JP6419131B2 - ピラゾールカルボン酸アミドの製造方法 - Google Patents
ピラゾールカルボン酸アミドの製造方法 Download PDFInfo
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- JP6419131B2 JP6419131B2 JP2016217091A JP2016217091A JP6419131B2 JP 6419131 B2 JP6419131 B2 JP 6419131B2 JP 2016217091 A JP2016217091 A JP 2016217091A JP 2016217091 A JP2016217091 A JP 2016217091A JP 6419131 B2 JP6419131 B2 JP 6419131B2
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- 0 *CC(C(C1)=C(Cl)Cl)C(CCC2)=C1C2=NOC(ON=C(CCC1)C(C2CC3)=C1C3C2=C(Cl)Cl)=* Chemical compound *CC(C(C1)=C(Cl)Cl)C(CCC2)=C1C2=NOC(ON=C(CCC1)C(C2CC3)=C1C3C2=C(Cl)Cl)=* 0.000 description 3
- MZGPCLIDFPCPTI-UHFFFAOYSA-N C[n]1nc(C(F)F)c(C(Cl)=O)c1 Chemical compound C[n]1nc(C(F)F)c(C(Cl)=O)c1 MZGPCLIDFPCPTI-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/56—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by doubly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/02—Monothiocarbonic acids; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/02—Monothiocarbonic acids; Derivatives thereof
- C07C329/04—Esters of monothiocarbonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
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- Plural Heterocyclic Compounds (AREA)
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
a)式II
b)式IVの化合物を金属触媒の存在下で水素化して式V
c)式Vの化合物を還元剤の存在下で還元して式VI
d)式VIの化合物を酸の存在下で脱水して式VII
e)式VIIの化合物をヒドロキシルアミンと反応させて式VIII
及び、
f)式VIIIの化合物のオキシム酸素を、溶媒、及び、酸塩化物(例えば塩化アセチル、塩化ピバロイル、塩化ベンゾイル、又は塩化クロロアセチル)又は無水酢酸若しくは無水ピバロイル酸のような酸無水物の存在下でアシル化し、最後に、得られた生成物を式IX
によって製造することができる。
R1−C(X)−Cl(Xl)
(式中、Xは酸素又は硫黄であり、Xが酸素又は硫黄でR1が塩素であるか、Xが酸素でR1がC1〜C6のアルコキシ、CH3−C(=CH2)−O−、フェノキシ、又はトリクロロメトキシである)のアシル化剤の存在下、アシル化することと、
a)R1が塩素であり、かつ式XIの化合物が式VIIIの化合物に添加された場合、得られた式XIIa
式IX
b)R1が塩素であり、かつ式VIIIの化合物が式XIの化合物に添加された場合、若しくはXが酸素でR1がC1〜C6のアルコキシ、CH3−C(=CH2)−O−、フェノキシ、又はトリクロロメトキシの場合、得られた式XII
R1−C(X)−Cl(Xl)
(式中、Xは酸素であり、R1はC1〜C6のアルコキシ、CH3−C(=CH2)−O−、フェノキシ、又はトリクロロメトキシであり、好ましくはC1〜C6のアルコキシ、フェノキシ、又はトリクロロメトキシである)のアシル化剤の存在下、アシル化し、得られた式XII
式VIIIの化合物は、以下のように国際公開第2011/015416号パンフレットに従って製造することができる。
撹拌されているAlCl3(60.0g、0.45mol)のトルエン(200g)懸濁液に、不活性雰囲気(窒素)下、テトラヒドロフラン(46.0g、0.64mol)を20〜25℃で滴下した。透明な触媒溶液は室温で保管した。
Diels−Alder環化付加:
ガラス製反応器に、冷温の6,6−ジクロロフルベントルエン溶液(858g、0.479mol、8.2%)及び1,4−ベンゾキノン(56.9g、0.526mol)を入れた。反応器の中身を、不活性雰囲気(窒素)下、撹拌しながら−9℃に冷却した。触媒溶液(40g、7.8gのAlCl3を含有)を、−9℃で30分以内に反応器へ添加し、その後、追加的な量の触媒溶液(10g、2.0gのAlCl3を含有)を60分以内に添加した。−9℃で3.5時間撹拌した後、−9℃でエタノール(70ml)を滴下することによって反応混合物をクエンチした。反応物を−9℃で30分撹拌し、濾過した。生成物を冷温のエタノール/トルエン混合物(2:1、360ml)で洗浄し、真空乾燥した。収量102g(83%)。
1H NMR(CDCl3,400MHz)δ3.40(m,2H),4.09(m,2H),6.21(t,J=2.0Hz,2H),6.66(s,2H)。13C NMR(CDCl3,75MHz)δ47.5,49.6,103.4,134.8,142.6,147.6,196.6。
1H NMR(CDCl3,400MHz)δ1.47−1.53(m,2H),1.72−1.79(m,2H),2.51−2.60(m,2H),2.82−2.92(m,2H),3.20(m,2H),3.37(m,2H)。13C NMR(CDCl3,100MHz)δ23.7,38.8,43.9,50.5,106.9,144.0,207.8。
収量46.9g(98%、水酸基の部分で異性体である9:1の混合物)。
1H NMR(CDCl3,400MHz)δ(主異性体)1.58−1.72(m,3H),1.84(bs,1H),2.04(m,2H),2.20−2.35(m,2H),2.48−2.55(m,1H),2.74(m,2H),3.12(m,1H),3.28(m,1H),4.41(m,1H)。
1時間後、結晶混合物を更に0℃まで冷却(氷浴)し、この温度で30分維持した。生成した大きな結晶を濾過し、ヘキサン(30ml)で洗浄し、空気中で乾燥した。母液は15mlの体積まで濃縮し、追加的な目的物結晶を集めた。収量20.7g(85%)。
1H NMR(CDCl3,400MHz)δ(主異性体)1.23−1.32(m,2H),1.88−2.14(m,4H),2.23−2.30(m,1H),2.35−2.57(m,3H),3.49(m,1H),3.87(m,1H)。13C NMR(CDCl3,100MHz)δ23.3,24.2,25.0,25.7,37.4,42.2,49.6,102.3,140.7,149.2,167.1,193.7。
1H NMR(DMSO−d6,400MHz)δ(主異性体)1.17(m,1H),1.32(m,1H),1.67(m,2H),1.77−1.92(m,2H),2.14−2.31(m,3H),2.50(m,1H),3.36(d,J=3.4Hz,1H),3.64(d,J=3.3Hz,1H),10.70(s,1H)。
1H NMR(CDCl3,400MHz)δ(主異性体)1.24−1.38(m,2H),1.36(t,J=7.0Hz,3H),1.77−1.85(m,2H),1.87−2.01(m,2H),2.24(td,J=6.8及び18.4Hz,1H),2.35−2.51(m,2H),2.75(td,J=5.8及び17.2Hz,1H),3.41(dd,J=0.8及び3.3Hz,1H),3.98(d,J=3.0Hz,1H),4.31(q,J=7.1Hz,2H)。
13C NMR(CDCl3,100MHz)δ(主異性体)14.29,21.01,23.46,23.67,25.89,26.08,43.39,49.29,64.52,101.49,134.21,149.42,153.94,156.89,157.45。
融点159℃。
1H NMR(CDCl3,400MHz)δ(主異性体)1.23−1.37(m,2H),1.77−1.85(m,2H),1.86−2.01(m,2H),2.24(td,J=6.8及び18.4Hz,1H),2.37−2.50(m,2H),2.75(td, J=5.8及び17.2Hz,1H),3.42(dd,J=1.3及び3.3 Hz,1H),3.88(s,3H),3.98(d,J=3.0Hz,1H)。
13C NMR(CDCl3,100MHz)δ(主異性体)21.01, 23.46, 23.64, 25.89, 26.10, 43.39, 49.31, 55.15, 101.56, 134.16, 149.40, 154.54, 157.08, 157.61。
融点135℃。
1H NMR(CDCl3,400MHz)δ(主異性体)1.25−1.41(m,2H),1.37(d,J=7.3Hz,3H),1.39(d,J=7.1Hz,3H),1.78−1.87(m,2H),1.89−2.03(m,2H),2.25(td,J=6.8Hz,11.6Hz,1H),2.37−2.54(m,2H),2.77(td,J=5.8Hz,17.2Hz,1H),3.41(dd,J=1.3Hz,3.0Hz,1H),3.99(d,J=3.0Hz,1H),5.00(sept,J=6.3Hz,1H)。
13C NMR(CDCl3,100MHz)δ(主異性体)21.04,21.77(2C),23.46,23.73,25.91,26.09,43.39,49.29,72.68,101.48,134.30,149.45,153.51,156.71,157.31。
融点143℃。
1H NMR(CDCl3,400MHz)δ(主異性体)1.27−1.41(m,2H),1.82−1.89(m,2H),1.92−2.04(m,2H),2.28(td,J=6.8及び18.4Hz,1H),2.44(td,J=5.3及び18.4Hz,1H),2.56(td,J=7.3及び17.2Hz,1H),2.84(td,J=5.8及び17.1Hz,1H),3.46(dd,J=1.0及び3.5 Hz,1H),4.02(d,J=3.0Hz,1H),7.23−7.30(m,3H),7.36−7.45(m,2H)。
13C NMR(CDCl3,100MHz)δ(主異性体)21.04,23.50,23.80,25.90,26.10,43.42,49.36,101.68,120.95(2C),126.11,129.52(2C),134.05,149.37,151.05,152.24,157.65,158.25。
融点155℃。
1H NMR(CDCl3,400MHz)δ(主異性体)1.24−1.38(m,2H),1.78−1.86(m,2H),1.88−2.04(m,2H),2.02(s,3H),2.25(td,J=6.6及び18.5Hz,1H),2.35−2.54(m,2H),2.78(td,J=5.8及び17.2Hz,1H),3.42(dd,J=0.8及び3.3Hz,1H),3.98(d,J=3.0 Hz,1H),4.75(q,J=0.8Hz,1H),4.87(q,J=1.5Hz,1H)。
13C NMR(CDCl3,100MHz)δ(主異性体)19.12,21.01,23.46,23.71,25.88,26.08,43.37,49.32,101.58,102.34,134.05,149.37,151.54,152.91,157.40,157.95。
1H NMR(CDCl3,400MHz)1.37(m,1H),1.49(m,1H),2.09(m,2H),3.90(s,3H),3.94(m,1H),4.07(m,1H),6.91(t,JH-F=54.2Hz,1H),7.02(d,J=7.3Hz,1H),7.16(t,J=7.8Hz,1H),7.79(d,J= 8.2Hz,1H),8.01(s,1H),8.15(m,1H)。化合物3−ジフルオロメチル−1−メチル−1H−ピラゾール−4−カルボン酸[2−ジクロロメチレン−1−ヒドロキシ−3−(2−ヒドロキシ−エチル)−インダン−4−イル]−アミドは、最終生成物中に見られなかった。
Claims (5)
- 式I
の化合物の製造方法であって、前記方法は、式VIII
の化合物のオキシム酸素を、溶媒及び式XI
R1−C(X)−Cl (XI)
(式中、Xは酸素又は硫黄であり、R1が塩素である。)
のアシル化剤の存在下、アシル化することと、
a)前記式XIの化合物が前記式VIIIの化合物に添加された場合、得られた式XIIa、
(式中、Xは酸素又は硫黄である。)のアシル化された化合物を、
式IX、
の化合物と反応させること、又は、
b)前記式VIIIの化合物が前記式XIの化合物に添加される場合、得られた式XII、
(式中、Xは酸素又は硫黄であり、R1が塩素である。)のアシル化された化合物を、
式IX、
の化合物と反応させること、
を含む、方法。 - 前記アシル化された化合物が、酸の存在下で前記式IXの化合物と反応する、請求項1に記載の方法。
- 前記アシル化された化合物が、CH3SO3Hの存在下で前記式IXの化合物と反応する、請求項1に記載の方法。
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US (1) | US8895757B2 (ja) |
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KR (1) | KR101851781B1 (ja) |
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MX (1) | MX352697B (ja) |
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TWI534126B (zh) * | 2011-01-25 | 2016-05-21 | 先正達合夥公司 | 用於製備吡唑羧酸醯胺之方法 |
TWI510472B (zh) | 2012-02-15 | 2015-12-01 | Syngenta Participations Ag | 立體選擇性製備吡唑羧醯胺之方法 |
WO2018179632A1 (ja) | 2017-03-31 | 2018-10-04 | 日本精工株式会社 | レーザ溶接装置、レーザ加工装置、レーザ溶接方法、軸受の製造方法、機械の製造方法、車両の製造方法、軸受、機械、及び車両 |
WO2024017788A1 (en) | 2022-07-22 | 2024-01-25 | Syngenta Crop Protection Ag | Solid form of a heterocyclic amide derivative |
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JPS58194853A (ja) * | 1982-05-11 | 1983-11-12 | Showa Denko Kk | シクロヘキセン−アセチルオキシム誘導体 |
US5093347A (en) | 1991-01-28 | 1992-03-03 | Monsanto Company | 3-difluoromethylpyrazolecarboxamide fungicides, compositions and use |
PL1940813T3 (pl) | 2005-10-25 | 2011-04-29 | Syngenta Participations Ag | Pochodne amidowe heterocykli użyteczne jako środki mikrobiobójcze |
CN102026982A (zh) * | 2008-05-14 | 2011-04-20 | 先正达参股股份有限公司 | 制备酰胺的方法 |
MX2011006425A (es) * | 2008-12-24 | 2011-07-20 | Syngenta Ltd | Metodos para la preparacion de fungicidas. |
US8507694B2 (en) | 2009-08-06 | 2013-08-13 | Syngenta Crop Protection Llc | Process for the preparation of pyrazole carboxylic acid amides |
MX2012012005A (es) * | 2010-04-20 | 2012-12-17 | Syngenta Participations Ag | Proceso para preparar amidas de acidos carboxilicos pirazolicos. |
WO2011131546A1 (en) * | 2010-04-20 | 2011-10-27 | Syngenta Participations Ag | Process for the preparation of pyrazole carboxylic acid amides |
EP2560960B1 (en) * | 2010-04-20 | 2014-02-26 | Syngenta Participations AG | Process for the preparation of pyrazole carboxylic acid amides |
TWI534126B (zh) * | 2011-01-25 | 2016-05-21 | 先正達合夥公司 | 用於製備吡唑羧酸醯胺之方法 |
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JP2017071614A (ja) | 2017-04-13 |
KR101851781B1 (ko) | 2018-04-24 |
US8895757B2 (en) | 2014-11-25 |
IL227317A (en) | 2014-11-30 |
ES2540211T3 (es) | 2015-07-09 |
TWI534126B (zh) | 2016-05-21 |
WO2012101139A1 (en) | 2012-08-02 |
US20130310592A1 (en) | 2013-11-21 |
MX352697B (es) | 2017-12-05 |
AU2012210547A1 (en) | 2013-08-01 |
AR084915A1 (es) | 2013-07-10 |
KR20140019333A (ko) | 2014-02-14 |
MX2013007914A (es) | 2013-08-29 |
EP2668166A1 (en) | 2013-12-04 |
EP2668166B1 (en) | 2015-05-13 |
BR112013018533A2 (pt) | 2016-07-12 |
PL2668166T3 (pl) | 2015-09-30 |
AU2012210547B2 (en) | 2016-04-14 |
TW201245114A (en) | 2012-11-16 |
JP2014504596A (ja) | 2014-02-24 |
PT2668166E (pt) | 2015-08-27 |
CA2824730C (en) | 2018-10-23 |
UY33879A (es) | 2012-08-31 |
IL227317A0 (en) | 2013-09-30 |
CO6751253A2 (es) | 2013-09-16 |
CA2824730A1 (en) | 2012-08-02 |
CN103339113A (zh) | 2013-10-02 |
HRP20150658T1 (hr) | 2015-07-31 |
JP6133788B2 (ja) | 2017-05-24 |
CN103339113B (zh) | 2015-07-22 |
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