JP2017502963A - 5−フルオロ−4−イミノ−3−(アルキル/置換アルキル)−1−(アリールスルホニル)−3,4−ジヒドロピリミジン−2(1h)−オンおよびそれらの調製方法 - Google Patents
5−フルオロ−4−イミノ−3−(アルキル/置換アルキル)−1−(アリールスルホニル)−3,4−ジヒドロピリミジン−2(1h)−オンおよびそれらの調製方法 Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 47
- 125000000217 alkyl group Chemical group 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 title abstract description 5
- 125000000547 substituted alkyl group Chemical group 0.000 title abstract description 5
- 239000003513 alkali Substances 0.000 claims abstract description 18
- 239000002168 alkylating agent Substances 0.000 claims abstract description 16
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 42
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 24
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 16
- -1 benzyl halides Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- 239000011734 sodium Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 6
- FDYDGPMTLJGGMJ-UHFFFAOYSA-N 4-amino-1-(benzenesulfonyl)-5-fluoropyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1S(=O)(=O)C1=CC=CC=C1 FDYDGPMTLJGGMJ-UHFFFAOYSA-N 0.000 description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KVUHRPLZWABERU-UHFFFAOYSA-N 5-fluoro-4-imino-3-methyl-1-(4-methylphenyl)sulfonylpyrimidin-2-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(=O)N(C)C(=N)C(F)=C1 KVUHRPLZWABERU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- IGEAUAWXDNMZMF-UHFFFAOYSA-N 4-amino-5-fluoro-1-(4-methylphenyl)sulfonylpyrimidin-2-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(=O)N=C(N)C(F)=C1 IGEAUAWXDNMZMF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 1
- 229960004413 flucytosine Drugs 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 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 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C07D333/10—Thiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Abstract
Description
本出願は、各開示が参照により本明細書に特に組み込まれる2013年12月31日出願の米国特許仮出願第61/922,582号および第61/922,572号の各々の利益を主張する。
本明細書において、5−フルオロ−4−イミノ−3−(アルキル/置換アルキル)−1−(アリールスルホニル)−3,4−ジヒドロピリミジン−2(1H)−オンおよびそれらの調製方法が提供される。
米国特許出願第13/090,616号、米国特許公開第2011/0263627号には、とりわけあるN3置換−N1−スルホニル−5−フルオロピリミジノン化合物およびそれらの防カビ剤としての使用が記載されている。この出願の開示は、参照により本明細書に特に組み込まれる。この特許には、N3置換−N1−スルホニル−5−フルオロピリミジノン化合物を生成させる種々の経路が記載されている。N3置換−N1−スルホニル−5−フルオロピリミジノン防カビ剤および関連化合物を調製、単離、および精製するためのより直接的および効率的な方法を、例えば、試薬および/または化学的中間体の使用ならびに改善された時間およびコスト効率を提供する単離および精製技法により提供することは有益であろう。
R2は、
の化合物を調製するための方法であって、式IIの化合物を、塩基、例えば、アルカリ炭酸塩、例えば、炭酸ナトリウム、炭酸カリウム、炭酸セシウムおよび炭酸リチウム(それぞれ、Na2CO3、K2CO3、Cs2CO3およびLi2CO3)またはアルカリアルコキシド、例えば、カリウムtert−ブトキシド(KOtBu)およびアルキル化剤、例えば、式R2−X(式中、R2は前に定義されたものであり、Xはハロゲン、例えば、ヨウ素、臭素、および塩素である)のハロゲン化アルキルと、極性溶媒、例えば、N,N−ジメチルホルムアミド(DMF)、ジメチルスルホキシド(DMSO)、ジメチルアセトアミド(DMA)、N−メチルピロリドン(NMP)、アセトニトリル(CH3CN)などの中で、約0.1モル/L(molar)(M)から約3Mの濃度で接触させることを含む、方法が本明細書中で提供される。幾つかの実施形態では、式IIの化合物と塩基とのモル比は、約3:1から約1:1であり、式IIの化合物とアルキル化剤とのモル比は、約1:1から約3:1である。他の実施形態では、式IIの化合物と塩基とのモル比および式IIの化合物とアルキル化剤とのモル比は、それぞれ約2:1および1:3が使用される。幾つかの実施形態において、反応は−78℃と90℃の間の温度で実施され、他の実施形態では、反応は22℃と60℃の間で実施される。
R2は
実施例1〜2に示した5−フルオロ−4−イミノ−3−(アルキル/置換アルキル)−1−(アリールスルホニル)−3,4−ジヒドロ−ピリミジン−2(1H)−オン。
本発明は、以下の態様を包含し得る。
[1]
式IIIの化合物を製造する方法であって、
式II
式III
を含み、
R 1 は、
R 2 は、
[2]
前記接触させるステップが22℃と60℃の間で実施される、上記[1]に記載の方法。
[3]
前記接触させるステップが、DMF、DMSO、DMA、NMP、およびCH 3 CNからなる群から選択される溶媒をさらに含む、上記[1]に記載の方法。
[4]
前記炭酸アルカリが、Na 2 CO 3 、K 2 CO 3 、Cs 2 CO 3 、およびLi 2 CO 3 からなる群から選択される、上記[1]に記載の方法。
[5]
前記アルキル化剤が、ハロゲン化アルキルおよびハロゲン化ベンジルからなる群から選択される、上記[1]に記載の方法。
[6]
前記ハロゲン化アルキルおよびハロゲン化ベンジルが、ヨウ化メチル、ヨウ化エチル、および臭化ベンジルからなる群から選択される、上記[5]に記載の方法。
[7]
前記炭酸アルカリがCs 2 CO 3 であり、前記溶媒がDMFである、上記[3]、[4]、[5]、または[6]に記載の方法。
[8]
式IIの化合物と炭酸アルカリとのモル比が約3:1から約1:1であり、式IIの化合物とアルキル化剤とのモル比が約1:1から約3:1である、上記[2]、[3]、[4]、[5]、[6]、または[7]に記載の方法。
[9]
式IIの化合物と炭酸アルカリとのモル比が約2:1であり、式IIの化合物とアルキル化剤とのモル比が約1:3である、上記[8]に記載の方法。
[10]
反応の完了した混合物をCH 3 CNおよび2.5%Na 2 S 2 O 3 水溶液で希釈するステップをさらに含む、上記[9]に記載の方法。
[11]
DMFとCH 3 CNとの比が約1:1から約3:1であり、DMFと2.5%Na 2 S 2 O 3 水溶液との比が約1:2から約2:1である、上記[10]に記載の方法。
[12]
DMFとCH 3 CNとの比が約2:1であり、DMFと2.5%Na 2 S 2 O 3 水溶液との比が約1:1である、上記[11]に記載の方法。
[13]
式IIの化合物を調製する方法であって、
式I
式II
を含み、化合物Iとビス−N,O−トリメチルシリルアセトアミドとのモル比が1:1.1であり、前記接触させるステップを約22℃から約70℃で実施する、方法。
[14]
前記接触させるステップが、化合物IをCH 3 CNと接触させることをさらに含む、上記[13]に記載の方法。
[15]
前記ビス−N,O−トリメチルシリルアセトアミドで処理された反応混合物をアリールスルホニルクロリドと接触させるステップをさらに含む、上記[14]に記載の方法。
[16]
式Iの化合物とアリールスルホニルクロリドとのモル比が約1:2から約2:1である、上記[15]に記載の方法。
[17]
式Iの化合物とアリールスルホニルクロリドとのモル比が約1:1.1である、上記[16]に記載の方法。
Claims (17)
- 式IIIの化合物を製造する方法であって、
式II
式III
を含み、
R1は、
R2は、
- 前記接触させるステップが22℃と60℃の間で実施される、請求項1に記載の方法。
- 前記接触させるステップが、DMF、DMSO、DMA、NMP、およびCH3CNからなる群から選択される溶媒をさらに含む、請求項1に記載の方法。
- 前記炭酸アルカリが、Na2CO3、K2CO3、Cs2CO3、およびLi2CO3からなる群から選択される、請求項1に記載の方法。
- 前記アルキル化剤が、ハロゲン化アルキルおよびハロゲン化ベンジルからなる群から選択される、請求項1に記載の方法。
- 前記ハロゲン化アルキルおよびハロゲン化ベンジルが、ヨウ化メチル、ヨウ化エチル、および臭化ベンジルからなる群から選択される、請求項5に記載の方法。
- 前記炭酸アルカリがCs2CO3であり、前記溶媒がDMFである、請求項3、4、5、または6に記載の方法。
- 式IIの化合物と炭酸アルカリとのモル比が約3:1から約1:1であり、式IIの化合物とアルキル化剤とのモル比が約1:1から約3:1である、請求項2、3、4、5、6、または7に記載の方法。
- 式IIの化合物と炭酸アルカリとのモル比が約2:1であり、式IIの化合物とアルキル化剤とのモル比が約1:3である、請求項8に記載の方法。
- 反応の完了した混合物をCH3CNおよび2.5%Na2S2O3水溶液で希釈するステップをさらに含む、請求項9に記載の方法。
- DMFとCH3CNとの比が約1:1から約3:1であり、DMFと2.5%Na2S2O3水溶液との比が約1:2から約2:1である、請求項10に記載の方法。
- DMFとCH3CNとの比が約2:1であり、DMFと2.5%Na2S2O3水溶液との比が約1:1である、請求項11に記載の方法。
- 式IIの化合物を調製する方法であって、
式I
式II
を含み、化合物Iとビス−N,O−トリメチルシリルアセトアミドとのモル比が1:1.1であり、前記接触させるステップを約22℃から約70℃で実施する、方法。 - 前記接触させるステップが、化合物IをCH3CNと接触させることをさらに含む、請求項13に記載の方法。
- 前記ビス−N,O−トリメチルシリルアセトアミドで処理された反応混合物をアリールスルホニルクロリドと接触させるステップをさらに含む、請求項14に記載の方法。
- 式Iの化合物とアリールスルホニルクロリドとのモル比が約1:2から約2:1である、請求項15に記載の方法。
- 式Iの化合物とアリールスルホニルクロリドとのモル比が約1:1.1である、請求項16に記載の方法。
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