EA015949B1 - Способ получения замещённых адамантиларилмагний галогенидов - Google Patents
Способ получения замещённых адамантиларилмагний галогенидов Download PDFInfo
- Publication number
- EA015949B1 EA015949B1 EA200900899A EA200900899A EA015949B1 EA 015949 B1 EA015949 B1 EA 015949B1 EA 200900899 A EA200900899 A EA 200900899A EA 200900899 A EA200900899 A EA 200900899A EA 015949 B1 EA015949 B1 EA 015949B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- reaction
- adamantyl
- mol
- adamantylaryl
- halide
- Prior art date
Links
- 150000004820 halides Chemical class 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title description 7
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 17
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 57
- 229910052749 magnesium Inorganic materials 0.000 claims description 26
- 239000011777 magnesium Substances 0.000 claims description 26
- -1 1-adamantyl Chemical group 0.000 claims description 24
- 238000003747 Grignard reaction Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 abstract description 14
- 239000012039 electrophile Substances 0.000 abstract description 10
- 238000003786 synthesis reaction Methods 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 229910052786 argon Inorganic materials 0.000 abstract description 7
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 238000004817 gas chromatography Methods 0.000 description 42
- 150000004795 grignard reagents Chemical class 0.000 description 25
- 239000007818 Grignard reagent Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- QQAMHHZQONQBFZ-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)adamantane Chemical compound COC1=CC=C(Br)C=C1C1(C2)CC(C3)CC2CC3C1 QQAMHHZQONQBFZ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 7
- STGNTTPGWSZTMO-UHFFFAOYSA-N 1-(5-bromo-2,3-dimethoxyphenyl)adamantane Chemical compound COC1=CC(Br)=CC(C23CC4CC(CC(C4)C2)C3)=C1OC STGNTTPGWSZTMO-UHFFFAOYSA-N 0.000 description 6
- 150000001502 aryl halides Chemical class 0.000 description 6
- HYSZKSPAPGPYFQ-UHFFFAOYSA-N 1-(2-methoxyphenyl)adamantane Chemical compound COC1=CC=CC=C1C1(C2)CC(C3)CC2CC3C1 HYSZKSPAPGPYFQ-UHFFFAOYSA-N 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- FRPWQGROGLXUPZ-UHFFFAOYSA-N 1-(4-bromo-2-methoxyphenyl)adamantane Chemical compound COC1=CC(Br)=CC=C1C1(C2)CC(C3)CC2CC3C1 FRPWQGROGLXUPZ-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000004792 aryl magnesium halides Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002901 organomagnesium compounds Chemical class 0.000 description 3
- 125000002734 organomagnesium group Chemical group 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- SETWKWMHYWYXJD-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)-3,5-dimethyladamantane Chemical compound COC1=CC=C(Br)C=C1C1(C2)CC(C)(C3)CC2(C)CC3C1 SETWKWMHYWYXJD-UHFFFAOYSA-N 0.000 description 2
- LDGIHZJOIQSHPB-UHFFFAOYSA-N CD437 Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3C=C2)C(=O)O)=CC=C1O LDGIHZJOIQSHPB-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- HOXDQGKKENOCRK-UHFFFAOYSA-M [Br-].C1C(C2)CC(C3)CC2CC13C1=CC([Mg+])=CC=C1OCC1=CC=CC=C1 Chemical compound [Br-].C1C(C2)CC(C3)CC2CC13C1=CC([Mg+])=CC=C1OCC1=CC=CC=C1 HOXDQGKKENOCRK-UHFFFAOYSA-M 0.000 description 2
- AIYARUNZTVUMQC-UHFFFAOYSA-M [Br-].CC(C)(C)[Si](C)(C)OC1=CC=C([Mg+])C=C1C1(C2)CC(C3)CC2CC3C1 Chemical group [Br-].CC(C)(C)[Si](C)(C)OC1=CC=C([Mg+])C=C1C1(C2)CC(C3)CC2CC3C1 AIYARUNZTVUMQC-UHFFFAOYSA-M 0.000 description 2
- 229960002916 adapalene Drugs 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- ZUIMAMHUQKPCBR-QHHAFSJGSA-N (e)-3-[4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorophenyl]prop-2-enoic acid Chemical compound ClC1=CC(/C=C/C(=O)O)=CC=C1C1=CC=C(O)C(C23CC4CC(CC(C4)C2)C3)=C1 ZUIMAMHUQKPCBR-QHHAFSJGSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- INULLDUIYAKZOH-UHFFFAOYSA-N 1-(4-bromo-2-phenylmethoxyphenyl)adamantane Chemical compound C=1C(Br)=CC=C(C23CC4CC(CC(C4)C2)C3)C=1OCC1=CC=CC=C1 INULLDUIYAKZOH-UHFFFAOYSA-N 0.000 description 1
- GVLSPHCBVZUIKP-UHFFFAOYSA-N 1-(5-bromo-2-phenylmethoxyphenyl)adamantane Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(Br)=CC=C1OCC1=CC=CC=C1 GVLSPHCBVZUIKP-UHFFFAOYSA-N 0.000 description 1
- OYGKAJLOXWVEGP-UHFFFAOYSA-N 4-(1-adamantyl)-6-bromo-1,3-benzodioxole Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(Br)=CC2=C1OCO2 OYGKAJLOXWVEGP-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 101000581326 Homo sapiens Mediator of DNA damage checkpoint protein 1 Proteins 0.000 description 1
- 102100027643 Mediator of DNA damage checkpoint protein 1 Human genes 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- FPZOBRFHRPQGAA-UHFFFAOYSA-N [3-(1-adamantyl)-4-methoxyphenyl]boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1C1(C2)CC(C3)CC2CC3C1 FPZOBRFHRPQGAA-UHFFFAOYSA-N 0.000 description 1
- YBJABQLZUJNFKS-UHFFFAOYSA-N [3-(1-adamantyl)-4-methoxyphenyl]methanol Chemical compound COC1=CC=C(CO)C=C1C1(C2)CC(C3)CC2CC3C1 YBJABQLZUJNFKS-UHFFFAOYSA-N 0.000 description 1
- UVRUWTVOTRHEDA-UHFFFAOYSA-N [4-(1-adamantyl)-3-methoxyphenyl]boronic acid Chemical compound COC1=CC(B(O)O)=CC=C1C1(C2)CC(C3)CC2CC3C1 UVRUWTVOTRHEDA-UHFFFAOYSA-N 0.000 description 1
- CMFAVTSZPVDNME-UHFFFAOYSA-M [Br-].COC1=CC=C([Mg+])C=C1C1(C2)CC(C3)CC2CC3C1 Chemical compound [Br-].COC1=CC=C([Mg+])C=C1C1(C2)CC(C3)CC2CC3C1 CMFAVTSZPVDNME-UHFFFAOYSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LV060151A LV13735B (en) | 2006-12-28 | 2006-12-28 | Method for manufacturing substituted adamantylarylmagnesium chalogenides |
| PCT/EP2007/064648 WO2008080993A2 (fr) | 2006-12-28 | 2007-12-28 | Procédé de préparation d'halogénures d'adamantylarylmagnésium substitués |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200900899A1 EA200900899A1 (ru) | 2010-02-26 |
| EA015949B1 true EA015949B1 (ru) | 2011-12-30 |
Family
ID=39589040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200900899A EA015949B1 (ru) | 2006-12-28 | 2007-12-28 | Способ получения замещённых адамантиларилмагний галогенидов |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP2129679A2 (fr) |
| EA (1) | EA015949B1 (fr) |
| LV (1) | LV13735B (fr) |
| UA (1) | UA97507C2 (fr) |
| WO (1) | WO2008080993A2 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113866292B (zh) * | 2021-09-13 | 2024-03-19 | 河北威远生物化工有限公司 | 一种邻氯苄基氯化镁含量的测定方法 |
| CN117511212B (zh) * | 2023-11-09 | 2024-04-12 | 东莞市好易达新材料科技有限公司 | 一种耐高温的硅树脂玻璃纤维套管和制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100348569C (zh) | 2001-11-30 | 2007-11-14 | 伯哈姆学院 | 癌细胞中编程性细胞死亡的诱导 |
| EP1582523A1 (fr) | 2004-04-02 | 2005-10-05 | Ludwig-Maximilians-Universität München | Procédé de préparation de composés organomagnésiens |
-
2006
- 2006-12-28 LV LV060151A patent/LV13735B/lv unknown
-
2007
- 2007-12-28 EA EA200900899A patent/EA015949B1/ru not_active IP Right Cessation
- 2007-12-28 UA UAA200907979A patent/UA97507C2/ru unknown
- 2007-12-28 WO PCT/EP2007/064648 patent/WO2008080993A2/fr active Application Filing
- 2007-12-28 EP EP07858234A patent/EP2129679A2/fr not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| LIU, ZHICHANG ET AL.: "A high yield and pilot-scale process for the preparation of adapalene" ORGANIC PROCESS RESEARCH & DEVELOPMENT, 10(2), 285-288 CODEN: OPRDFK; ISSN: 1083-6160, 2006, XP002498088 transformation of compound 5 to 7 * |
Also Published As
| Publication number | Publication date |
|---|---|
| UA97507C2 (ru) | 2012-02-27 |
| LV13735B (en) | 2008-09-20 |
| EP2129679A2 (fr) | 2009-12-09 |
| WO2008080993A3 (fr) | 2009-03-12 |
| WO2008080993A2 (fr) | 2008-07-10 |
| EA200900899A1 (ru) | 2010-02-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |