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Preparation method of oxathiapiprolin

A technology of thiazolidinone and thiazole, which is applied in the field of preparation of thiazolidinone, can solve the problems of expensive raw materials and high synthesis cost of the original drug, and achieve the advantages of easy-to-obtain raw materials, good industrial application prospects, and high reaction yield Effect

Pending Publication Date: 2022-07-01
CAC NANTONG CHEM
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  • Abstract
  • Description
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Problems solved by technology

The reaction conditions of this synthesis route are relatively mild, but the raw materials are expensive, and the whole reaction yield is only about 25%, and the whole synthesis cost of the original drug is relatively high

Method used

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  • Preparation method of oxathiapiprolin
  • Preparation method of oxathiapiprolin
  • Preparation method of oxathiapiprolin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] 1.1 Synthesis of compound 3

[0077]

[0078] Weigh 7.725g compound 1 (25mmol, content≥99%), 3.86g compound 2 (20mmol, content≥99%), 98.1mg catalyst XPhos-Pd-G2 (0.125mmol) in a 100mL reaction flask, add to it Two equivalents of 1.8 mol / L potassium carbonate aqueous solution (28 mL) and 20 mL of ethanol were reacted in the reaction flask at 75 °C for 10 h under argon protection. After the reaction was completed, it was cooled to room temperature, and ethanol was removed under reduced pressure; the residue was extracted with ethyl acetate (3×20 mL), the extracts were combined, and the ethyl acetate was removed under reduced pressure; the residue was subjected to silica gel column chromatography (petroleum ether:acetic acid) ethyl ester = 3:1) to give product 4.91 g in 83% yield.

[0079] 1 H NMR (400MHz, CDCl 3 )δ7.18(s,1H),6.08(t,J=7.4Hz,1H),4.30(d,J=7.6Hz,2H),3.95(s,2H),3.44(br,1H),2.97- 2.65(m, 2H), 2.36-1.85(m, 2H), 1.52(s, 9H).

[0080] 1.2 Synthesis of comp...

Embodiment 2

[0110] 2.1 Synthesis of compound 3

[0111]

[0112] Weigh 15.45g compound 1 (50mmol, content≥99%), 9.65g compound 2 (50mmol, content≥99%), 0.3925g catalyst XPhos-Pd-G2 (0.5mmol) in a 500mL reaction flask, add to it Three equivalents of 1.8 mol / L potassium carbonate aqueous solution (84 mL) and 200 mL of ethanol were reacted in the reaction flask at 80 °C for 15 h under argon protection. After the reaction was completed, it was cooled to room temperature, and ethanol was removed under reduced pressure; the residue was extracted with ethyl acetate (3×80 mL), the extracts were combined, and the ethyl acetate was removed under reduced pressure; the residue was subjected to silica gel column chromatography (petroleum ether:acetic acid) ethyl ester = 3:1) to give the product 13.02 g in 88% yield.

[0113] 1 H NMR (400MHz, CDCl 3 )δ7.18(s,1H),6.08(t,J=7.4Hz,1H),4.30(d,J=7.6Hz,2H),3.95(s,2H),3.44(br,1H),2.97- 2.65(m, 2H), 2.36-1.85(m, 2H), 1.52(s, 9H).

[0114] 2.2 Synthesis ...

Embodiment 3

[0138] 3.1 Synthesis of compound 3

[0139]

[0140] Weigh 30.9g compound 1 (100mmol, content≥99%), 23.16g compound 2 (120mmol, content≥99%), 7.85g catalyst XPhos-Pd-G2 (10mmol) in a 1000mL reaction flask, add 4 An equivalent of 1.8 mol / L potassium carbonate aqueous solution (224 mL) and 300 mL of ethanol were reacted in the reaction flask at 85 °C for 20 h under argon protection. After the reaction was completed, it was cooled to room temperature, and ethanol was removed under reduced pressure; the residue was extracted with ethyl acetate (3×100 mL), the extracts were combined, and the ethyl acetate was removed under reduced pressure; the residue was subjected to silica gel column chromatography (petroleum ether:acetic acid) ethyl ester = 3:1) to give product 25.75 g in 87% yield.

[0141] 3.2 Synthesis of compound 4

[0142]

[0143] 25.75g compound 3 (87mmol, chromatographic purity ≥ 95%) of the obtained reaction product in 1.1 were all put into a 200mL hydrogenatio...

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Abstract

The invention provides a preparation method of oxathiapiprolin. The method starts from cheaper raw materials, the target compound is finally obtained through eight steps of reaction including substitution, reduction, oxidation, oximation, cyclization, deprotection, acylation and substitution, the raw materials are easy to obtain in the whole reaction process, the price is low, the reaction yield is high, the raw material 4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane-2-yl)-5, 6-dione is taken as the raw material, and the target compound can be prepared through one-step synthesis of the 4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane-2-yl)-5, 6-dione. According to calculation of the 2, 6-dihydropyridine-1 (2H)-carboxylic acid tert-butyl ester, the whole reaction yield can reach 40% or above, and the method has a good industrial application prospect.

Description

technical field [0001] The invention belongs to the field of agricultural disease control and relates to a preparation method of fluthiazopyridone. Background technique [0002] Oxathiapiprohin is the first piperidinyl thiazole isoxazoline fungicide newly developed by DuPont, and the test code is DPX-QGU42. The trade name of the fungicide is Zorvec, CAS registration number is: 1003318-67-9, CAS English name: 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1 ,2-oxazol-3-yl]-1.3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]ethanone; Chinese name :1-{4-[4-(5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl)-2-thiazolyl]-1-piperidinyl} -2-(5-Methyl-3-trifluoromethyl-1H-pyrazol-1-yl)ethanone. Its structure includes oxazole ring, pyrazole ring and thiazole ring, the chemical structure is as follows: [0003] [0004] Fluthiazopyridone has very favorable toxicological and environmental properties, with low dosage and high safety to users, agricultural...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14
CPCC07D417/14
Inventor 阳海谢艳军杨丙连庞怀林
Owner CAC NANTONG CHEM
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