JP2012524726A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012524726A5 JP2012524726A5 JP2012506298A JP2012506298A JP2012524726A5 JP 2012524726 A5 JP2012524726 A5 JP 2012524726A5 JP 2012506298 A JP2012506298 A JP 2012506298A JP 2012506298 A JP2012506298 A JP 2012506298A JP 2012524726 A5 JP2012524726 A5 JP 2012524726A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- alkylene
- alkyl
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 117
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 53
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 239000012038 nucleophile Substances 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 9
- -1 1-butyl-3-methylimidazolium (BMIM) salt Chemical class 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000010520 demethylation reaction Methods 0.000 claims description 6
- 150000004965 peroxy acids Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000007944 thiolates Chemical class 0.000 claims description 4
- 229960002921 methylnaltrexone Drugs 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- ZAMAFRNSJJRKSI-UHFFFAOYSA-N 1,1-dimethyl-3-propylideneurea Chemical compound CCC=NC(=O)N(C)C ZAMAFRNSJJRKSI-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 2
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000006352 cycloaddition reaction 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 238000001212 derivatisation Methods 0.000 claims description 2
- AHRQMWOXLCFNAV-UHFFFAOYSA-O ethylammonium nitrate Chemical compound CC[NH3+].[O-][N+]([O-])=O AHRQMWOXLCFNAV-UHFFFAOYSA-O 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 239000002608 ionic liquid Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- INAXVFBXDYWQFN-XHSDSOJGSA-N morphinan Chemical compound C1C2=CC=CC=C2[C@]23CCCC[C@H]3[C@@H]1NCC2 INAXVFBXDYWQFN-XHSDSOJGSA-N 0.000 claims description 2
- PFBSOANQDDTNGJ-YNHQPCIGSA-N morphinone Chemical class O([C@H]1C(C=C[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O PFBSOANQDDTNGJ-YNHQPCIGSA-N 0.000 claims description 2
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000011669 selenium Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 239000012425 OXONE® Substances 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 claims 1
- 0 C*(*)(C1C([C@@]23)(C=CC4(O)OC)[O+])[C@]1(C1)C2C4Oc2c3c1ccc2* Chemical compound C*(*)(C1C([C@@]23)(C=CC4(O)OC)[O+])[C@]1(C1)C2C4Oc2c3c1ccc2* 0.000 description 2
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17252109P | 2009-04-24 | 2009-04-24 | |
| US61/172,521 | 2009-04-24 | ||
| PCT/CA2010/000587 WO2010121369A1 (en) | 2009-04-24 | 2010-04-22 | Processes for the preparation of morphinane and morphinone compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012524726A JP2012524726A (ja) | 2012-10-18 |
| JP2012524726A5 true JP2012524726A5 (https=) | 2013-05-16 |
| JP5824448B2 JP5824448B2 (ja) | 2015-11-25 |
Family
ID=43010633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012506298A Expired - Fee Related JP5824448B2 (ja) | 2009-04-24 | 2010-04-22 | モルフィナンおよびモルフィノン化合物の調製法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8853401B2 (https=) |
| EP (1) | EP2421868A4 (https=) |
| JP (1) | JP5824448B2 (https=) |
| KR (1) | KR20120088537A (https=) |
| CN (1) | CN102459275A (https=) |
| AU (1) | AU2010239059B2 (https=) |
| CA (1) | CA2758231A1 (https=) |
| IL (1) | IL215553A (https=) |
| MX (1) | MX2011011245A (https=) |
| NZ (1) | NZ595591A (https=) |
| WO (1) | WO2010121369A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010017573A1 (en) * | 2008-08-11 | 2010-02-18 | Tasmanian Alkaloids Pty Limited | PROCESS FOR MAKING MORPHINAN-6α-OLS |
| CN102558188B (zh) * | 2010-12-17 | 2014-07-23 | 北大方正集团有限公司 | 一种溴甲纳曲酮的制备方法 |
| CN102558189B (zh) * | 2010-12-17 | 2014-09-03 | 北大方正集团有限公司 | 溴甲纳曲酮的精制方法 |
| CA2833283A1 (en) * | 2011-05-02 | 2012-11-08 | Brock University | Processes and intermediates in the preparation of morphine analogs via n-demethylation of n-oxides using cyclodehydration reagents |
| AU2012253188B2 (en) * | 2011-05-06 | 2016-12-22 | Brock University | Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer |
| US8981098B2 (en) | 2012-02-03 | 2015-03-17 | Brock University | Process for the preparation of morphine analogs via the reaction of organometallic reagents with an oxazolidine derived from morphinans |
| US9701688B2 (en) | 2014-05-05 | 2017-07-11 | Noramco, Inc. | Process for the preparation of opioid compounds |
| US9701687B2 (en) | 2014-05-05 | 2017-07-11 | Noramco, Inc. | Process for the preparation of opioid compounds |
| EP3023427A1 (en) * | 2014-11-19 | 2016-05-25 | Siegfried AG | Improved method of manufacturing buprenorphine and analogues thereof from oripavine |
| CN105777765A (zh) * | 2014-12-15 | 2016-07-20 | 北大方正集团有限公司 | 一种乙酰化溴甲纳曲酮及其制备方法 |
| CN105777767A (zh) * | 2014-12-15 | 2016-07-20 | 北大方正集团有限公司 | 一种乙酰化Delta-7溴甲纳曲酮及其制备方法 |
| WO2018211331A1 (en) * | 2017-05-19 | 2018-11-22 | Evolva Sa | Preparation of buprenorphine |
| CN111777617B (zh) * | 2020-07-10 | 2025-06-06 | 华润三九医药股份有限公司 | 一种溴甲纳曲酮的精制方法 |
| WO2022127321A1 (zh) * | 2020-12-18 | 2022-06-23 | 四川大学 | 一种新型中间体及其制备方法和应用 |
| CN114502560B (zh) * | 2020-12-18 | 2023-06-30 | 四川大学 | 一种中间体及其制备方法和应用 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1136214A (en) | 1965-06-15 | 1968-12-11 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| US3474101A (en) | 1960-09-05 | 1969-10-21 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| US4176186A (en) | 1978-07-28 | 1979-11-27 | Boehringer Ingelheim Gmbh | Quaternary derivatives of noroxymorphone which relieve intestinal immobility |
| ES2127532T3 (es) | 1994-05-31 | 1999-04-16 | Mallinckrodt Chemical Inc | Preparacion de nalbufina con niveles bajos del epimero beta. |
| KR100204659B1 (ko) | 1996-05-28 | 1999-06-15 | 강재헌 | 신규한 부프레노핀계 진통제용 화합물 |
| AU6934400A (en) * | 1999-08-25 | 2001-03-19 | Barrett R. Cooper | Compositions and methods for treating opiate intolerance |
| US7119100B2 (en) | 2001-09-14 | 2006-10-10 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences, P.L.A. China | Oripavine derivatives and their uses as pharmaceuticals |
| DE10229842A1 (de) | 2002-07-03 | 2004-02-05 | Helmut Prof. Dr. Schmidhammer | Morphinanderivate und deren quartäre Ammoniumsalze substituiert in Position 14, Herstellungsverfahren und Verwendung |
| ATE444295T1 (de) | 2002-11-08 | 2009-10-15 | Mallinckrodt Inc | Verfahren zur herstellung von quaternäre n-alkyl morphinan alkaloid salzen |
| AR057035A1 (es) * | 2005-05-25 | 2007-11-14 | Progenics Pharm Inc | SíNTESIS DE (R)-N-METILNALTREXONA, COMPOSICIONES FARMACÉUTICAS Y USOS |
| ES2329296T3 (es) | 2006-01-05 | 2009-11-24 | Mallinckrodt, Inc. | El uso de oripavina como material de partida para buprenorfina. |
| KR101421747B1 (ko) | 2006-04-21 | 2014-07-30 | 넥타르 테라퓨틱스 | 모르피논의 입체선택적 환원 |
| FR2906252B1 (fr) | 2006-09-21 | 2008-11-28 | Sanofi Aventis Sa | Procede de preparation d'halogenures de n-aklyl naltrexone |
| US20080125592A1 (en) | 2006-10-17 | 2008-05-29 | Penick Corporation | Process for preparing oxymorphone, naltrexone, and buprenorphine |
| JP2010511726A (ja) * | 2006-12-04 | 2010-04-15 | ノランコ・インコーポレーテツド | １４−ヒドロキシコデイノンの濃度が低いオキシコドンの製造方法 |
| KR100791555B1 (ko) | 2007-02-02 | 2008-01-03 | 주식회사 선진화학 | 초미립자 무기금속산화물 수분산체 및 이의 제조방법 |
| EP2132443B1 (de) | 2007-03-06 | 2011-05-18 | ixetic Bad Homburg GmbH | Pumpe mit einem magnetisch angesteuerten schaltventil zur saugdrosselung |
| NZ579469A (en) | 2007-03-06 | 2011-02-25 | Mallinckrodt Inc | Process for the preparation of quaternary n-alkyl morphinan alkaloid salts |
| WO2008138383A1 (de) | 2007-05-16 | 2008-11-20 | Cilag Ag | Verfahren zur herstellung von n-methylnaltrexonbromid |
| US7999104B2 (en) * | 2007-06-29 | 2011-08-16 | Brock University | Methods for one-pot N-demethylation/N-acylation of morphine and tropane alkaloids |
| GB2450691A (en) | 2007-07-02 | 2009-01-07 | Alpharma Aps | One-pot preparation of oxycodone from thebaine |
| CN101570539B (zh) * | 2009-06-01 | 2012-01-11 | 漆又毛 | 一种吗啡酮季铵盐衍生物及其制备方法 |
-
2010
- 2010-04-22 KR KR1020117025806A patent/KR20120088537A/ko not_active Withdrawn
- 2010-04-22 MX MX2011011245A patent/MX2011011245A/es active IP Right Grant
- 2010-04-22 CA CA2758231A patent/CA2758231A1/en not_active Abandoned
- 2010-04-22 JP JP2012506298A patent/JP5824448B2/ja not_active Expired - Fee Related
- 2010-04-22 NZ NZ595591A patent/NZ595591A/xx not_active IP Right Cessation
- 2010-04-22 US US13/264,182 patent/US8853401B2/en not_active Expired - Fee Related
- 2010-04-22 CN CN2010800284272A patent/CN102459275A/zh active Pending
- 2010-04-22 EP EP10766555A patent/EP2421868A4/en not_active Withdrawn
- 2010-04-22 AU AU2010239059A patent/AU2010239059B2/en not_active Ceased
- 2010-04-22 WO PCT/CA2010/000587 patent/WO2010121369A1/en not_active Ceased
-
2011
- 2011-10-05 IL IL215553A patent/IL215553A/en not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012524726A5 (https=) | ||
| EP3298012B1 (en) | Synthesis of heterocyclic compounds | |
| JP6432452B2 (ja) | 縮合複素環化合物の製造方法 | |
| TWI689494B (zh) | 用於製備二芳基硫乙內醯脲化合物之方法（二） | |
| TWI645901B (zh) | 雙環烷基化合物及合成 | |
| RU2015102723A (ru) | Получение 2-(5-бром-4-(4-циклопропилнафталин-1-ил)-4h-1,2,4-триазол-3-илтио)уксусной кислоты | |
| AU2015341779B2 (en) | Synthesis of copanlisib and its dihydrochloride salt | |
| JP7744955B2 (ja) | 可溶性グアニル酸シクラーゼ刺激剤を調製するための新規のプロセスおよび中間体 | |
| KR20180038461A (ko) | 세포독성 벤조다이아제핀 유도체의 제조 방법 | |
| Boratyński et al. | Diastereoselective Corey–Chaykovsky 9-epoxymethylation of cinchona alkaloids: Access to chiral Scaffolds with diverse functionalities | |
| EP3303300B1 (en) | Process for the preparation of enzalutamide | |
| CN110028451B (zh) | 一种全取代吡唑衍生物制备方法 | |
| Wet-osot et al. | Facile synthesis of N-acylbenzotriazoles from carboxylic acids mediated by 2, 4, 6-trichloro-1, 3, 5-triazine and triethylamine | |
| Wang et al. | DMAP-promoted in situ activation of bromoacetic acid as a 2-carbon synthon for facile synthesis of pyridines and fused pyridin-2-ones | |
| WO2016071382A1 (en) | Synthesis of pi3k inhibitor and salts thereof | |
| CN103694162B (zh) | (1s,2r)-1-苯基2-(酞酰亚胺)甲基-n,n-二乙基-环丙甲酰胺的制备方法 | |
| EP2963026B1 (en) | Substituted (r)-3-(4-methylcarbamoyl-3-fluorophenylamino)tetrahydrofuran-3-enecarboxylic acid (variants) and ester thereof, method for producing and using same | |
| JPH061776A (ja) | 置換ピラジンカルボニトリルの製造方法 | |
| CN118388352A (zh) | 一种n-三氟甲基胺类化合物的制备方法 | |
| Mohadeszadeh et al. | Synthesis of New Multi-Functionalised 1, 1′-Carbonylbispyrazole Derivatives | |
| JP5881514B2 (ja) | アミン誘導体の製造方法 | |
| CN106278968B (zh) | 一种合成硫代氨基酸衍生物的方法 | |
| CN116209440A (zh) | 化合物的制造方法 | |
| CN116813618A (zh) | 一种氨基取代的咪唑并吡啶化合物及其合成方法 | |
| Shved et al. | Reactions of silyl nitronates with dimethylformamide dimethyl acetal as a new general procedure for the synthesis of 2-nitroenamines |