IL99913A

IL99913A - 2-סכרינילמתיל אריל קרבוקסילטים, הכנתם ותכשירי רוקחות המכילים אותם

2-סכרינילמתיל אריל קרבוקסילטים, הכנתם ותכשירי רוקחות המכילים אותם

Info

Publication number: IL99913A
Authority: IL; Israel
Prior art keywords: alkyl; alkoxy; alkylene; isopropyl; mol
Prior art date: 1990-11-01

Application number

IL9991391A

Other languages

English (en)

Other versions

IL99913A0 (en

Original Assignee

Sterling Winthrop Inc

Priority date

1990-11-01

Filing date

1991-10-31

Publication date

1996-11-14

1991-10-31 Application filed by Sterling Winthrop Inc filed Critical Sterling Winthrop Inc

1991-10-31 Priority to IL11477391A priority Critical patent/IL114773A/he

1992-08-18 Publication of IL99913A0 publication Critical patent/IL99913A0/xx

1996-11-14 Publication of IL99913A publication Critical patent/IL99913A/he

Links

-1 2-Saccharinylmethyl aryl carboxylates Chemical class 0.000 title claims description 171
238000002360 preparation method Methods 0.000 title description 106
239000008194 pharmaceutical composition Substances 0.000 title description 2
239000000203 mixture Substances 0.000 claims description 117
238000000034 method Methods 0.000 claims description 83
229940081974 saccharin Drugs 0.000 claims description 80
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 80
235000019204 saccharin Nutrition 0.000 claims description 72
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 69
RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 65
150000001875 compounds Chemical class 0.000 claims description 64
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 54
150000003839 salts Chemical class 0.000 claims description 54
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
239000002253 acid Substances 0.000 claims description 45
239000001257 hydrogen Substances 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 42
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
125000002947 alkylene group Chemical group 0.000 claims description 36
229910052783 alkali metal Inorganic materials 0.000 claims description 29
229910052757 nitrogen Inorganic materials 0.000 claims description 29
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 28
150000002367 halogens Chemical class 0.000 claims description 27
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 24
239000002585 base Substances 0.000 claims description 24
238000010438 heat treatment Methods 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
150000002431 hydrogen Chemical class 0.000 claims description 20
229920006395 saturated elastomer Polymers 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
150000007513 acids Chemical class 0.000 claims description 15
230000008569 process Effects 0.000 claims description 14
102000035195 Peptidases Human genes 0.000 claims description 13
108091005804 Peptidases Proteins 0.000 claims description 13
150000001340 alkali metals Chemical class 0.000 claims description 13
230000002401 inhibitory effect Effects 0.000 claims description 13
229910021529 ammonia Inorganic materials 0.000 claims description 12
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 12
125000001624 naphthyl group Chemical group 0.000 claims description 12
208000015122 neurodegenerative disease Diseases 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 10
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 9
MRUDNSFOFOQZDA-UHFFFAOYSA-N 2,6-dichlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC=C1Cl MRUDNSFOFOQZDA-UHFFFAOYSA-N 0.000 claims description 8
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 8
150000001241 acetals Chemical class 0.000 claims description 8
DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
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 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
229930040373 Paraformaldehyde Natural products 0.000 claims description 7
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 7
125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
229920002866 paraformaldehyde Polymers 0.000 claims description 7
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
229910052744 lithium Inorganic materials 0.000 claims description 6
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 6
RRURGOPYONTFSU-UHFFFAOYSA-N (6-hydroxy-1,1,3-trioxo-4-propan-2-yl-1,2-benzothiazol-2-yl)methyl 2,6-dichlorobenzoate Chemical compound CC(C)C1=CC(O)=CC(S2(=O)=O)=C1C(=O)N2COC(=O)C1=C(Cl)C=CC=C1Cl RRURGOPYONTFSU-UHFFFAOYSA-N 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000005046 Chlorosilane Substances 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
239000011260 aqueous acid Substances 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000002841 Lewis acid Substances 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
150000007517 lewis acids Chemical class 0.000 claims description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
229910052716 thallium Inorganic materials 0.000 claims description 2
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
241000282320 Panthera leo Species 0.000 claims 4
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 4
125000005518 carboxamido group Chemical group 0.000 claims 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
150000007514 bases Chemical class 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
239000001301 oxygen Substances 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
239000011593 sulfur Substances 0.000 claims 2
229910052717 sulfur Inorganic materials 0.000 claims 2
ZXDOSVYEJCJHJX-UHFFFAOYSA-N (1,1,3-trioxo-4-propan-2-yl-6-propan-2-yloxy-1,2-benzothiazol-2-yl)methyl 2,6-dichlorobenzoate Chemical compound CC(C)C1=CC(OC(C)C)=CC(S2(=O)=O)=C1C(=O)N2COC(=O)C1=C(Cl)C=CC=C1Cl ZXDOSVYEJCJHJX-UHFFFAOYSA-N 0.000 claims 1
PJZFNQHNGCCQFF-UHFFFAOYSA-N (5,6-dimethoxy-1,1,3-trioxo-4-propan-2-yl-1,2-benzothiazol-2-yl)methyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OCN3C(=O)C4=C(S3(=O)=O)C=C(C(=C4C(C)C)OC)OC)=CC=CC2=C1 PJZFNQHNGCCQFF-UHFFFAOYSA-N 0.000 claims 1
DJRCXWFCZRAPCO-UHFFFAOYSA-N (6-methoxy-1,1,3-trioxo-4-propan-2-yl-1,2-benzothiazol-2-yl)methyl 2,6-dichloro-3-hydroxybenzoate Chemical compound CC(C)C1=CC(OC)=CC(S2(=O)=O)=C1C(=O)N2COC(=O)C1=C(Cl)C=CC(O)=C1Cl DJRCXWFCZRAPCO-UHFFFAOYSA-N 0.000 claims 1
ZNRMNTBTLWKEQJ-UHFFFAOYSA-N (6-methoxy-1,1,3-trioxo-4-propan-2-yl-1,2-benzothiazol-2-yl)methyl 2,6-dimethylbenzoate Chemical compound CC(C)C1=CC(OC)=CC(S2(=O)=O)=C1C(=O)N2COC(=O)C1=C(C)C=CC=C1C ZNRMNTBTLWKEQJ-UHFFFAOYSA-N 0.000 claims 1
CTZDCUSZXMZFNM-UHFFFAOYSA-N 2-methyl-2h-1,3-oxazine Chemical compound CC1OC=CC=N1 CTZDCUSZXMZFNM-UHFFFAOYSA-N 0.000 claims 1
ANZVLSXRDUMVNT-UHFFFAOYSA-N CC(C)C1=CC=2OCOC=2C(S2(=O)=O)=C1C(=O)N2COC(=O)C1=C(Cl)C=CC=C1Cl Chemical compound CC(C)C1=CC=2OCOC=2C(S2(=O)=O)=C1C(=O)N2COC(=O)C1=C(Cl)C=CC=C1Cl ANZVLSXRDUMVNT-UHFFFAOYSA-N 0.000 claims 1
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
FISPTDASSBWZML-UHFFFAOYSA-N [6-(2,3-dimethoxypropoxy)-1,1,3-trioxo-4-propan-2-yl-1,2-benzothiazol-2-yl]methyl 2,6-dichlorobenzoate Chemical compound CC(C)C1=CC(OCC(COC)OC)=CC(S2(=O)=O)=C1C(=O)N2COC(=O)C1=C(Cl)C=CC=C1Cl FISPTDASSBWZML-UHFFFAOYSA-N 0.000 claims 1
UGIABZRUEMNNRV-UHFFFAOYSA-N [6-(2-morpholin-4-ylethoxy)-1,1,3-trioxo-4-propan-2-yl-1,2-benzothiazol-2-yl]methyl 2,6-dichlorobenzoate Chemical compound C=1C(S(N(COC(=O)C=2C(=CC=CC=2Cl)Cl)C2=O)(=O)=O)=C2C(C(C)C)=CC=1OCCN1CCOCC1 UGIABZRUEMNNRV-UHFFFAOYSA-N 0.000 claims 1
ULAAUAXWEYLOCB-UHFFFAOYSA-N [6-[2-(2-methoxyethoxy)ethoxy]-1,1,3-trioxo-4-propan-2-yl-1,2-benzothiazol-2-yl]methyl 2,6-dichlorobenzoate Chemical compound CC(C)C1=CC(OCCOCCOC)=CC(S2(=O)=O)=C1C(=O)N2COC(=O)C1=C(Cl)C=CC=C1Cl ULAAUAXWEYLOCB-UHFFFAOYSA-N 0.000 claims 1
125000000068 chlorophenyl group Chemical group 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 188
239000000243 solution Substances 0.000 description 151
238000006243 chemical reaction Methods 0.000 description 139
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 135
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 131
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 120
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 119
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 93
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 88
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
229910001868 water Inorganic materials 0.000 description 77
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
235000019439 ethyl acetate Nutrition 0.000 description 46
239000007787 solid Substances 0.000 description 44
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
239000011541 reaction mixture Substances 0.000 description 38
229960000583 acetic acid Drugs 0.000 description 37
239000000741 silica gel Substances 0.000 description 37
229910002027 silica gel Inorganic materials 0.000 description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
239000000047 product Substances 0.000 description 36
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 35
239000002904 solvent Substances 0.000 description 32
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 30
239000012267 brine Substances 0.000 description 28
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 28
238000010992 reflux Methods 0.000 description 25
238000003756 stirring Methods 0.000 description 25
239000003921 oil Substances 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
VVPUIKNICYCXJZ-UHFFFAOYSA-N 4-iodobutyl benzoate Chemical compound ICCCCOC(=O)C1=CC=CC=C1 VVPUIKNICYCXJZ-UHFFFAOYSA-N 0.000 description 23
239000012362 glacial acetic acid Substances 0.000 description 23
229940044609 sulfur dioxide Drugs 0.000 description 23
238000001914 filtration Methods 0.000 description 22
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 20
239000000706 filtrate Substances 0.000 description 19
229910000027 potassium carbonate Inorganic materials 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
238000003818 flash chromatography Methods 0.000 description 17
238000000746 purification Methods 0.000 description 17
150000007942 carboxylates Chemical class 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
239000000284 extract Substances 0.000 description 13
239000010410 layer Substances 0.000 description 13
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 12
229960004132 diethyl ether Drugs 0.000 description 12
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 12
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
102000004190 Enzymes Human genes 0.000 description 11
108090000790 Enzymes Proteins 0.000 description 11
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 11
235000011114 ammonium hydroxide Nutrition 0.000 description 11
229940088598 enzyme Drugs 0.000 description 11
229910003002 lithium salt Inorganic materials 0.000 description 11
159000000002 lithium salts Chemical class 0.000 description 11
235000011181 potassium carbonates Nutrition 0.000 description 11
230000002829 reductive effect Effects 0.000 description 11
ZTMWHBJKVKHBTO-UHFFFAOYSA-M sodium amino sulfate Chemical compound [Na+].NOS([O-])(=O)=O ZTMWHBJKVKHBTO-UHFFFAOYSA-M 0.000 description 11
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
239000005457 ice water Substances 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
150000003475 thallium Chemical class 0.000 description 9
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000006260 foam Substances 0.000 description 8
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YZUAOVCUGSBIPP-UHFFFAOYSA-N tert-butyl N-[1-([1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl]carbamate Chemical compound C1=CC=CN2C(C(NC(=O)OC(C)(C)C)C)=NN=C21 YZUAOVCUGSBIPP-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
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ZCPSWAFANXCCOT-UHFFFAOYSA-N trichloromethanesulfonyl chloride Chemical compound ClC(Cl)(Cl)S(Cl)(=O)=O ZCPSWAFANXCCOT-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
MFLLMKMFWIUACU-UHFFFAOYSA-N trifluoromethanethiol Chemical compound FC(F)(F)S MFLLMKMFWIUACU-UHFFFAOYSA-N 0.000 description 1
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125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000001665 trituration Methods 0.000 description 1
ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1