JP5963222B2 - Ｄｆｍｂ誘導体の製造方法 - Google Patents
Ｄｆｍｂ誘導体の製造方法 Download PDFInfo
- Publication number
- JP5963222B2 JP5963222B2 JP2014556900A JP2014556900A JP5963222B2 JP 5963222 B2 JP5963222 B2 JP 5963222B2 JP 2014556900 A JP2014556900 A JP 2014556900A JP 2014556900 A JP2014556900 A JP 2014556900A JP 5963222 B2 JP5963222 B2 JP 5963222B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- group
- dfmb
- mixture
- 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.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 28
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000003849 aromatic solvent Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- PURNIHSRWGYONZ-UHFFFAOYSA-N 2-(difluoromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(C(F)F)=NC2=C1 PURNIHSRWGYONZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- GZKHDVAKKLTJPO-UHFFFAOYSA-N ethyl 2,2-difluoroacetate Chemical compound CCOC(=O)C(F)F GZKHDVAKKLTJPO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- -1 nitro, methoxy group Chemical group 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 28
- 239000007787 solid Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 23
- PBWZKZYHONABLN-UHFFFAOYSA-M difluoroacetate Chemical compound [O-]C(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-M 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 238000004817 gas chromatography Methods 0.000 description 15
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 10
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000004293 19F NMR spectroscopy Methods 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 2
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- ZMIBIIAWFMCVFD-UHFFFAOYSA-N 2,2-difluoroacetamide Chemical compound NC(=O)C(F)F ZMIBIIAWFMCVFD-UHFFFAOYSA-N 0.000 description 1
- PFJLHSIZFYNAHH-UHFFFAOYSA-N 2,2-difluoroethyl acetate Chemical compound CC(=O)OCC(F)F PFJLHSIZFYNAHH-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- CSSYKHYGURSRAZ-UHFFFAOYSA-N methyl 2,2-difluoroacetate Chemical compound COC(=O)C(F)F CSSYKHYGURSRAZ-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- YSWLZODWSKQJNC-UHFFFAOYSA-N propan-2-yl 2,2-difluoroacetate Chemical compound CC(C)OC(=O)C(F)F YSWLZODWSKQJNC-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2012/071346 WO2013123634A1 (en) | 2012-02-20 | 2012-02-20 | Process for production of dfmb derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015506991A JP2015506991A (ja) | 2015-03-05 |
| JP5963222B2 true JP5963222B2 (ja) | 2016-08-03 |
Family
ID=49004911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014556900A Expired - Fee Related JP5963222B2 (ja) | 2012-02-20 | 2012-02-20 | Ｄｆｍｂ誘導体の製造方法 |
Country Status (6)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI572228B (zh) * | 2015-03-05 | 2017-02-21 | 宏達國際電子股份有限公司 | 行動裝置與其功能執行方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2326624A1 (de) * | 1973-05-25 | 1974-12-12 | Hoechst Ag | Neue benzimidazolderivate |
| US4122184A (en) * | 1973-09-14 | 1978-10-24 | Eli Lilly And Company | Benzimidazole insecticides |
| GB9518552D0 (en) | 1995-09-11 | 1995-11-08 | Fujisawa Pharmaceutical Co | New heterocyclic compounds |
| JP4077054B2 (ja) * | 1996-05-24 | 2008-04-16 | 三共アグロ株式会社 | ベンゾチアゾール及びベンゾオキサゾール誘導体の製法 |
| US20040224952A1 (en) | 2003-05-07 | 2004-11-11 | Cowart Marlon D. | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| CN100415721C (zh) * | 2005-11-10 | 2008-09-03 | 上海大学 | 含氟硝基苯并咪唑的制备方法 |
| CN100344614C (zh) * | 2005-11-10 | 2007-10-24 | 上海大学 | 2－二氟甲基氨基苯并咪唑及其制备方法 |
| US20070244110A1 (en) * | 2006-04-14 | 2007-10-18 | Zenyaku Kogyo Kabushiki Kaisha | Treatment of prostate cancer, melanoma or hepatic cancer |
| EP2057147A1 (en) * | 2006-09-14 | 2009-05-13 | Astra Zeneca AB | Pyrimidine derivatives |
| WO2008032077A1 (en) * | 2006-09-14 | 2008-03-20 | Astrazeneca Ab | Pyrimidine derivatives |
| CN100465166C (zh) * | 2007-02-09 | 2009-03-04 | 上海大学 | 5-甲基-2-二氟甲基苯并噁唑及其合成方法 |
| CN101016274A (zh) * | 2007-02-09 | 2007-08-15 | 上海大学 | 5－氯－2－二氟甲基苯并噁唑及其合成方法 |
| CN101016276A (zh) * | 2007-02-09 | 2007-08-15 | 上海大学 | 5－硝基－2－二氟甲基苯并咪唑及其合成方法 |
| US20120165309A1 (en) | 2009-02-12 | 2012-06-28 | Astellas Pharma Inc. | Hetero ring derivative |
| US8461158B2 (en) * | 2009-03-27 | 2013-06-11 | Pathway Therapeutics Inc. | Pyrimidinyl and 1,3,5-triazinyl benzimidazole sulfonamides and their use in cancer therapy |
| PL2471786T3 (pl) | 2009-08-07 | 2016-04-29 | Chugai Pharmaceutical Co Ltd | Pochodna aminopirazolu |
| ES2523503T3 (es) * | 2010-03-04 | 2014-11-26 | Bayer Intellectual Property Gmbh | 2-Amidobencimidazoles sustituidos con fluoroalquilo y su uso para el aumento de la tolerancia al estrés en plantas |
-
2012
- 2012-02-20 IN IN7014DEN2014 patent/IN2014DN07014A/en unknown
- 2012-02-20 US US14/377,056 patent/US9458119B2/en not_active Expired - Fee Related
- 2012-02-20 EP EP12869026.0A patent/EP2817294B1/en not_active Not-in-force
- 2012-02-20 JP JP2014556900A patent/JP5963222B2/ja not_active Expired - Fee Related
- 2012-02-20 CN CN201280070516.2A patent/CN104487424A/zh active Pending
- 2012-02-20 WO PCT/CN2012/071346 patent/WO2013123634A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015506991A (ja) | 2015-03-05 |
| EP2817294B1 (en) | 2017-12-27 |
| IN2014DN07014A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-04-10 |
| US9458119B2 (en) | 2016-10-04 |
| EP2817294A4 (en) | 2015-07-29 |
| WO2013123634A1 (en) | 2013-08-29 |
| CN104487424A (zh) | 2015-04-01 |
| US20150005505A1 (en) | 2015-01-01 |
| EP2817294A1 (en) | 2014-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101821090B1 (ko) | Ｎ-아실비페닐 알라닌의 제조 방법 | |
| JP4386723B2 (ja) | 新規方法 | |
| KR101472686B1 (ko) | 벤즈이미다졸 유도체의 제조방법 | |
| DK2906531T3 (en) | APPLICABLE COMPOUNDS IN THE SYNTHESIS OF BENZAMIDE COMPOUNDS | |
| CN113402424A (zh) | 一种氰基丙烯酸酯类化合物的合成方法 | |
| TW201918475A (zh) | 一種亞托敏（Ａｚｏｘｙｓｔｒｏｂｉｎ）的製備方法 | |
| JP5963222B2 (ja) | Ｄｆｍｂ誘導体の製造方法 | |
| JP4770826B2 (ja) | ２−オキシインドール誘導体の製造法 | |
| CN115197261B (zh) | 噁二氮杂硼衍生物的合成方法 | |
| JP4587202B2 (ja) | フェニルオキサジアゾール類の製造法 | |
| CN107954960B (zh) | 一种1,3-二氢异苯并呋喃类化合物的合成方法 | |
| EP1431278A1 (en) | Process for producing (2-nitrophenyl)acetonitrile derivative and intermediate therefor | |
| JPH0641135A (ja) | イミダゾプテリジン誘導体及びその製造方法 | |
| JP5463051B2 (ja) | １，４―ジヒドロピリジン誘導体の製造法 | |
| JPWO2007119361A1 (ja) | キナゾリン−４−オン誘導体の製造方法 | |
| JP4032861B2 (ja) | β−オキソニトリル誘導体又はそのアルカリ金属塩の製法 | |
| WO2003014067A1 (en) | PROCESS FOR PRODUCING ß-OXONITRILE COMPOUND OR ALKALI METAL SALT THEREOF | |
| JPH061776A (ja) | 置換ピラジンカルボニトリルの製造方法 | |
| KR100850558B1 (ko) | 아토르바스타틴의 효율적인 제조방법 | |
| WO2011158813A1 (ja) | N－置換－２－アミノ－４－(ヒドロキシメチルホスフィニル)－２－ブテン酸の製造法 | |
| CN108822057B (zh) | 一种ae活性酯的合成方法 | |
| JP4561635B2 (ja) | ４−アルコキシカルボニルテトラヒドロピラン又はテトラヒドロピラニル−４−カルボン酸の製法 | |
| JP5148188B2 (ja) | バルビツール酸化合物 | |
| KR100967341B1 (ko) | 카바페넴 합성 중간체의 제조방법 | |
| CN114436803A (zh) | 一种3-(4-氯苯基)-1,5-二苯基戊烷-1,5-二酮化合物的制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150116 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150813 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150825 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20151125 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151211 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160524 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160622 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5963222 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |