Name: 55151-91-2|2-(3-Methyl-1,2,4-oxadiazol-5-yl)acetic acid|95%
Brand: Ambeed
SKU: A767245
Rating: 91 (26 reviews)

1
[ 908094-01-9 ]
[ 55151-91-2 ]
(3-methyl-1,2,4-oxadiazol-5-yl)acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; water	5 methyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate EXAMPLE 5 methyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate A solution of an excess of diazomethane in diethyl ether was added to a stirred, cold (about 2° C.) solution of 14 g of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid in 500 ml of diethyl ether. After the initially vigorous evolution of nitrogen was finished, the solution was concentrated on the steam bath to about 250 ml. The solution was washed three times with 100 ml of water and the wash waters were combined, adjusted to a pH of 9.0 and were extracted with diethyl ether to obtain the part of the product which dissolved in water during the washings. The combined ethereal extracts were filtered through a water repelling paper filter and then were evaporated in vacuo. After keeping the residue for 1 hour at 8 mm the residual oil weighed 14.8 g. The yellow oil was distilled at 0.4-0.5 mm and the collected fraction with a boiling point 70°-71° C. to obtain 12.3 g of methyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate with a refractive index nD25 =1.4472. PMR (60 Mc, CDCl3, TMS as internal reference, δ-values in ppm): 2.38 (s, 3H), 3.76 (s, 3H), 3.99 (s, 2H). IR (NaCl windows, values in cm-1): 3020, 2985, 2870, 1760 and 1600.

Reference： [1]Current Patent Assignee: BAIN CAPITAL INC - US4160829, 1979, A

2
[ 55151-91-2 ]
[ 111-70-6 ]
n-heptyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In water	36 n-heptyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate EXAMPLE 36 n-heptyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate Under anhydrous conditions, a stream of gaseous hydrochloric acid was passed through 25 ml of n-heptanol and as soon as a saturated solution was reached at room temperature, 5.7 g (0.04 mol) of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid were introduced. Introduction of a slow stream of hydrochloric acid was continued for two hours and the reaction mixture was then stirred for 60 hours at room temperature whereby conversion of the carboxylic acid was virtually completed. The reaction mixture was thoroughly mixed with 75 ml of cold water and the layers were separated. The organic layer was washed three times with 10 ml volumes of a saturated solution of sodium bicarbonate in water, and two times with 10 ml of cold water. All water-layers were combined and extracted twice with 20 ml volumes of ethyl acetate. The combined ethyl acetate extracts were once washed with 10 ml of iced water and the water-layers were discarded. The two organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was distilled and fractionated at reduced pressure to obtain 6.8 g of n-heptyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate of about 95% molar purity (impurity mainly a small amount of n-heptanol with a b.p. of 108° C. at 0.25 mm Hg and a refractive index nD20 =1.450. IR (NaCl windows, values in cm-1): 2940, 2860, 1745, 1590, 1465, 1440 (sh), 1395, 1350, 1290, +-1250, 1200, 740. PMR (CDCl3, 60 Mc, TMS, δ-values in ppm): 0.88 (distorted triplet, 3H), from about 1.0 to 1.9 (broad absorption area, 10H), 2.38 (s, 3H), 3.93 (s, 2H), 4.17 (t, J=6.4 cps, 2H).

Reference： [1]Current Patent Assignee: BAIN CAPITAL INC - US4160829, 1979, A

3
[ 1072-67-9 ]
decarboxylate [ No CAS ]
[ 55151-91-2 ]
phosphorous trichloride (PCl₃) [ No CAS ]
N-{(5-methyl)-isoxazol-3-yl}-3-methyl-1,2,4-oxadiazol-5-ylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.7%	With phosphorus trichloride In 1,4-dioxane; water; toluene	20 N-{(5-methyl)-isoxazol-3-yl}-3-methyl-1,2,4-oxadiazol-5-ylacetamide EXAMPLE 20 N-{(5-methyl)-isoxazol-3-yl}-3-methyl-1,2,4-oxadiazol-5-ylacetamide The method employed below is in essence outlined in "Houben-Weyl, Methoden der Organischen Chemie", Band 11/2, p. 5 and 6. 7.8 g (0.055 mol) of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid were dissolved in 80 ml of a dry solvent mixture consisting of equal volume parts of dioxane and toluene. 6.9 g (0.07 mol) of 5-methyl-3-amino-isoxazole dissolved in 50 ml of the same mixture of dioxane and toluene and 4.2 g (0.031 mol) of phosphorous trichloride (PCl3) were successively added thereto. After the addition of PCl3, the mixture became lukewarm and a deposit of a heavy yellowish oil was noticed. Within a very short time, crystallization of the oil took place and the mixture was heated for 5 minutes at 90° C. on the steam-bath. Afterwards, the mixture was additionally stirred for 60 minutes at room temperature and then was evaporated in vacuo. The residue was suspended in 80 ml of water and the acidic suspension (pH of 1.5) was heated for 60 minutes on the steam-bath to decarboxylate remnants of the oxadiazolyl-acetic acid. The suspension was cooled and was continuously extracted with dichloromethane for 16 hours. The obtained extract was cooled to room temperature and the resulting mixture of crystals and solution were completely evaporated. The crystalline residue was dissolved in a slight excess of dichloromethane and the resulting solution was slowly cooled to room temperature, and then successively to 3° C., -15° C. and finally to -70° C. The crystals were quickly vacuum filtered, washed with dichloromethane at -70° C. and finally with n-heptane. After drying in vacuo, the N-{(5-methyl)-isoxazol-3-yl}-3-methyl-1,2,4-oxadiazol-5-yl-acetamide weighed 10.45 g (85.7% yield based on 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid) and had a m.p. of 191°-193° C. IR: (KBr-disc, values in cm-1): 3240, 3290, 1715, 1650, 1605, 1585, 1500, 1450, 1365, 1280, 1220, 1045, 940, 900, 750 and 650. PMR: (about 4:1 mixture of CDCl3 and d6 -DMSO, 60 Mc,δ-values in ppm, TMS as reference): (s) and narrow d together at 2.4 (6H), 4.1 (s, 2H), 6.58 (narrow q, 1H), 10.5 (slightly broad s, 1H).

Reference： [1]Current Patent Assignee: BAIN CAPITAL INC - US4160829, 1979, A

4
[ 55151-91-2 ]
[ 15892-23-6 ]
sec.-butyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%		26 Sec.-butyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate EXAMPLE 26 Sec.-butyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate Using the procedure of Example 17, 12 g of phosphorous oxychloride were slowly added to a mixture of 12 g of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid and 8.9 g of dry sec.-butanol and the rate of addition was adjusted to a reaction temperature of 65°+-5° C. The resulting reaction mixture was stirred for 90 minutes at 65° C., and then treated as in Example 17. The product was distilled at 68° C. and 1.5 mm Hg to obtain 6.1 g (35% yield) of sec.-butyl 3-methyl-1,2,4-oxadiazol-5-yl-acetate. The purity of the final product was about 95% (according to TLC and PMR spectrum) and it had a refractive index nD25 =1.438. IR: (NaCl windows, values in cm-1): 3000, 2960, 2900, 1745, 1600. PMR: (60 Mc, CDCl3, TMS, δ-values in ppm): 0.9 (triplet like, J=7.0 cps, 3H), 1.25 (d, J=6.3 cps, 3H), about 1.55 (quintet like, 2H), 2.40 (s, 3H), 3.93 (s, 2H), 4.93 (regular sextet, J=6.2 cps, 1H).

Reference： [1]Current Patent Assignee: BAIN CAPITAL INC - US4160829, 1979, A

5
fur-2-yl-carbonyl-hydrazide [ No CAS ]
[ 55151-91-2 ]
phosphorus trichloride [ No CAS ]
N-(fur-2-yl-carbonyl)-3-methyl-1,2,4-oxadiazol-5-yl-acethydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With pyridine In 1,4-dioxane; water; toluene	23 N'-(fur-2-yl-carbonyl)-3-methyl-1,2,4-oxadiazol-5-yl-acethydrazide EXAMPLE 23 N'-(fur-2-yl-carbonyl)-3-methyl-1,2,4-oxadiazol-5-yl-acethydrazide The employed method is an adaptation of the method outlined in "Houben-Weyl, Methoden der Organischen Chemie", Band 11/2, p. 5 and 6. Under anhydrous conditions and with powerful mechanical stirring, 5 g (0.063 mol) of pyridine and 6.3 g (0.05 mol) of fur-2-yl-carbonyl-hydrazide were added at room temperature successively to a solution of 6 g (0.042 mol) of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid in a mixture of 50 ml of dry dioxane and 50 ml of toluene. To the resulting clear solution was added all at once 3.4 g (0.025 mol) of phosphorous trichloride and a heavy, yellow oil appeared which solidified quickly. Subsequently, the reaction mixture was heated for 5 minutes at about 90° C. on the steam-bath followed by stirring at room temperature for 60 minutes. The reaction mixture was evaporated in vacuo and the residue was suspended in 75 ml of water. The acidic suspension at pH 2 was heated for 60 minutes on the steam-bath which resulted in a clear yellow solution. After cooling the solution to room temperature, crystallization of a yellowish solid took place and this product was isolated by vacuum filtration and was washed with ice-water. The product weighed 7.2 g and was recrystallized from acetone with step-wise cooling down to about -20° C. to obtain 5.1 g (about 46% yield) of a slight yellow crystalline solid of about 95% purity (according to TLC and PMR) of N-(fur-2-yl-carbonyl)-3-methyl-1,2,4-oxadiazol-5-yl-acethydrazide, m.p. of 169°-171° C. IR: (KBr-disc, values in cm-1): +-3180, 1700 and 1675, 1620, +-1590, +-1570, +-1510, 1480, 1435, 1205, 945 and 790. PMR: (d6 -DMSO, 60 Mc, δ-values in ppm, DSS as reference): 2.36 (s, 3H), 4.04 (s, 2H), 6.65 (q, J=3.6 and J'=1.7 cps, 1H), 7.25 (q, J=3.6 and J"=0.7 cps, 1H), 7.9 (q, J'=1.7 and J"=0.7 cps, 1H), 10.35 (s, about 1.8H).

Reference： [1]Current Patent Assignee: BAIN CAPITAL INC - US4160829, 1979, A

6
[ 55151-91-2 ]
phosphorus trichloride [ No CAS ]
3-methyl-1,2,4-oxadiazol-5-yl-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.5%	With ammonia In 1,4-dioxane; diethyl ether; dichloromethane; water; toluene	21 3-methyl-1,2,4-oxadiazol-5-yl-acetamide EXAMPLE 21 3-methyl-1,2,4-oxadiazol-5-yl-acetamide The employed method is an adaptation of the method outlined in "Houben-Weyl, Methoden der Organischen Chemie", Band 11/2, p. 5 and 6. 8 g (0.056 M) of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid were dissolved at room temperature in 150 ml of a dry solvent mixture consisting of equal volume parts of dioxane and toluene and at room temperature, 3.5 g of dry, gaseous ammonia were introduced into the solution which resulted in the precipitation of the ammonium salt of the oxadiazolyl-acetic acid in the form of a white thick slush. While gaseous ammonia was introduced slowly below the surface of the vigorously stirred mixture, a solution of 4 g (0.029 mol) of phosphorous trichloride in 50 ml of the same solvent mixture of dioxane and toluene was introduced over a period of 10 minutes. During the addition, the mixture became lukewarm and attained a yellowish color. Then, the reaction mixture was heated at about 90° C. on the steam-bath for 5 minutes and the reaction mixture was stirred for 60 minutes at room temperature and then completely evaporated in vacuo. The residue was dissolved in 75 ml of water, and the resulting acidic solution (pH 2.0) was heated for 60 minutes on the steam-bath. The solution was cooled to room temperature, was saturated with sodium chloride and then continuously extracted for 16 hours with dichloromethane. The obtained extract was completely evaporated resulting in a crystalline residue which resisted several recrystallization attempts from various solvents. Therefore, the residue was filtered through a short silica column with diethyl ether. Ether was removed and the residue was recrystallized from a 9:1 mixture of diethyl ether and dichloromethane employing step-wise cooling of the solution from room temperature down to -70° C. (crystals washed with very cold diethyl ether) to obtain 5.1 g (64.5% yield) of 3-methyl-1,2,4-oxadiazol-5-yl-acetamide with a m.p. of 77°-77.5° C. IR: (KBr-disc, values in cm-1): 3180, +-3240, 1685, +-1635, 1595, 1445 (s), 1425, 1400, 1360, 1315, 1270, 1260, 1180, 1060, 890, 730 and 685. PMR: (CDCl3 and a trace of d6 DMSO, 60 Mc, δ-values in ppm, TMS as reference): 2.40 (s, 3H), 3.88 (s, 2H), +-6.6 and +-7.2 (centres of 2 broad abs., about 2H).

Reference： [1]Current Patent Assignee: BAIN CAPITAL INC - US4160829, 1979, A

7
[ 10403-80-2 ]
[ 55151-91-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; nitrogen In diethyl ether; hexane; chloroform; water; Petroleum ether	1 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid EXAMPLE 1 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid A solution of 4.0 g (40.8 mmol) of 3,5-dimethyl-1,2,4-oxadiazole and of 6.0 ml of N,N,N',N'-tetramethylethylenediamine (TMEDA) in 100 ml of dry toluene was prepared in a 250 ml three-necked glass vessel equipped with a thermometer, a gas inlet tube through which dry nitrogen was introduced continuously and a pressure equalized dropping funnel. The magnetically stirred solution was cooled to -75° C. with an acetone-carbon dioxide bath and by means of the dropping funnel, a solution of approximately 40 mmol of n-butyllithium in 20 ml of n-hexane was added slowly to keep the reaction mixture below -65° C. Afterwards the reaction mixture was stirred for another 60 minutes at -55° to -60° C. Subsequently, the reaction mixture was transferred with a bent ground glass tube to a second vessel containing powdered carbon dioxide covered with a layer of dry diethyl ether and after standing a few hours, the carbon dioxide had practically disappeared from the mixture. 100 ml of water were added, followed by addition of 1 N hydrochloric acid with stirring until a pH of 8 was attained. The layers were separated and the organic layer was discarded and the aqueous layer was shaken twice with 25 ml of diethyl ether. The pH of the aqueous layer was brought to 2.0 with 1 N hydrochloric acid and seven extractions with about 25 ml portions of ethyl acetate at pH 2.0 resulted in almost complete removal of the desired product from the aqueous layer. The extracts were combined, dried over anhydrous magnesium sulfate, and filtered and the filtrate was concentrated in vacuo to a small volume until a crystalline white precipitate appeared. Thin-layer chromatography showed that the supernatant liquid still contained a considerable amount of the desired product and no by-products and the solvent was then completely removed in vacuo. The practically colorless residue was dried to constant weight to obtain 4.2 g (72% yield) of the product with a purity of at least 96% estimated by TLC and PMR spectrum. Recrystallization of the product was effected by dissolution in a minimum volume of chloroform, followed by slow addition of petroleum ether (b.p. 80°-110° C.) until a turbidity appear to obtain 3.6 g of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid with a melting point of about 95° C. (slow decarboxylation sets in at about 90° C.). pKa -value (determined in water): 3.64 Analysis: C5 H6 N2 O3: Calculated: %C 42.26, %H 4.26, %N 19.71, %O 33.77. Found: %C 42.24, %H 4.28, %N 19.60, %O 33.88.

Reference： [1]Current Patent Assignee: BAIN CAPITAL INC - US4160829, 1979, A

8
[ 55151-91-2 ]
[ 865671-22-3 ]
5-(6-bromo-2-chloro-8-fluoro-4-methylquinolin-3-yl)-3-methyl-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate at 110℃; for 1h;	1.1; 33 Step 1: Synthesis of Compound Int-1-1c A mixture of aniline Int-1-1a (1.52 g, 6.5 mmol), oxadiazole acid Int-1- 1b (1.12 g, 7.9 mmol) and POCl3 (10 mL) was stirred at 110 °C for 1 h. After cooling to room temperature, excess POCl3 was removed under reduced pressure. To the residue, H2O was added at 0 °C, and the mixture was stirred at 0 °C for 10 min. The precipitated crude chloroquinoline Int-1-1c was filtered, washed with H2O and dried under reduced pressure. The crude product Int-1-1c was used for the next reaction without further purification.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 80; 96-98

9
[ 55151-91-2 ]
C₂₅H₃₁F₂N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: trichlorophosphate / 1 h / 110 °C 2: trans-bis(triphenylphosphine)palladium dichloride / toluene / 80 °C 3: hydrogenchloride / water; 1,4-dioxane / 0.5 h / 20 °C 4: [RhCl₂(p-cymene)]2; sodium formate; N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide / tetrahydrofuran; water / 2.5 h / 40 °C / Inert atmosphere 5: 4-(trimethylsilyl)morpholine; diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C 6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 120 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

10
[ 55151-91-2 ]
C₂₅H₃₁F₂N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: caesium carbonate; triphenylphosphine; palladium dichloride / tetrahydrofuran; water / 24 h / 85 °C 4.1: dimethylsulfide borane complex / tetrahydrofuran / 1 h / 0 - 20 °C 4.2: 2 h / 0 - 50 °C 5.1: diethylamino-sulfur trifluoride / dichloromethane / 2.5 h / 0 - 5 °C 5.2: 2 h / 45 °C 6.1: N-ethyl-N,N-diisopropylamine; sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

11
[ 55151-91-2 ]
C₂₄H₂₇F₄N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 18 h / 120 °C 3.1: copper(l) iodide / N,N-dimethyl-formamide / 1 h / 80 °C 4.1: sulfuric acid / tetrahydrofuran; water / 1.5 h / 50 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 0.17 h / 20 °C 5.2: 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

12
[ 55151-91-2 ]
C₂₄H₂₇F₄N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1.5 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / 110 °C 3: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 18 h / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

13
[ 55151-91-2 ]
C₂₆H₂₉F₃N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / tetrahydrofuran; N,N-dimethyl-formamide / 80 °C 4.1: sulfuric acid / tetrahydrofuran; water / 2 h / 50 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 0.17 h / 20 °C 5.2: 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

14
[ 55151-91-2 ]
C₂₆H₃₂FN₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 80 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 130 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

15
[ 55151-91-2 ]
C₂₅H₃₁F₂N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 110 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

16
[ 55151-91-2 ]
C₂₆H₃₂FN₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 80 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 130 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

17
[ 55151-91-2 ]
C₂₃H₂₅FN₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / tetrahydrofuran; N,N-dimethyl-formamide / 5 h / 80 °C 4.1: sulfuric acid / tetrahydrofuran; water / 4 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 0.17 h / 20 °C 5.2: 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

18
[ 55151-91-2 ]
C₂₄H₂₅N₇O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / tetrahydrofuran; N,N-dimethyl-formamide / 5 h / 80 °C 4.1: sulfuric acid / tetrahydrofuran; water / 4 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 0.17 h / 20 °C 5.2: 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

19
[ 55151-91-2 ]
1-(6-ethyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 110 °C 3: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

20
[ 55151-91-2 ]
C₂₅H₃₁F₂N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 80 °C 2: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 125 °C 3: sulfuric acid / water / 2 h / 45 °C 4: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

21
[ 55151-91-2 ]
C₂₅H₃₂FN₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 110 °C 3: hydrogenchloride / water; acetone / 5 h / 20 °C 4: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

22
[ 55151-91-2 ]
C₂₂H₂₅ClFN₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1.5 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 110 °C 3: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

23
[ 55151-91-2 ]
C₂₃H₂₈FN₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0.08 h / 50 °C 1.2: 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4.1: acetic acid / 1,2-dichloro-ethane / 0.5 h / 20 °C 4.2: 20 °C
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere 4.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 5.1: acetic acid / 1,2-dichloro-ethane / 0.5 h / 20 °C 5.2: 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

24
[ 55151-91-2 ]
C₂₇H₃₄FN₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: palladium diacetate; caesium carbonate; catacxium A / water; toluene / 100 °C 4.1: sulfuric acid / tetrahydrofuran; water / 4 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 0.17 h / 20 °C 5.2: 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

25
[ 55151-91-2 ]
(2R,4S)-1-(6-ethyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-(tetrahydro-2H-pyran-4-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: potassium fluoride / N,N-dimethyl-formamide / 18 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

26
[ 55151-91-2 ]
(2S,4S)-1-(6-ethyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-(tetrahydro-2H-pyran-4-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: potassium fluoride / N,N-dimethyl-formamide / 18 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

27
[ 55151-91-2 ]
C₂₆H₃₂FN₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: palladium diacetate; caesium carbonate; catacxium A / water; toluene / 100 °C 4.1: sulfuric acid / tetrahydrofuran; water / 4 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 0.17 h / 20 °C 5.2: 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

28
[ 55151-91-2 ]
(2R,4R)-1-(6-chloro-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-(tetrahydro-2H-pyran-4-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 80 °C 2: potassium fluoride / dimethyl sulfoxide / 14 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

29
[ 55151-91-2 ]
(2R,4R)-1-(8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-6-(trifluoromethoxy)quinolin-2-yl)-2-methyl-N-((S)-tetrahydrofuran-3-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 18 h / 140 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

30
[ 55151-91-2 ]
4,6-dimethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-((2R,4R)-2-methyl-4-((tetrahydro-2H-pyran-4-yl)amino)piperidin-1-yl)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 80 °C 2: potassium fluoride / dimethyl sulfoxide / 14 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

31
[ 55151-91-2 ]
1-(6-cyclobutyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: palladium diacetate; caesium carbonate; catacxium A / water; toluene / 100 °C 4: sulfuric acid / tetrahydrofuran; water / 4 h / 45 °C 5: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 0.1 h / 25 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

32
[ 55151-91-2 ]
(2R,4R)-1-(6-cyclopropyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-(tetrahydro-2H-pyran-4-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 80 °C 2: potassium fluoride / dimethyl sulfoxide / 18 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

33
[ 55151-91-2 ]
(2R,4R)-1-(6-ethyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-((S)-tetrahydrofuran-3-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: potassium fluoride / N,N-dimethyl-formamide / 18 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

34
[ 55151-91-2 ]
C₂₇H₃₄FN₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: palladium diacetate; caesium carbonate; catacxium A / water; toluene / 100 °C 4: sulfuric acid / tetrahydrofuran; water / 4 h / 45 °C 5: N-ethyl-N,N-diisopropylamine; sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 0.1 h / 25 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

35
[ 55151-91-2 ]
(2R,4S)-1-(8-fluoro-6-methoxy-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-((S)-tetrahydrofuran-3-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 18 h / 125 °C 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / 1,4-dioxane / 2 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

36
[ 55151-91-2 ]
(2S,4S)-1-(8-fluoro-6-methoxy-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-((S)-tetrahydrofuran-3-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 18 h / 125 °C 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / 1,4-dioxane / 2 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

37
[ 55151-91-2 ]
(2R,4R)-1-(8-fluoro-6-(methoxy-d3)-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-((S)-tetrahydrofuran-3-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 18 h / 125 °C 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / 1,4-dioxane / 18 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

38
[ 55151-91-2 ]
(2R,4R)-1-(8-fluoro-6-isopropyl-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-((S)-tetrahydrofuran-3-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 18 h / 125 °C 3: palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; zinc dibromide / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

39
[ 55151-91-2 ]
4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-((2R,4R)-2-methyl-4-(((R)-tetrahydrofuran-3-yl)amino)piperidin-1-yl)quinoline-6,8-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 18 h / 125 °C 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / tetrahydrofuran; N,N-dimethyl-formamide / 18 h / 80 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

40
[ 55151-91-2 ]
6-ethyl-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-((2R,4R)-2-methyl-4-(((R)-tetrahydrofuran-3-yl)amino)piperidin-1-yl)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 18 h / 125 °C 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / tetrahydrofuran; N,N-dimethyl-formamide / 18 h / 80 °C 4: palladium diacetate; potassium phosphate; tricyclohexylphosphine / water; toluene / 18 h / 100 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

41
[ 55151-91-2 ]
6-ethyl-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-((2R,4R)-2-methyl-4-(((S)-tetrahydrofuran-3-yl)amino)piperidin-1-yl)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 18 h / 125 °C 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / N,N-dimethyl-formamide / 18 h / 80 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

42
[ 55151-91-2 ]
6-ethyl-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-((2R,4R)-2-methyl-4-((tetrahydro-2H-pyran-4-yl)amino)piperidin-1-yl)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 100 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 18 h / 125 °C 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / N,N-dimethyl-formamide / 18 h / 80 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

43
[ 55151-91-2 ]
(2R,4R)-1-(8-fluoro-4,6-dimethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-(tetrahydro-2H-pyran-4-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / N,N-dimethyl-formamide / 18 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

44
[ 55151-91-2 ]
(2R)-1-(8-fluoro-4,6-dimethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-((S)-tetrahydrofuran-3-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / N,N-dimethyl-formamide / 18 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

45
[ 55151-91-2 ]
(2R)-1-(8-fluoro-4,6-dimethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-2-methyl-N-((R)-tetrahydrofuran-3-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine; potassium fluoride / N,N-dimethyl-formamide / 18 h / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

46
[ 55151-91-2 ]
1-(6-chloro-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 80 °C 2: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 120 °C 3: sulfuric acid / tetrahydrofuran; water / 2 h / 40 °C 4: N-ethyl-N,N-diisopropylamine; sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

47
[ 55151-91-2 ]
1-(8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-6-(trifluoromethoxy)quinolin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: trichlorophosphate / 1 h 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: sulfuric acid / tetrahydrofuran; water / 2 h / 50 °C 4.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 0.17 h / 20 °C 4.2: 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

48
[ 55151-91-2 ]
4,6-dimethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-((2R,4R)-2-methyl-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)piperidin-1-yl)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 80 °C 2: potassium fluoride / dimethyl sulfoxide / 125 °C 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

49
[ 55151-91-2 ]
4,6-dimethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-((2R,4R)-2-methyl-4-((((R)-tetrahydrofuran-2-yl)methyl)amino)piperidin-1-yl)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 80 °C 2: potassium fluoride / dimethyl sulfoxide / 125 °C 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4: N-ethyl-N,N-diisopropylamine / acetonitrile / 80 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

50
[ 55151-91-2 ]
2-((3S,4R)-3-fluoro-4-((tetrahydro-2H-pyran-4-yl)amino)piperidin-1-yl)-4,6-dimethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 80 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

51
[ 55151-91-2 ]
(3S,4R)-1-(6-ethyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-3-methyl-N-(tetrahydro-2H-pyran-4-yl)piperidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 125 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

52
[ 55151-91-2 ]
8-(6-bromo-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

53
[ 55151-91-2 ]
C₂₃H₂₇FN₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; zinc dibromide / tetrahydrofuran / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

54
[ 55151-91-2 ]
C₂₁H₂₃FN₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; zinc dibromide / tetrahydrofuran / 20 °C 4: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

55
[ 55151-91-2 ]
C₂₄H₂₇FN₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: palladium diacetate; caesium carbonate; catacxium A / water; toluene / 100 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

56
[ 55151-91-2 ]
1-(6-cyclobutyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)piperidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: palladium diacetate; caesium carbonate; catacxium A / water; toluene / 100 °C 4: sulfuric acid / tetrahydrofuran; water / 4 h / 45 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

57
[ 55151-91-2 ]
C₂₆H₃₄FN₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; zinc dibromide / tetrahydrofuran / 20 °C 4.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 0.17 h / 20 °C 5.2: 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

58
[ 55151-91-2 ]
1-(6-bromo-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)piperidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: sulfuric acid / tetrahydrofuran; water / 3 h / 45 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

59
[ 55151-91-2 ]
8-(8-fluoro-6-methoxy-4-methyl-3-(3-methyl-1.2.4-oxadiazol-5-yl)quinolin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.08 h / 50 °C 1.2: 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.75 h / 110 °C / Microwave irradiation
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

60
[ 55151-91-2 ]
C₁₉H₁₉FN₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: trichlorophosphate / 0.08 h / 50 °C 1.2: 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere 4: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

61
[ 55151-91-2 ]
C₂₄H₃₀FN₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0.08 h / 50 °C 1.2: 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine; acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 4.2: 5 h / 20 °C
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere 4.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine; acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 5.2: 5 h / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

62
[ 55151-91-2 ]
C₂₃H₂₇FN₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: caesium carbonate; bis(η3-allyl-μ-chloropalladium(II)); di-tert-butyl (2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1‘-biphenyl]-2-yl)phosphine / toluene / 90 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

63
[ 55151-91-2 ]
C₂₁H₂₃FN₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: caesium carbonate; bis(η3-allyl-μ-chloropalladium(II)); di-tert-butyl (2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1‘-biphenyl]-2-yl)phosphine / toluene / 90 °C / Inert atmosphere 4: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

64
[ 55151-91-2 ]
C₂₃H₂₈FN₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0.08 h / 50 °C 1.2: 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4.1: acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 4.2: 5 h / 20 °C
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere 4.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 5.1: acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 5.2: 5 h / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

65
[ 55151-91-2 ]
C₂₂H₂₆FN₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0.08 h / 50 °C 1.2: 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4.1: acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 4.2: 5 h / 20 °C
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere 4.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 5.1: acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 5.2: 5 h / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

66
[ 55151-91-2 ]
C₂₄H₃₀FN₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0.08 h / 50 °C 1.2: 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4.1: acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 4.2: 5 h / 20 °C
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere 4.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 5.1: acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 5.2: 5 h / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

67
[ 55151-91-2 ]
C₂₄H₃₀FN₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0.08 h / 50 °C 1.2: 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4.1: N-ethyl-N,N-diisopropylamine; acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 4.2: 5 h / 20 °C
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere 4.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 5.1: N-ethyl-N,N-diisopropylamine; acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 5.2: 5 h / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

68
[ 55151-91-2 ]
C₂₃H₂₈FN₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0.08 h / 50 °C 1.2: 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4.1: acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 4.2: 5 h / 20 °C
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere 4.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 5.1: acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 5.2: 5 h / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

69
[ 55151-91-2 ]
C₁₉H₁₈BrIN₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

70
[ 55151-91-2 ]
6-bromo-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / tetrahydrofuran; N,N-dimethyl-formamide / 80 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

71
[ 55151-91-2 ]
C₂₂H₂₃N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / tetrahydrofuran; N,N-dimethyl-formamide / 80 °C 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 70 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

72
[ 55151-91-2 ]
C₂₀H₁₉N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / tetrahydrofuran; N,N-dimethyl-formamide / 80 °C 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 70 °C 5: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

73
[ 55151-91-2 ]
C₂₀H₂₀BrIN₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 18 h / 120 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

74
[ 55151-91-2 ]
C₂₃H₂₈FN₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0.08 h / 50 °C 1.2: 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 0.75 h / 110 °C / Microwave irradiation 3.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 4.1: acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 4.2: 5 h / 20 °C
	Multi-step reaction with 5 steps 1.1: trichlorophosphate / 1 h / 110 °C 2.1: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere 4.1: sulfuric acid / tetrahydrofuran; water / 2 h / 45 °C 5.1: acetic acid / 1,2-dichloro-ethane / 0.25 h / 20 °C 5.2: 5 h / 20 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

75
[ 55151-91-2 ]
C₂₁H₂₀BrN₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 18 h / 120 °C 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc / tetrahydrofuran; N,N-dimethyl-formamide / 18 h / 80 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

76
[ 55151-91-2 ]
8-(8-fluoro-4,6-dimethyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C
	Multi-step reaction with 3 steps 1: trichlorophosphate / 1 h / 110 °C 2: N-ethyl-N,N-diisopropylamine / ethanol / 120 °C 3: trans-bis(triphenylphosphine)palladium dichloride / 1,4-dioxane; hexane / 1 h / 60 °C

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1
[2]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1

77
[ 55151-91-2 ]
C₁₁H₁₂FNO [ No CAS ]
C₁₆H₁₃ClFN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate at 80℃; for 1h;	11 Synthesis of 42 mixture of Int-11-40 (1.0 equiv.) and Int-11-41 (1.0 equiv.) in POCl3 was heated at 80 °C for 1h. The excess POCl3 was removed under reduced pressure. The residue was quenched with ice and the mixture was stirred for 15 min. The pale brown product was collected by filtration and used in the next step without further purificaotion (53-55% yield). LCMS: (M+1) m/z = 318.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 84; 85

78
[ 55151-91-2 ]
1-(2-amino-5-methoxy-3-fluorophenyl)ethanone [ No CAS ]
5-(2-chloro-8-fluoro-6-methoxy-4-methylquinolin-3-yl)-3-methyl-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: 2-(3-methyl-1,2,4-oxadiazol-5-yl)acetic acid With trichlorophosphate at 50℃; for 0.0833333h; Stage #2: 1-(2-amino-5-methoxy-3-fluorophenyl)ethanone at 110℃; for 1h;	36 Synthesis of Int-36-14h A solution of 2-(3-methyl-1,2,4-oxadiazol-5-yl)acetic acid Int-33-14g (72 mg, 0.50 mmol) in POCl3 (1.5 mL) was stirred at 50 °C for 5 min before ketone Int-36-7 (92 mg, 0.50 mmol) was added. The mixture was heated to 110 °C for 1h. The excess POCl3 was removed under vacuum. To the residue was added sat. aq. solution of NaHCO3, and the product was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to dryness. The crude product was purified by column chromatography (hexanes/EtOAc) to give 2-chloroquinoline Int-36-14h as a yellow solid (69 mg, 45% yield). LCMS: (M+1) m/z = 307, 309.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 100-102

79
[ 55151-91-2 ]
C₇H₅BrINO [ No CAS ]
C₁₂H₆BrClIN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate at 110℃; for 1h;	90 Synthesis of Int-90-14 A mixture of aldehyde Int-90-11 (4.50 g, 13.8 mmol), oxadiazole acid Int-90-12 (2.36 g, 16.6 mmol) and POCl3 (14 mL) was stirred at 110 °C for 1 h. After cooling to room temperature, excess POCl3 was removed under reduced pressure. To this residue, H2O was added at 0 °C. The mixture was stirred at 0 °C for 10 min. The crude chloride Int-90-13 was filtered, washed with H2O and dried under reduced pressure. To a suspension of Int-90-13 in EtOH (70 mL) were added 1,4-dioxa-8- azaspiro[4,5]decane (3.5 mL, 27.6 mmol) and DIPEA (4.8 mL, 27.6 mmol) at room temperature. The mixture was then heated at 120 °C overnight. After cooling to room temperature, the mixture was concentrated and purified by column chromatography (hexanes/EtOAc gradient) to give quinoline Int-90-14 as yellow oil (2.61 g, 34% yield over two steps).

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 120; 121

80
[ 55151-91-2 ]
2-amino-5-bromo-3-iodoacetophenone [ No CAS ]
C₁₃H₈BrClIN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate at 110℃; for 1h;	91 Synthesis of Int-91-21 A mixture of ketone Int-91-19 (5.02 g, 14.8 mmol), oxadiazole acid Int- 91-12 (2.52 g, 17.7 mmol) and POCl3 (15 mL) was stirred at 110 °C for 1 h. After cooling to room temperature, excess POCl3 was removed under reduced pressure. To this residue, H2O was added at 0 °C. The mixture was stirred at 0 °C for 10 min. The crude chloride Int-91-20 was filtered, washed with H2O and dried under reduced pressure. To a suspension of Int-91-20 in EtOH (74 mL) were added 1,4-dioxa-8- azaspiro[4,5]decane (3.8 mL, 29.6 mmol) and DIPEA (5.2 mL, 29.6 mmol) at room temperature. The mixture was then heated at 120 °C overnight. After cooling to room temperature, the mixture was concentrated and purified by column chromatography (hexanes/EtOAc gradient) to give quinoline Int-91-21 as yellow oil (2.54 g, 30% yield over two steps).

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 123; 124

81
[ 55151-91-2 ]
[ 935292-91-4 ]
C₁₃H₈ClFIN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate at 110℃; for 1h;	103 Synthesis of Int-103-16 A mixture of Int-103-15 (2.20 g, 7.9 mmol), oxadiazole acid (1.34 g, 9.5 mmol) and POCl3 (10 mL) was stirred at 110 °C for 1 h. After cooling to room temperature, excess POCl3 was removed in vacuo. The residue was partitioned between H2O and CH2Cl2. The organic layer was separated, washed with sat. aq. NaHCO3, dried over Na2SO4 and concentrated. Residue Int-103-16 was used for the next reaction without further purification.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 143; 145

82
[ 55151-91-2 ]
C₉H₇F₄NO [ No CAS ]
C₁₄H₈ClF₄N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate at 110℃; for 1.5h;	108 Synthesis of Int-108-33 and Int-108-34 A mixture of aldehyde Int-108-32 (1.0 equiv.), acid Int-108-9 (1.0 equiv.) and POCl3 was stirred at 110 °C for 1.5 h. The excess POCl3 was removed under reduced pressure. The residue was resuspended in a sat. aq. NaHCO3 solution and extracted with EtOAc (2X). The combined organic layers were dried over Na2SO4 and concentrated to dryness. The crude product was purified by column chromatography (Hexanes/EtOAc) to yield quinoline Int-108-34 as a white solid (15-17% yield). LCMS: (M+1) m/z = 346.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 147; 149

83
[ 55151-91-2 ]
C₁₀H₉F₃INO [ No CAS ]
C₁₅H₁₀ClF₃IN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate at 110℃; for 1h;	111 Synthesis of Int-111-5 mixture of Int-111-4 (1.17 g, 3.41 mmol), oxadiazole acid (0.58 g, 4.09 mmol) and POCl3 (7 mL) was stirred at 110 °C for 1 h. After cooling to room temperature, excess POCl3 was removed under the reduced pressure. To the residue, H2O was added at 0 °C, and the mixture was stirred at 0 °C for 10 min. The precipitated crude chloroquinoline 5 was filtered, washed with H2O and dried under the reduced pressure. The crude product Int-111-5 was used for the next reaction without further purification.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 151-153

84
[ 55151-91-2 ]
C₉H₁₀FNO [ No CAS ]
C₁₄H₁₁ClFN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With trichlorophosphate at 110℃; for 1h;	118 Synthesis of Int-118-7 A mixture of Int-118-6 (371 mg, 2.22 mmol), oxadiazole acid (380 mg, 2.67 mmol) and POCl3 (4.5 mL) was stirred at 110 °C for 1 h. After cooling to room temperature, excess POCl3 was removed under reduced pressure. The residue was partitioned between CH2Cl2 and H2O. The organic layer was separated, washed with sat. aq. NaHCO3, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (Hexanes/EtOAc gradient) to give compound Int-118-7 as a pale brown solid (0.25 g, 39% yield). LCMS: (M+1) m/z = 292.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 155; 157

85
[ 55151-91-2 ]
C₈H₅ClN₂O [ No CAS ]
C₁₃H₆Cl₂N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With trichlorophosphate at 110℃; for 1h;	138 Synthesis of Int-138-6 A mixture of Int-138-5 (180 mg, 1.00 mmol), oxadiazole acid (175 mg, 1.23 mmol) and POCl3 (3 mL) was stirred at 110 °C for 1 h. After cooling to room temperature, excess POCl3 was removed under the reduced pressure. To the residue, H2O was added at 0 °C. The mixture was partitioned between EtOAc and brine. The aqueous layer was separated and extracted with EtOAc (×2). The combined organic layers were dried over Na2SO4 and concentrated to dryness. Product Int-138-6 as a brown solid was used for the next reaction without further purification (281 mg, 92% yield).

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 161; 162

86
[ 55151-91-2 ]
C₇H₅FINO [ No CAS ]
C₁₂H₆ClFIN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate at 110℃; for 1h;	139 Synthesis of Int-139-Int-139-30 A mixture of aldehyde Int-139-Int-139-28 (5.74 g, 21.6 mmol), oxadiazole acid Int-139-Int-139-12 (3.69 g, 26.0 mmol) and POCl3 (22 mL) was stirred at 110 °C for 1 h. After cooling to room temperature, excess POCl3 was removed under reduced pressure. To this residue, H2O was added at 0 °C. and the mixture was stirred at 0 °C for 10 min. The crude chloride 29 was filtered, washed with H2O and dried under reduced pressure. To a suspension of 29 in EtOH (100 mL) were added 1,4- dioxa-8-azaspiro[4,5]decane (5.5 mL, 43.2 mmol) and DIPEA (7.5 mL, 43.2 mmol) at room temperature. The mixture was then heated at 120 °C overnight. After cooling to room temperature, the mixture was concentrated and purified by column chromatography (hexanes/EtOAc gradient) to give quinoline Int-139-Int-139-30 as yellow oil (2.50 g, 23% yield over two steps).

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 163; 164

87
[ 55151-91-2 ]
C₇H₅I₂NO [ No CAS ]
C₁₂H₆ClI₂N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate at 110℃; for 1h;	140 Synthesis of Int-140-38 A mixture of aldehyde Int-140-36 (4.81 g, 12.9 mmol), oxadiazole acid 12 (3.69 g, 15.5 mmol) and POCl3 (13 mL) was stirred at 110 °C for 1 h. After cooling to room temperature, excess POCl3 was removed under reduced pressure. To this residue, H2O was added at 0 °C. The mixture was stirred at 0 °C for 10 min. The crude chloride Int-140-37 was filtered, washed with H2O and dried under reduced pressure. To a suspension of Int-140-37 in EtOH (65 mL) were added 1,4-dioxa-8- azaspiro[4,5]decane (3.3 mL, 25.8 mmol) and DIPEA (4.5 mL, 25.8 mmol) at room temperature. The mixture was then heated at 120 °C overnight. After cooling to room temperature, the mixture was concentrated and purified by column chromatography (hexanes/EtOAc gradient) to give quinoline Int-140-38 as yellow oil (1.56 g, 20% yield over two steps).

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; BLACKTHORN THERAPEUTICS INC - WO2018/170492, 2018, A1 Location in patent: Page/Page column 165; 166

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	55151-91-2	MDL No. :	MFCD13705349
Formula :	C₅H₆N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SPLXTCXODDVKKW-UHFFFAOYSA-N
M.W :	142.11	Pubchem ID :	21313018
Synonyms :

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.4
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	30.81
TPSA :	76.22 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.14 cm/s

Log Po/w (iLOGP) :	0.93
Log Po/w (XLOGP3) :	0.04
Log Po/w (WLOGP) :	0.01
Log Po/w (MLOGP) :	-1.09
Log Po/w (SILICOS-IT) :	0.51
Consensus Log Po/w :	0.08

[ CAS No. 55151-91-2 ] {[proInfo.proName]}

Quality Control of [ 55151-91-2 ]

Related Doc. of [ 55151-91-2 ]

Product Details of [ 55151-91-2 ]

Calculated chemistry of [ 55151-91-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 55151-91-2 ]

Application In Synthesis of [ 55151-91-2 ]

[ 55151-91-2 ] Synthesis Path-Downstream 1~87

Related Functional Groups of
[ 55151-91-2 ]

Carboxylic Acids

Related Parent Nucleus of
[ 55151-91-2 ]

Oxadiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Log S (ESOL) :	-0.98
Solubility :	14.7 mg/ml ; 0.104 mol/l
Class :	Very soluble
Log S (Ali) :	-1.19
Solubility :	9.11 mg/ml ; 0.0641 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.01
Solubility :	14.0 mg/ml ; 0.0984 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.56

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:	N/A
Hazard Statements:	H302-H312-H332	Packing Group:	N/A
GHS Pictogram:

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

[ CAS No. 55151-91-2 ] {[proInfo.proName]}

Quality Control of [ 55151-91-2 ]

Related Doc. of [ 55151-91-2 ]

Product Details of [ 55151-91-2 ]

Calculated chemistry of [ 55151-91-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 55151-91-2 ]

Application In Synthesis of [ 55151-91-2 ]

[ 55151-91-2 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 55151-91-2 ]

Carboxylic Acids

Related Parent Nucleus of [ 55151-91-2 ]

Oxadiazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 55151-91-2 ]

Related Parent Nucleus of
[ 55151-91-2 ]