1017553-74-0|2-(Pyridin-3-yl)cyclopropanecarboxylic acid| Ambeed

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Quality Control of [ 1017553-74-0 ] Purity: 95% SDS Specification

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Product Details of [ 1017553-74-0 ]

CAS No. :	1017553-74-0
Formula :	C₉H₉NO₂
M.W :	163.17
SMILES Code :	O=C(C1C(C2=CC=CN=C2)C1)O
MDL No. :	MFCD11934488
InChI Key :	RMVMPLYFCJXMCQ-UHFFFAOYSA-N
Pubchem ID :	21901282

Safety of [ 1017553-74-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501

Application In Synthesis of [ 1017553-74-0 ]

* 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 [ 1017553-74-0 ]

[ 1017553-74-0 ] Synthesis Path-Downstream 1~35

1
[ 132414-81-4 ]
[ 1017553-74-0 ]
tert-butyl trans-1-(2-(pyridin-3-yl)cyclopropanecarbonyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate [ No CAS ]
tert-butyl trans-1-(2-(pyridin-3-yl)cyclopropanecarbonyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

2
[ 1017553-74-0 ]
[ 200484-41-9 ]
trans-N-(6-(4-chlorophenoxy)hexyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

3
[ 1041756-57-3 ]
[ 1017553-74-0 ]
trans-N-(4-(1-benzoylpiperidin-4-yl)butyl)-2-(pyridin-3-yl)-cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

4
[ 1017553-74-0 ]
[ 94341-56-7 ]
trans-N-(4-(phenylsulfonyl)benzyl)-2-(pyridin-3-yl)-cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

5
[ 626-55-1 ]
[ 1017553-74-0 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.
[2]Patent: WO2016/36636,2016,A1 .
[3]Patent: CN108530444,2018,A .
[4]Patent: CN110938109,2020,A .

6
[ 100390-47-4 ]
[ 1017553-74-0 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.
[2]Patent: CN110938109,2020,A .

7
(E)-3-(pyridin-3-yl)acrylic acid [ No CAS ]
[ 1017553-74-0 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.
[2]Patent: WO2017/195216,2017,A1 .
[3]Patent: CN110938109,2020,A .
[4]Patent: CN111848506,2020,A .
[5]Patent: CN113717159,2021,A .

8
[ 1455271-42-7 ]
[ 1017553-74-0 ]

9
N-methoxy-N-methyl-2-(pyridin-3-yl)cyclopropane-1-carboxamide [ No CAS ]
[ 1017553-74-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	With lithium hydroxide monohydrate; potassium hydroxide; In ethanol; at 20℃; for 16h;	To a stirred solution of N-methoxy-N-methyl-2-(pyridin-3-yl)cyclopropane-1-carboxamide (XLVII, 0.9 g, 4.3mmol) in water (2 mL) andethanol (1 mL) was addedpotassium hydroxide (0.731 g, 13mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction was concentrated under vacuum and then acidified to pH 5 with 2Naqueous HC1. The resultant crude was concentrated under vacuum and then methanol (5 mL) was added to it. The resultant solid was filtrated and the filtrate was concentrated under vacuum to get the title product as colourless sticky oil (XLVIII, 0.45 g, 64%). LC-MS m/z calcd for C9H9N02, 163.1; found 164.1 [M+H]+.
54%	With lithium hydroxide monohydrate; potassium hydroxide; In ethanol; at 20℃; for 24h;	Dissolve KOH (647 mg, 11.6 mmol) in 10 mL of water, then add aqueous KOH solution to 29a (800 g, 3.88 mmol)In ethanol (15mL) solution, stirred at room temperature for 24h.After the reaction is complete, add 10 mL of water, extract with DCM (3 × 5 mL), adjust the pH of the aqueous phase to 6.0 with 12M HCl solution,Then spin off the water under reduced pressure, dry the solid obtained in vacuum and add methanol to beat (20mL),Filtration was performed to remove insoluble solids by suction filtration, and the filtrate was concentrated to obtain a pale yellow solid.Recrystallization from ethyl acetate / methanol (5: 1) gave pure product 30a (341 mg, 54%).
54%	With potassium hydroxide; In ethanol; lithium hydroxide monohydrate; at 20℃; for 24h;	KOH (647 mg, 11.6 mmol) was dissolved in 10 mL of water, and then the KOH aqueous solution was added to the ethanol (15 mL) solution of 14a (800 g, 3.88 mmol) and stirred at room temperature for 24 h. After the reaction is complete, add 10 mL of water, extract with DCM (3×5 mL), adjust the pH of the aqueous phase to 6.0 with 12M HCl solution, then spin off the water under reduced pressure, vacuum dry the resulting solid, add methanol to make a slurry (20 mL), filter to remove insoluble The obtained solid was suction filtered, and the filtrate was concentrated to obtain a pale yellow solid. Recrystallization from ethyl acetate/methanol (5:1) gave pure 15a (341mg, 54%).

54%	With ethanol; lithium hydroxide monohydrate; potassium hydroxide; at 20℃; for 24h;	KOH (647 mg, 11.6 mmol) was dissolved in 10 mL of water, then KOH aqueous solution was added to a solution of 17a (800 g, 3.88 mmol) in ethanol (15 mL), and stirred at room temperature for 24 h. After the reaction was completed, 10 mL of water was added, extracted with DCM (3×5 mL), and the aqueous phase was adjusted with 12M HCl solutionThe pH was adjusted to 6.0, then the water was removed under reduced pressure, the solid obtained by vacuum drying was added to methanol and slurried (20 mL), the insoluble solid was filtered off to obtain suction filtration, and the filtrate was concentrated to obtain a pale yellow solid. Recrystallization from ethyl acetate/methanol (5:1) gave pure 18a (341 mg, 54%).
	With potassium hydroxide; In ethanol; lithium hydroxide monohydrate; for 3h;Reflux;	3-bromopyridine (157 g, 0.994 mol) under nitrogen.N-butyl acrylate (192 g, 1.50 mmol), Pd(OAc) 2 (2.3 g, 10.2 mmol,), PPh3 (5.2 g, 19.8 mmol), K2CO3 (276 g, 2.00 mol) was added to DMF (200 ml).Heat to 130 C for 20 h.Cool to room temperature, filter, concentrate the filtrate, add water, ethyl acetate (500ml×3).The mixture was washed with brine, dried over anhydrous sodium sulfateCompound 8 (70 g, 0.34 mol) was dissolved in ethanol (150 ml).Potassium hydroxide (40 g, 0.71 mol) was dissolved in water (150 ml) and added to the above solution.Heated to reflux for 3 h. After the reaction was over, the pH was adjusted to 6.0 with 12 M HCl.Precipitation was precipitated, filtered, and the filter cake was collected to give compound 9 (50 g, 98%).Compound 9 (50 g, 0.34 mol) and N,O-dimethylhydroxylamine hydrochloride (65 g, 0.67 mol)Dissolved in dichloromethane (1 L), then added EDCI (127 g, 0.66 mol)With DMAP (80 g, 0.65 mol), the reaction was stirred at room temperature for 2 h.After the reaction was completed, 200 ml of water was added, and extraction with dichloromethane (1 L × 2) was carried out.The organic phase was combined and the organic phase was washed with brine (500 ml×3).Dry over anhydrous sodium sulfate and concentrate to give a crude compound (yield 70 g).Trimethylthioiodo (145 g, 0.67 mol) was dissolved in DMSO (500 ml).Sodium hydrogen (26 g, 1.1 mol) was added to the above solution at 0 C.Transfer to room temperature, stir for 1 h, then add compound 10 (66 g, 0.34 mol) to the solution described above.The reaction was continued at room temperature for 1 h. After completion of the reaction, it was quenched by the addition of a saturated ammonium chloride solution (400 mL).Extracted with ethyl acetate (3×1 L), combined organics, washed with water (3×500 mL)Drying over anhydrous sodium sulfate, EtOAc (EtOAc)Compound 11 (50 g, 0.24 mol) was dissolved in ethanol.Potassium hydroxide (40 g, 0.71 mol) was dissolved in water (100 mL) and added to the above solution.After heating to reflux for 3 h, after completion of the reaction, water (300 mL) and dichloromethane (3×100 mL)The aqueous phase was adjusted to pH 6.0 with 12 M HCl, then the aqueous phase was concentrated to give a solid.Methanol was added to the solid, the insoluble matter was filtered off, and the filtrate was concentrated.34 g of pale yellow crude compound 12 were obtained.Compound 12 (1.0 g, 6.13 mmol) was dissolved in anhydrous dichloromethane (5 mL)Thionyl chloride (10 mL, 138 mmol) was added, 1 drop of DMF, heated to 40 C, and reacted for 5 h.It was cooled to room temperature and concentrated to give a crude compound 13 ( 1.34 g).Compound II-1 was dissolved in anhydrous DMF and triethylamine (1.0 g, 10 mmol) was added.The prepared acid chloride compound 13 (0.18 g, 0.99 mmol) was dissolved in anhydrous DMF.It was added dropwise to II-1 (461.82 mg, 1.29 mmol) and allowed to react at room temperature for 4 h.The reaction solution is concentrated,Column chromatography gave the title compound (149 mg, 30%).

References: [1]Patent: WO2017/195216,2017,A1 .Location in patent: Page/Page column 155.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.
[3]Patent: CN110938109,2020,A .Location in patent: Paragraph 0263-0264; 0273-0274.
[4]Patent: CN111848506,2020,A .Location in patent: Paragraph 0216-0217; 0222-0223.
[5]Patent: CN113717159,2021,A .Location in patent: Paragraph 0134-0135; 0140-0141.
[6]Patent: CN108530444,2018,A .Location in patent: Page/Page column 98; 99.

10
[ 1017553-74-0 ]
trans-N-(4-(phenylsulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

11
[ 1017553-74-0 ]
[ 1541193-81-0 ]
[ 1541193-82-1 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

12
[ 1017553-74-0 ]
trans-N-(4-(morpholinosulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

13
[ 1017553-74-0 ]
trans-N-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-ylsulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

14
[ 1017553-74-0 ]
trans-2-(pyridin-3-yl)-N-(4-((tetrahydro-2H-pyran-4-yl)sulfonyl)phenyl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

15
[ 1017553-74-0 ]
trans-N-(4-((6-methylpyridin-3-yl)sulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

16
[ 1017553-74-0 ]
trans-N-(4-((3-(methylsulfonyl)phenyl)sulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

17
[ 1017553-74-0 ]
trans-2-(pyridin-3-yl)-N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

18
[ 1017553-74-0 ]
trans-2-(pyridin-3-yl)-N-(4-((3-(trifluoromethyl)phenyl)sulfonyl)phenyl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

19
[ 1017553-74-0 ]
trans-N-(4-((3,5-difluorophenyl)sulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

20
[ 1017553-74-0 ]
trans-N-(4-((1-ethyl-1H-pyrazol-4-yl)sulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

21
[ 1017553-74-0 ]
trans-2-(pyridin-3-yl)-N-(4-((1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)sulfonyl)phenyl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

22
[ 1017553-74-0 ]
trans-N-(4-((1-propyl-1H-pyrazol-4-yl)sulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

23
[ 1017553-74-0 ]
trans-N-(4-((1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl)sulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

24
[ 1017553-74-0 ]
trans-N-(4-((1-isopropyl-1H-pyrazol-4-yl)sulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

25
[ 1017553-74-0 ]
[ 1541194-04-0 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

26
[ 1017553-74-0 ]
trans-N-(4-((1-isopropyl-3-methyl-1H-pyrazol-4-yl)sulfonyl)phenyl)-2-(pyridin-3-yl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

27
[ 1017553-74-0 ]
trans-2-(pyridin-3-yl)-N-(4-((1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl)sulfonyl)phenyl)cyclopropanecarboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.

28
[ 1017553-74-0 ]
2-(pyridin-3-yl)cyclopropane-1-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 40℃; for 5h;	3-bromopyridine (157 g, 0.994 mol) under nitrogen.N-butyl acrylate (192 g, 1.50 mmol), Pd(OAc) 2 (2.3 g, 10.2 mmol,), PPh3 (5.2 g, 19.8 mmol), K2CO3 (276 g, 2.00 mol) was added to DMF (200 ml).Heat to 130 C for 20 h.Cool to room temperature, filter, concentrate the filtrate, add water, ethyl acetate (500ml×3).The mixture was washed with brine, dried over anhydrous sodium sulfateCompound 8 (70 g, 0.34 mol) was dissolved in ethanol (150 ml).Potassium hydroxide (40 g, 0.71 mol) was dissolved in water (150 ml) and added to the above solution.Heated to reflux for 3 h. After the reaction was over, the pH was adjusted to 6.0 with 12 M HCl.Precipitation was precipitated, filtered, and the filter cake was collected to give compound 9 (50 g, 98%).Compound 9 (50 g, 0.34 mol) and N,O-dimethylhydroxylamine hydrochloride (65 g, 0.67 mol)Dissolved in dichloromethane (1 L), then added EDCI (127 g, 0.66 mol)With DMAP (80 g, 0.65 mol), the reaction was stirred at room temperature for 2 h.After the reaction was completed, 200 ml of water was added, and extraction with dichloromethane (1 L × 2) was carried out.The organic phase was combined and the organic phase was washed with brine (500 ml×3).Dry over anhydrous sodium sulfate and concentrate to give a crude compound (yield 70 g).Trimethylthioiodo (145 g, 0.67 mol) was dissolved in DMSO (500 ml).Sodium hydrogen (26 g, 1.1 mol) was added to the above solution at 0 C.Transfer to room temperature, stir for 1 h, then add compound 10 (66 g, 0.34 mol) to the solution described above.The reaction was continued at room temperature for 1 h. After completion of the reaction, it was quenched by the addition of a saturated ammonium chloride solution (400 mL).Extracted with ethyl acetate (3×1 L), combined organics, washed with water (3×500 mL)Drying over anhydrous sodium sulfate, EtOAc (EtOAc)Compound 11 (50 g, 0.24 mol) was dissolved in ethanol.Potassium hydroxide (40 g, 0.71 mol) was dissolved in water (100 mL) and added to the above solution.After heating to reflux for 3 h, after completion of the reaction, water (300 mL) and dichloromethane (3×100 mL)The aqueous phase was adjusted to pH 6.0 with 12 M HCl, then the aqueous phase was concentrated to give a solid.Methanol was added to the solid, the insoluble matter was filtered off, and the filtrate was concentrated.34 g of pale yellow crude compound 12 were obtained.Compound 12 (1.0 g, 6.13 mmol) was dissolved in anhydrous dichloromethane (5 mL)Thionyl chloride (10 mL, 138 mmol) was added, 1 drop of DMF, heated to 40 C, and reacted for 5 h.It was cooled to room temperature and concentrated to give a crude compound 13 ( 1.34 g).Compound II-1 was dissolved in anhydrous DMF and triethylamine (1.0 g, 10 mmol) was added.The prepared acid chloride compound 13 (0.18 g, 0.99 mmol) was dissolved in anhydrous DMF.It was added dropwise to II-1 (461.82 mg, 1.29 mmol) and allowed to react at room temperature for 4 h.The reaction solution is concentrated,Column chromatography gave the title compound (149 mg, 30%).
	With thionyl chloride; In dichloromethane; at 40℃; for 5h;	To a DCM solution of 30a (341 mg, 2.1 mmol) was added dichlorosulfoxide (0.35 mL, 4.8 mmol), and the temperature was raised to 40 C. Reaction 5h.After the reaction is completed, the solvent is turned off to obtain the off-white crude product 31a, which is directly put into the next reaction.
	With thionyl chloride; In dichloromethane; at 40℃; for 5h;	KOH (647 mg, 11.6 mmol) was dissolved in 10 mL of water, and then the KOH aqueous solution was added to the ethanol (15 mL) solution of 14a (800 g, 3.88 mmol) and stirred at room temperature for 24 h. After the reaction is complete, add 10 mL of water, extract with DCM (3×5 mL), adjust the pH of the aqueous phase to 6.0 with 12M HCl solution, then spin off the water under reduced pressure, vacuum dry the resulting solid, add methanol to make a slurry (20 mL), filter to remove insoluble The obtained solid was suction filtered, and the filtrate was concentrated to obtain a pale yellow solid. Recrystallization from ethyl acetate/methanol (5:1) gave pure 15a (341mg, 54%).

With thionyl chloride; In dichloromethane; at 40℃; for 5h;

To a solution of 18a (341 mg, 2.1 mmol) in DCM was added thionyl chloride (0.35 mL, 4.8 mmol) and the temperature was raised to 40C. The reaction was carried out for 5 hours. After the reaction is completed, spin off the solvent to obtain the off-white crude product 19a, which is directly put into the next reaction.

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 770 - 792.
[2]Patent: CN108530444,2018,A .Location in patent: Page/Page column 98; 99.
[3]Patent: CN110938109,2020,A .Location in patent: Paragraph 0263-0264; 0275-0276.
[4]Patent: CN111848506,2020,A .Location in patent: Paragraph 0216-0217; 0224-0225.
[5]Patent: CN113717159,2021,A .Location in patent: Paragraph 0134-0135; 0142-0143.

29
[ 59607-98-6 ]
[ 1017553-74-0 ]

References: [1]Patent: WO2016/36636,2016,A1 .

30
ethyl 2-(pyridin-3-yl)cyclopropanecarboxylate [ No CAS ]
[ 1017553-74-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water;Reflux;	NaOH (50 g, 1.25 mol, 2.00 equiv) in H20 (50 g) was added to a solution of ethyl 2-(pyridin-3-yl)cyclopropanecarboxylate (75 g, 392.67 mmol, 1.00 equiv) in THF (1000 ml). The resulting reaction mixture was refluxed overnight in an oil bath. The reaction mixture was cooled to room temperature and filteredthrough CELITE, and the filter cake was washed with THF. A filtration was performed. The filter cake was washed with THF. Adjustment of the pH to 2 was accomplished by the addition of HC1. A filtration was performed. The residue was dissolved in MeOH. A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The resulting mixture was washed with CH3COCH3. The resulting compound was obtained after evaporating the filtrate in vacuo. MS: [M+HCl] 200.

References: [1]Patent: WO2016/36636,2016,A1 .Location in patent: Page/Page column 26; 27.

31
[ 1017553-74-0 ]
[ 38330-80-2 ]
3-oxo-3-(2-pyridin-3-yl-cyclopropyl)propionic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		52d) 3-Oxo-3-(2-pyridin-2-yl-cyclopropyl)-propionic acid methyl ester 1 ,10-carbonyldiimidazole (0.33 g, 2.02 mmol) was added portionwise over 5 min to a stirred solution of 2-pyridin-3-yl-cyclopropanecarboxylic acid (0.30 g, 1 .84 mmol) in anhydrous THF (5 mL) under argon. After 1 h, a mixture of MgCI2 (0.35 g, 3.68 mmol) and potassium hydrogen methyl malonate (0.86 g, 5.52 mmol) was added. After 7 h the mixture was concentrated under vacuum and diluted with ethyl acetate. The mixture was then washed with aqueous NaHS04 (1 M) and brine, and the organic phase dried over Na2S04, filtered, and concentrated to dryness to give the product, used without further purification (0.335 g, 83%). LC-MS m/z 220 (M + H) +, 0.99 (ret. time).

References: [1]Patent: WO2017/60854,2017,A1 .Location in patent: Page/Page column 261; 262.

32
[ 500-22-1 ]
[ 1017553-74-0 ]

References: [1]Patent: WO2017/60854,2017,A1 .

33
[ 81124-48-3 ]
[ 1017553-74-0 ]

References: [1]Patent: WO2017/60854,2017,A1 .

34
2-pyridin-3-yl-cyclopropanecarboxylic acid methyl ester [ No CAS ]
[ 1017553-74-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With water; lithium hydroxide; In tetrahydrofuran; methanol; for 4h;	52c) 2-Pyridin-3-yl-cyclopropanecarboxylic acid A stirred solution of 2-pyridin-3-yl-cyclopropanecarboxylic acid methyl ester (0.50 g, 2.82 mmol) in THF/MeOH (1 :1 , 14 mL) was treated with a solution of LiOH (0.604 g, 14.1 mmol) in water (14 mL). After 4 hours the reaction was diluted with water and the pH adjusted to pH4 (aqueous citric acid 5%). The mixture was extracted with IPA:CHCI3 (1 :3, x3) and the combined organic layers washed with brine, dried over MgS04, filtered, and concentrated to dryness. Purification by silica chromatography eluting with EtOAc/petrol gave the product (0.30 g, 65%). LC-MS m/z 164 (M + H) +, 0.24 (ret. time).

References: [1]Patent: WO2017/60854,2017,A1 .Location in patent: Page/Page column 261.
[2]Journal of Medicinal Chemistry,2021,vol. 64,p. 15949 - 15972.

35
[ 1017553-74-0 ]
C₁₅H₁₈N₂O₃ [ No CAS ]

References: [1]Patent: WO2017/60854,2017,A1 .

Historical Records

Technical Information

• Arndt-Eistert Homologation • Halogenation • Heat of Combustion • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

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[ 1017553-74-0 ]

Carboxylic Acids

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[ 1017553-74-0 ]

Pyridines

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Similarity: 0.91

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 1017553-74-0

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