5932-30-9|Ethyl 5-phenyl-1H-pyrazole-3-carboxylate| Ambeed

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Quality Control of [ 5932-30-9 ] Purity: 97% SDS Specification

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Product Details of [ 5932-30-9 ]

CAS No. :	5932-30-9
Formula :	C₁₂H₁₂N₂O₂
M.W :	216.24
SMILES Code :	O=C(C1=NNC(C2=CC=CC=C2)=C1)OCC
MDL No. :	MFCD02130942
InChI Key :	AZZHJDRWBMQEKD-UHFFFAOYSA-N
Pubchem ID :	138628

Safety of [ 5932-30-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 5932-30-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	11
Fraction Csp3	0.17
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	60.11
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.98 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.09
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.43
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.25
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.61
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.74
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.22

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.96
Solubility	0.239 mg/ml ; 0.00111 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.23
Solubility	0.128 mg/ml ; 0.000592 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.24
Solubility	0.0124 mg/ml ; 0.0000574 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.89 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.37

Application In Synthesis of [ 5932-30-9 ]

* 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 [ 5932-30-9 ]

[ 5932-30-9 ] Synthesis Path-Downstream 1~35

1
[ 623-73-4 ]
[ 536-74-3 ]
[ 5932-30-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-diaza-bicyclo[2.2.2]octane; at 20℃; for 6h;	To a mixture of phenyl acetylene 1 (0.1 g, 1 mmol) and ethyldiazoacetate 2 (0.114 g) was added DABCO (1,4-diazabicyclo[2.2.2]octane) (0.011 g, 0.1 mmol) and stirred for 6 h at ambienttemperature. Upon completion of the reaction which was monitoredby TLC, the crude reaction product was purified by passingthrough Silica gel using 20% ethyl acetate in pet. ether to affordcompound 3.

References: [1]Green Chemistry,2009,vol. 11,p. 156 - 159.
[2]Tetrahedron Letters,2008,vol. 49,p. 6768 - 6772.
[3]Chemische Berichte,1902,vol. 35,p. 36.
[4]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 6209 - 6219.
[5]Bioorganic Chemistry,2022,vol. 124.
[6]Bioorganic Chemistry,2022,vol. 124.

2
[ 5932-30-9 ]
[ 108-24-7 ]
ethyl 1-acetyl-5-phenyl-1H-pyrazole-3-carboxylate [ No CAS ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1934,vol. <2> 139,p. 69.

3
[ 5932-30-9 ]
[ 79-22-1 ]
5-phenyl-pyrazole-1,3-dicarboxylic acid-3-ethyl ester-1-methyl ester [ No CAS ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1934,vol. <2> 139,p. 69.

4
[ 5932-30-9 ]
[ 179057-19-3 ]

References: [1]Journal of Organic Chemistry,1954,vol. 19,p. 1428,1431.
[2]Bioorganic Chemistry,2020,vol. 102.

5
[ 6296-54-4 ]
[ 5932-30-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrazine hydrate; acetic acid; In ethanol; at 20℃; for 5h;	To a solution of compound 22 (l. lg, 5 mmol) and AcOH (0.360 g, 5.00 mmol) in 20 ml EtOH was added 80% hydrazine hydrate (0.316 g, 5.05 mmol). After stirred at rt for 5h, the mixture was diluted with water,' then EtOH was removed under reduced pressure, and aqueous solution was made alkaline by saturated aqueous solution of NaHC03 then extracted with ethyl acetate, dried by anhydrous Na2S04, concentrated to afford compound 23 (1.08 g, 99% yield).LCMS m/z=217 [M+H] + LC/MS informationColumn: Xbridge C 18 (3.5μιη 4.6x50mm)Flow rate: 1.8 mL/minUV detection wavelength: 254nmMobile phase: [A] is 0.05% TFA-containing aqueoous solution, and [B] is 0.05% TFA- containing acetonitrile solutionFrom 0 to 1.5 minutes, . the percentage of [B] in the mobile phase was gradually increased from 5% to 100%. Thereafter a solution of 100% of [B] was used as the mobile phase.retention time= 1.21 minutes.
95.6%	With hydrazine hydrate; In ethanol; at 20℃; for 3h;Reflux;	The above obtained intermediate 2-1 (9.3 g, 0.042 mol) was added into a round-bottom flask charged with 50 mL of ethanol, followed by addition of hydrazine hydrate (2.1 g, 0.042 mol) dropwise under stirring at room temperature. After the completion of the addition, the mixture was refluxed for 3 hours and then cooled to room temperature. The ethanol was evaporated, and 10 mL of water was added. The mixture was extracted with ethyl acetate (3×20 mL), and the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized with ethyl acetate/petroleum ether (1:5) to give 8.68 g of intermediate 3-1 with a yield of 95.6%.
67%	With hydrazine; In ethanol; for 3h;Heating / reflux;	Reference Example 23 Ethyl 5-phenyl-1H-pyrazole-3-carboxylate To a solution of ethyl 2,4-dioxo-4-phenylbutanoate (16.0 g) in ethanol (150 mL) was added hydrazine monohydrate (4.0 mL), and the mixture was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from diisopropyl ether to give the title compound as a pale-brown solid (yield 12.0 g, 67%). 1H-NMR (CDCl3) δ: 1.41 (3H, t, J=7.4 Hz), 4.41 (2H, q, J=7.4 Hz), 4.80-6.50 (1H, brs), 7.12 (1H, s), 7.30-7.50 (3H, m), 7.79 (2H, d, J=7.9 Hz).

40.7%	With hydrazine hydrate; In ethanol; at 20℃; for 5h;	To a solution of REX-P-INT-2 (8.6 g, 39.1 mmol) in EtOH (50 mL) was added hydrazine hydrate (2.3 g, 46.9 mmol). The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into aqueous solution of sodium bicarbonate (100 mL), extracted with EtOAc, washed with brine, dried with anhydrous Na2SO4, filtered and concentrated to give the crude product. The crude product was purified by silica gel chromatography eluted to give product 1-3 (3.4 g, 40.7%). MS m/z [ESI]: 217.1 [M+1].
	With hydrazine hydrate; triethylamine; In ethanol; at 20℃; for 1h;	Preparation 149Ethyl 5-phenyl-1 H-pyrazole- -carboxylateTo a solution of Preparation 28 in ethanol (350 mL) hydrazine hydrate (2.51 g, 16.72 mmol) in ethanol (70 mL) and triethylamine (2.33 mL, 16.72 mmol) were added and mixture stirred at room temperature for 1 h. Solvent was removed and crude used for next reaction withouth further purification.LRMS: m/z 217 (M+1 )+ Retention time: 5.77 min (Method B)
	With hydrazine hydrate; triethylamine; In ethanol; at 20℃; for 1h;	To a solution of Preparation 28 in ethanol (350 mL) hydrazine hydrate (2.51 g, 16.72 mmol) in ethanol (70 mL) and triethylamine (2.33 mL, 16.72 mmol) were added and mixture stirred at room temperature for 1 h. Solvent was removed and crude used for next reaction withouth further purification.LRMS: m/z 217 (M+1)+Retention time: 5.77 min (Method B)
750 mg	With hydrazine hydro-chloride; In ethanol; for 2h;Reflux;	383 mg (16.7 mmol) of sodium metal was added in portions to 15 mL of absolute ethanol.After stirring at room temperature until dissolved, diethyl oxalate (1.28 g, 8.75 mmol) was added.After 1 g (8.33 mmol) of acetophenone was dissolved in 15 mL of absolute ethanol,Add to the fresh sodium ethoxide solution under ice bath, and return to room temperature after the addition.After stirring for 6 h, 15 mL of 15% dilute hydrochloric acid was added for acidification, followed by rotary evaporation to remove most of the ethanol.Dilute with 10 mL of water and extract three times with 100 mL of ethyl acetate.The organic phases were combined and dried over anhydrous sodium sulfate.The ethyl acetate in which the product is dissolved is directly dried to obtain a crude intermediate.Re-dissolved by adding 15 mL of absolute ethanol, followed by the addition of hydrazine hydrochloride (1.31 g, 12.50 mmol) and warming to reflux.After reacting for 2 hours, it was cooled to room temperature, and 40 mL of water was added to the reaction mixture, and the mixture was extracted three times with 100 mL of ethyl acetate.The organic phases were combined and dried over anhydrous sodium sulfate.Purification by column chromatography (petroleum ether: ethyl acetate = 4: 1) to give a yellow solid 750mg,The yield is 41.7%.

References: [1]Patent: WO2012/144661,2012,A1 .Location in patent: Page/Page column 80; 81.
[2]Patent: US2020/399248,2020,A1 .Location in patent: Paragraph 0156; 0158.
[3]Patent: EP2005957,2008,A1 .Location in patent: Page/Page column 55.
[4]Patent: US2018/271846,2018,A1 .Location in patent: Paragraph 0101; 0114; 0115.
[5]Chemische Berichte,1904,vol. 37,p. 2208.
[6]Chemische Berichte,1904,vol. 37,p. 2208.
[7]Journal of Medicinal Chemistry,2003,vol. 46,p. 3945 - 3951.
[8]Patent: WO2011/144338,2011,A1 .Location in patent: Page/Page column 86.
[9]Patent: EP2390252,2011,A1 .Location in patent: Paragraph 0415; 0416.
[10]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4177 - 4184.
[11]Patent: CN110105286,2019,A .Location in patent: Paragraph 0039-0042.
[12]Bioorganic and medicinal chemistry letters,2020,vol. 30.

6
[ 5071-61-4 ]
[ 5932-30-9 ]

References: [1]Gazzetta Chimica Italiana,1940,vol. 70,p. 240,244.

7
[ 141-52-6 ]
[ 94274-67-6 ]
[ 5932-30-9 ]
[ 94274-44-9 ]
[ 94274-45-0 ]

References: [1]Liebigs Annalen der Chemie,1984,p. 1641 - 1652.

8
[ 126580-12-9 ]
[ 5932-30-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With α,α,α-trifluorotoluene; for 0.166667h;Reflux;	General procedure: A solution of vinyldiazo compound (1.0 eq) in benzotrifluoride (1.2 M) was heated to reflux until complete consumption of the vinyldiazo compound (<10 min). Silica gel was then added and the solvent evaporated. The product was purified by column chromatography (50 - 70% v/v% ethyl acetate/petrol ether) and isolated as off-white solid.

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 4144 - 4153.
[2]Synlett,2020,vol. 31,p. 1158 - 1162.

9
[ 141-52-6 ]
[ 94274-67-6 ]
[ 75-64-9 ]
[ 5932-30-9 ]
[ 94274-44-9 ]
[ 94274-45-0 ]

References: [1]Liebigs Annalen der Chemie,1984,p. 1641 - 1652.

10
[ 5932-30-9 ]
3-ethoycarbonyl-4-bromo-5-phenylpyrazole [ No CAS ]

References: [1]Heterocycles,1999,vol. 50,p. 227 - 242.

12
[ 49783-72-4 ]
[ 5932-30-9 ]
2-(3-methyl-isoxazole-5-carbonyl)-5-phenyl-2<i>H</i>-pyrazole-3-carboxylic acid ethyl ester [ No CAS ]
1-(3-methyl-isoxazole-5-carbonyl)-5-phenyl-1<i>H</i>-pyrazole-3-carboxylic acid ethyl ester [ No CAS ]

References: [1]Synthetic Communications,2002,vol. 32,p. 425 - 433.

13
[ 5932-30-9 ]
[ 5071-61-4 ]

Yield	Reaction Conditions	Operation in experiment
80.4%	With sodium hydroxide; In methanol; at 20℃; for 2h;	To a solution of 1-3 (3.4 g, 15.9 mmol) in MeOH (40 mL) was added NaOH (140 mL, 4M). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure to remove MeOH. The aqueous phase was acidified with aqueous HCl (1 M) till pH=3 and the mixture was extracted with EtOAc, dried with anhydrous Na2SO4, filtered and concentrated to give the crude product. The crude product was purified by silica gel chromatography eluted to give product 1-4 (2.4 g, 80.4%). MS m/z [ESI]: 189.1 [M+1].
	With sodium hydroxide; In methanol; at 20℃; for 0.5h;	A solution of the ester 3 (0.1 g, 0.46 mmol) in MeOH (4 mL) was treated with 4 N NaOH (4 mL) and stirred at rt for 30 min. Later methanol was removed in vacuo and adjusted to pH 2-3 with aq1 N HCl and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and evaporated to get acid 4.

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3945 - 3951.
[2]Patent: US2018/271846,2018,A1 .Location in patent: Paragraph 0101; 0116; 0117.
[3]New Journal of Chemistry,2011,vol. 35,p. 865 - 875.
[4]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 6209 - 6219.
[5]Bioorganic Chemistry,2022,vol. 124.
[6]Bioorganic Chemistry,2022,vol. 124.

14
[ 25445-76-5 ]
[ 95-92-1 ]
[ 5932-30-9 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 3591 - 3593.
[2]Tetrahedron,2008,vol. 64,p. 2207 - 2215.

15
[ 98-86-2 ]
[ 5932-30-9 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3945 - 3951.
[2]Patent: WO2011/144338,2011,A1 .
[3]Patent: EP2390252,2011,A1 .
[4]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4177 - 4184.
[5]Chinese Journal of Chemistry,2014,vol. 32,p. 179 - 190.
[6]Patent: US2018/271846,2018,A1 .
[7]Patent: CN110105286,2019,A .
[8]ACS Medicinal Chemistry Letters,2020,vol. 11,p. 605 - 610.
[9]Bioorganic and medicinal chemistry letters,2020,vol. 30.
[10]Patent: US2020/399248,2020,A1 .

16
[ 122-78-1 ]
[ 5932-30-9 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 4144 - 4153.

17
[ 126580-09-4 ]
[ 5932-30-9 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 4144 - 4153.

18
[ 14441-90-8 ]
[ 5932-30-9 ]

References: [1]Gazzetta Chimica Italiana,1940,vol. 70,p. 240,244.

19
[ 5932-30-9 ]
[ 98-59-9 ]
[ 952191-72-9 ]

Yield	Reaction Conditions	Operation in experiment
20%		Reference Example 24 Ethyl 1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrazole-3-carboxylate Sodium hydride (60% in oil, 612 mg) was washed with hexane, suspended in N,N-dimethylformamide solution (5 mL), and a solution of <strong>[5932-30-9]ethyl 5-phenyl-1H-pyrazole-3-carboxylate</strong> (3.0 g) in N,N-dimethylformamide (10 mL) was added dropwise. After the completion of the dropwise addition, the reaction mixture was stirred at room temperature for 30 min, and added dropwise to an ice-cooled solution of p-toluenesulfonyl chloride (3.16 g) in N,N-dimethylformamide (10 mL). After the completion of the dropwise addition, the reaction mixture was stirred at room temperature for 1 hr, and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→1:1) to give the title compound as a colorless solid (yield 1.037 g, 20%). 1H-NMR (CDCl3) δ: 1.42 (3H, t, J=7.4 Hz), 2.43 (3H, s), 4.43 (2H, q, J=7.4 Hz), 7.03 (1H, s), 7.30-7.50 (5H, m), 7.75-7.85 (2H, m), 8.07 (2H, d, J=8.4 Hz).

References: [1]Patent: EP2005957,2008,A1 .Location in patent: Page/Page column 55.

20
[ 98-86-2 ]
[ 95-92-1 ]
[ 5932-30-9 ]

References: [1]New Journal of Chemistry,2011,vol. 35,p. 865 - 875.
[2]Bioorganic Chemistry,2020,vol. 102.

21
[ 7357-67-7 ]
[ 5932-30-9 ]
[ 1403947-53-4 ]
[ 1403947-52-3 ]

Yield	Reaction Conditions	Operation in experiment
8.7%; 55%	With potassium carbonate; In acetonitrile; for 8h;Reflux;	To a solution of compound 23 (l.08g, 5.00 mmol) and compound 25 (981 mg, 6.00 mmol) in 50 ml acetonitrile was added K2CO3 (1.24 g, 9.00 mmol) and heated to reflux for 8 hours. After cooled to rt, filtered off, the filtrate was concentrated and the residue was purified by silica-gel column chromatography to afford compound 24a (950 mg, 55% yield) and compound 24b (150 mg, 8.7% yield).(compound 24a)LCMS m/z=344 [M+H]+ LC/MS informationColumn: Xbridge C18 (3.5pm 4.6x50mm)Flow rate: 1.8 mL/min UV detection wavelength: 254nmMobile phase'- [A] is 0.05% TFA-containing aqueoous solution, and [B] is 0.05% TFA- containing acetonitrile solutionFrom 0 to 1.5 minutes, the percentage of [B] in the mobile phase was gradually increased from 5% to 100%. Thereafter a solution of 100% of [B] was used as the mobile phase.retention time= 1.41 minutes.(compound 24b)LCMS m/z=344 [M+H]+ LC/MS informationColumn: Xbridge C18 (3.5μϖι 4.6x50mm)Flow rate: 1.8 mL/minUV detection wavelength: 254nmMobile phase: [A] is 0.05% TFA-containing aqueoous solution, and [B] is 0.05% TFA- containing acetonitrile solutionFrom 0 to 1.5 minutes, the percentage of [B] in the mobile phase was gradually increased from 5% to 100%.. Thereafter a solution of 100% of [B] was used as the mobile phase.retention time= 1.50 minutes

References: [1]Patent: WO2012/144661,2012,A1 .Location in patent: Page/Page column 81; 82.

22
[ 5932-30-9 ]
[ 1403947-55-6 ]

References: [1]Patent: WO2012/144661,2012,A1 .

23
[ 5932-30-9 ]
[ 1403946-40-6 ]

References: [1]Patent: WO2012/144661,2012,A1 .

24
[ 5932-30-9 ]
[ 141-43-5 ]
[ 1186640-10-7 ]