutrition 0.000 description 18
• 229910052708 sodium Inorganic materials 0.000 description 18
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 17
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 17
• 239000000725 suspension Substances 0.000 description 17
• 239000002585 base Substances 0.000 description 16
• 239000012458 free base Substances 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 15
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-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 14
• 239000012267 brine Substances 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• 239000013078 crystal Substances 0.000 description 13
• 150000002148 esters Chemical class 0.000 description 13
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• 239000003054 catalyst Substances 0.000 description 10
• 229910052801 chlorine Inorganic materials 0.000 description 10
• 125000004043 oxo group Chemical group O=* 0.000 description 10
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 10
• 239000000126 substance Substances 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 9
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• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
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