16883-16-2|5-Methyl-3-phenylisoxazole-4-carbonyl chloride| Ambeed

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Structure of 16883-16-2

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Quality Control of [ 16883-16-2 ] Purity: 98% SDS Specification

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Product Details of [ 16883-16-2 ]

CAS No. :	16883-16-2
Formula :	C₁₁H₈ClNO₂
M.W :	221.64
SMILES Code :	O=C(Cl)C1=C(C)ON=C1C2=CC=CC=C2
MDL No. :	MFCD00052205

Safety of [ 16883-16-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P280-P305+P351+P338-P310
Class:	8
UN#:	3265
Packing Group:	Ⅱ

Application In Synthesis of [ 16883-16-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 16883-16-2 ]

[ 16883-16-2 ] Synthesis Path-Downstream 1~54

1
[ 16883-16-2 ]
[ 4340-44-7 ]

References: [1]Gazzetta Chimica Italiana,1937,vol. 67,p. 589,599.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 193 - 196.

2
[ 6494-19-5 ]
[ 16883-16-2 ]
[ 62235-34-1 ]

References: [1]Pharmazie,1976,vol. 31,p. 775 - 777.

3
[ 1136-45-4 ]
[ 16883-16-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With thionyl chloride; for 3h;Heating / reflux;	Example 1; 3-(5-Methyl-3-phenyl-isoxazol-4-yl)-imidazo[l,5-a]pyridinea) S-Methyl-S-phenyl-isoxazole-φcarboxyric acid (pyridin-2-ylmethyl)-amide A mixture of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (4.06 g, 20 mmol, commercially available) and thionyl chloride (5 mL) was heated under reflux for 3 h. Evaporation of all volatiles afforded 5-methyl-3-phenyl-isoxazole-4-carboxylic acid chloride (4.4 g, 93%) as yellow oil, which was used without further purification in the next reaction. To a mixture of an aqueous solution of 2-picolylamine (0.182 g, 1.68 mmol) in water (2 mL) and ethyl acetate (4 mL) were added sodium hydrogen carbonate (362 mg, 4.2 mmol) in one portion. Then 5-methyl-3-phenyl-isoxazole-4-carboxylic acid chloride (0.31 g, 1.4 mmol) in ethyl acetate (2 mL) was added dropwise with vigorous stirring under ice-bath cooling keeping the temperature at 0 0C. After addition, the reaction mixture was stirred at room temperature for 18 h. The resulting solution was then diluted with ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined extracts were then washed with brine, dried over sodium sulphate, and concentrated to afford the title compound (0.38 g, 93%) as a white solid. MS: m/e: 294.1 [M+H]+.
93%	With thionyl chloride; for 3h;Reflux;	A mixture of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid (l .Og, 4.9mmol, commercially available) and thionyl chloride (5ml) was heated under reflux for 3 h. Removal of excess volatiles by evaporation afforded 5-methyl-3-phenyl-isoxazole-4-carbonyl chloride (1.01 g, 93%) as a yellow oil, which was used without further purification in the next reaction.
	With phosphorus pentachloride; In dichloromethane; for 1h;Heating / reflux;	A solution of 5-methyl-3-phenylisoxazole-4-carboxylic acid (1 g) and PCIS (1 g) in dichloromethane (20 mL) was refluxed for one hour. Then dichloromethane and POCI3 were removed under reduced pressure to give 5-methyl-3-phenylisoxazole-4-carbonyl chloride.

	With thionyl chloride;	EXAMPLE 8 5-Methyl-3-phenyl-isoxazole-4-carbonyl Chloride. 5-Methyl-3-phenyl-isoxazole-4-carboxylic acid (0.54 g, 2.56 mmol) was treated with SOCl2 (2 mL) at 70 C. for 1 hr. Concentration in vacuum gave a yellow oil which was used without purification.
	With thionyl chloride; at 60℃; for 0.5h;Neat (no solvent);	Example 13 N,N-Diethyl-5-methyl-3-phenylisoxazole-4-carboxamide To 3-phenyl-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60 C. After 30 min, excess thionyl chloride was evaporated and neat diethylamine was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (20 mg). HRMS (ESI, pos. ion) m/z calcd for C15H18N2O2: 258.1368, found 258.1378.; Example 14 N,N-Diisopropyl-5-methyl-3-phenylisoxazole-4-carboxamide To 3-phenyl-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60 C. After 30 min, excess thionyl chloride was evaporated and neat diisopropylamine was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (15 mg). HRMS (ESI, pos. ion) m/z calcd for C17H22N2O2: 286.1681, found 286.1678.; Example 15 4-(Azetidin-1-ylcarbonyl)-5-methyl-3-phenylisoxazole To 3-phenyl-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60 C. After 30 min, excess thionyl chloride was evaporated and neat trimethylene imine was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (18 mg). HRMS (ESI, pos. ion) m/z calcd for C14H14N2O2: 242.1055, found 242.1063.

References: [1]Patent: WO2007/74089,2007,A1 .Location in patent: Page/Page column 10.
[2]Patent: WO2013/171334,2013,A1 .Location in patent: Page/Page column 23.
[3]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 621 - 627.
[4]Helvetica Chimica Acta,1976,vol. 59,p. 2074 - 2099.
[5]Journal of Organic Chemistry,1985,vol. 50,p. 5660 - 5666.
[6]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 193 - 196.
[7]Tetrahedron,2007,vol. 63,p. 12195 - 12201.
[8]Patent: WO2005/33103,2005,A1 .Location in patent: Page/Page column 37.
[9]Patent: US2003/149051,2003,A1 .
[10]Patent: US2008/21022,2008,A1 .Location in patent: Page/Page column 56.
[11]Journal of the American Chemical Society,2012,vol. 134,p. 12928 - 12931.
[12]Organic Letters,2014,vol. 16,p. 5266 - 5268.
[13]Journal of Medicinal Chemistry,2019,vol. 62,p. 8284 - 8310.
[14]Journal of Agricultural and Food Chemistry,2020,vol. 68,p. 10550 - 10559.

4
[ 123-75-1 ]
[ 16883-16-2 ]
[ 106833-69-6 ]

References: [1]Heterocycles,1986,vol. 24,p. 401 - 412.

5
[ 110-91-8 ]
[ 16883-16-2 ]
[ 55153-42-9 ]

References: [1]Heterocycles,1986,vol. 24,p. 401 - 412.

6
[ 5725-79-1 ]
[ 16883-16-2 ]
[ 90515-57-4 ]

References: [1]Pharmazie,1984,vol. 39,p. 86 - 91.

7
[ 16883-16-2 ]
[ 24922-32-5 ]
[ 90515-60-9 ]

References: [1]Pharmazie,1984,vol. 39,p. 86 - 91.

8
[ 16883-16-2 ]
[ 59813-07-9 ]
[ 124953-38-4 ]

References: [1]Arzneimittel-Forschung/Drug Research,1989,vol. 39,p. 642 - 646.

9
[ 16883-16-2 ]
[ 53855-57-5 ]
[ 90515-58-5 ]

References: [1]Pharmazie,1984,vol. 39,p. 86 - 91.

10
[ 16883-16-2 ]
[ 90515-46-1 ]
[ 90515-61-0 ]

References: [1]Pharmazie,1984,vol. 39,p. 86 - 91.

11
[ 16883-16-2 ]
[ 90836-45-6 ]
[ 90539-22-3 ]

References: [1]Pharmazie,1984,vol. 39,p. 86 - 91.

12
[ 16883-16-2 ]
[ 90515-48-3 ]
[ 90515-62-1 ]

References: [1]Pharmazie,1984,vol. 39,p. 86 - 91.

13
[ 16883-16-2 ]
[ 108-18-9 ]
[ 106833-71-0 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃;	To 3-phenyl-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60 C. After 30 min, excess thionyl chloride was evaporated and neat diethylamine was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (20 mg). HRMS (ESI, pos. ion) m/z calcd for C15H18N2O2: 258.1368, found 258.1378.

References: [1]Heterocycles,1986,vol. 24,p. 401 - 412.
[2]Patent: US2008/21022,2008,A1 .Location in patent: Page/Page column 56.

14
[ 16883-16-2 ]
[ 75-65-0 ]
5-methyl-3-phenyl-isoxazole-4-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

References: [1]Synthetic Communications,1998,vol. 28,p. 2337 - 2342.

15
[ 16883-16-2 ]
[ 22179-80-2 ]
C₁₈H₁₃Cl₂N₃O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 601 - 615.

16
[ 16883-16-2 ]
[ 180468-20-6 ]
(2R,3R)-3-[(5-methyl-3-phenylisoxazole-4-carbonyl)amino]-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxoazetidine-2-sulfonic acid [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 3985 - 3993.

17
[ 16883-16-2 ]
[ 180468-23-9 ]
(2R,3S)-3-[(5-methyl-3-phenylisoxazole-4-carbonyl)amino]-1-(1'-methoxycarbonyl-2'-methylpropenyl)-4-oxoazetidine-2-sulfonic acid [ No CAS ]

References: [1]Tetrahedron,2000,vol. 56,p. 3985 - 3993.

18
[ 16883-16-2 ]
methyl 1-(4-methoxyphenyl)sulfonyl-4-(tert-butoxycarbonyl)piperazine-2-carboxylate hydrochloride [ No CAS ]
1-(4-methoxy-benzenesulfonyl)-4-(5-methyl-3-phenyl-isoxazole-4-carbonyl)-piperazine-2-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 369 - 380.

19
[ 16883-16-2 ]
[ 109-89-7 ]
[ 313392-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃;	To 3-phenyl-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60 C. After 30 min, excess thionyl chloride was evaporated and neat diethylamine was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (20 mg). HRMS (ESI, pos. ion) m/z calcd for C15H18N2O2: 258.1368, found 258.1378.

References: [1]Patent: US2008/21022,2008,A1 .Location in patent: Page/Page column 56.

20
[ 503-29-7 ]
[ 16883-16-2 ]
[ 1003558-71-1 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃;	To 3-phenyl-5-methylisoxazol-4-carboxylic acid (25 mg, 0.10 mmol) was added thionyl chloride (1 mL) and the neat solution allowed to stir 60 C. After 30 min, excess thionyl chloride was evaporated and neat diethylamine was added and allowed to stir overnight at ambient temperature. The residue was purified using reversed phase HPLC to afford the title compound (20 mg). HRMS (ESI, pos. ion) m/z calcd for C15H18N2O2: 258.1368, found 258.1378.

References: [1]Patent: US2008/21022,2008,A1 .Location in patent: Page/Page column 56.

21
[ 16883-16-2 ]
1-(4-methoxy-benzenesulfonyl)-4-(5-methyl-3-phenyl-isoxazole-4-carbonyl)-piperazine-2-carboxylic acid hydroxyamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 369 - 380.

22
[ 16883-16-2 ]
[ 93599-37-2 ]