BE509212A

BE509212A -

Info

Publication number: BE509212A
Authority: BE; Belgium
Prior art keywords: isonicotinyl; methanol; hydrazine; mixture; isonicotinic acid
Prior art date

Application number

Other languages

English (en)

French (fr)

Publication of BE509212A publication Critical patent/BE509212A/fr

Links

238000000034 method Methods 0.000 claims description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 12
238000005984 hydrogenation reaction Methods 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 3
150000007857 hydrazones Chemical class 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 2
HBWAYDBIHKCBLG-UHFFFAOYSA-N 1-propan-2-yl-2-(pyridin-4-ylmethyl)hydrazine Chemical compound CC(C)NNCC1=CC=NC=C1 HBWAYDBIHKCBLG-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
239000000203 mixture Substances 0.000 description 19
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
150000001875 compounds Chemical class 0.000 description 12
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
-1 aliphatic ketones Chemical class 0.000 description 7
239000013078 crystal Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 4
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
150000001728 carbonyl compounds Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
239000008096 xylene Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
XWWUOLXCZZCUFH-UHFFFAOYSA-N N-(propan-2-ylideneamino)-1-pyridin-4-ylmethanamine Chemical compound C(C1=CC=NC=C1)NN=C(C)C XWWUOLXCZZCUFH-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
125000001118 alkylidene group Chemical group 0.000 description 2
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
MDRCUUFMSBITTA-UHFFFAOYSA-N 1-(2-methylpropyl)-2-(pyridin-4-ylmethyl)hydrazine Chemical compound CC(C)CNNCC1=CC=NC=C1 MDRCUUFMSBITTA-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical class CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical class CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WYTUHKLKMLKCRL-UHFFFAOYSA-N C(C1=CC=NC=C1)NN=C(CCCCCC)C Chemical compound C(C1=CC=NC=C1)NN=C(CCCCCC)C WYTUHKLKMLKCRL-UHFFFAOYSA-N 0.000 description 1
LRJJLXIFXPLHNP-UHFFFAOYSA-N C(C1=CC=NC=C1)NNCCCC Chemical compound C(C1=CC=NC=C1)NNCCCC LRJJLXIFXPLHNP-UHFFFAOYSA-N 0.000 description 1
KFFDYWKVPLSMSJ-UHFFFAOYSA-N N-(cyclohexylideneamino)-1-pyridin-4-ylmethanamine Chemical compound C(C1=CC=NC=C1)NN=C1CCCCC1 KFFDYWKVPLSMSJ-UHFFFAOYSA-N 0.000 description 1
DWCBDNDOAKODRP-UHFFFAOYSA-N N-(furan-2-ylmethylideneamino)-1-pyridin-4-ylmethanamine Chemical compound C(C1=CC=NC=C1)NN=CC1=CC=CO1 DWCBDNDOAKODRP-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
FOCKSELMWYAKOC-UHFFFAOYSA-N n-(ethylideneamino)-1-pyridin-4-ylmethanamine Chemical compound CC=NNCC1=CC=NC=C1 FOCKSELMWYAKOC-UHFFFAOYSA-N 0.000 description 1
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical class CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical class CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1