145091-87-8|5-Methyl-1H-pyrazol-3-ol| Ambeed

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Quality Control of [ 145091-87-8 ] Purity: 97% SDS Specification

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Product Details of [ 145091-87-8 ]

CAS No. :	145091-87-8
Formula :	C₄H₆N₂O
M.W :	98.10
SMILES Code :	OC1=NNC(C)=C1
MDL No. :	MFCD00129672

Safety of [ 145091-87-8 ]

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

Computational Chemistry of [ 145091-87-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	7
Num. arom. heavy atoms	5
Fraction Csp3	0.25
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	25.58
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	48.91 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.74
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	0.59
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.42
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.	-0.27
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	1.03
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.5

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.35
Solubility	4.4 mg/ml ; 0.0448 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.19
Solubility	6.33 mg/ml ; 0.0645 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-0.96
Solubility	10.6 mg/ml ; 0.108 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	No
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.	-6.48 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	2.0
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)	1.55

Application In Synthesis of [ 145091-87-8 ]

* 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 [ 145091-87-8 ]

[ 145091-87-8 ] Synthesis Path-Downstream 1~35

1
[ 15424-14-3 ]
[ 145091-87-8 ]
[ 81402-55-3 ]

References: [1]Chemistry Letters,1982,p. 119 - 122.
[2]Journal of the Chemical Society. Perkin transactions I,1982,p. 2663 - 2666.

2
[ 145091-87-8 ]
[ 36590-52-0 ]
[ 128670-96-2 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1990,vol. 29,p. 381 - 386.

3
[ 145091-87-8 ]
[ 18211-68-2 ]

References: [1]Chemistry of Heterocyclic Compounds,1998,vol. 34,p. 623 - 624.

4
[ 79-37-8 ]
[ 145091-87-8 ]
1,2-bis-(5-hydroxy-3-methyl-pyrazol-1-yl)-ethane-1,2-dione [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2006,vol. 45,p. 2485 - 2490.

5
[ 141-97-9 ]
[ 145091-87-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrazine monohydrate; In methanol; for 4h;Reflux;	In a 50 mL single-mouth bottle, hydrazine hydrate (0.75 mL, 15.4 mmol) was added dropwise to a solution of ethyl acetoacetate (2.0 mL, 15.4 mmol) in methanol (15 mL).Heat and reflux for 4 h. After TLC detection, the starting material was completely reacted, and the methanol was spun dry to obtain a pale yellow solid, which was directly taken to the next step. Yield 100%,
98%	With hydrazine hydrate monohydrate; In methanol; for 2h;Reflux;	To a suspension of hydrazine hydrate (2.6 g, 20 mmol) in methanol (5 mL), 3-keto-ethyl butanoate (1.0 g, 20 mmol) was added. The reaction mixture was then refluxed for 2 h. The reaction solvent was evaporated under vacuum to afford white solid product 42 (1.92 g, 98%); 1H NMR (CDCl3) δ 2.08 (s, 3H), 5.20 (s, 1H), 10.07 (br s, 1H).
95%	With hydrazine hydrate monohydrate; In water monomer; at 20℃; for 0.166667h;Green chemistry;	General procedure: A mixture of 0.005 g of Fe3O4(at)CeO2 as catalyst, hydrazine 2a-2c or hydrazide 4 (1.0 mmol), and β-dicarbonyl compound 1a-1c (1 mmol) in water (2 mL) was stirred at room temperature for a time indicated in Table 3. The progress of the reaction was monitored by TLC on Polygram SILG/UV 254 plates. After completion of the reaction, the catalyst was separated using an external magnet and washed several times with ethanol and deionized water for subsequent use. The product was extracted with ethyl acetate (2×10 mL), the extract was dried over Na2SO4 and evaporated, and the residue was purified by flash column chromatography (EtOAc-n-hexane, 1 : 20).

94%	With acetic acid; hydrazine; In methanol; at 0 - 20℃; for 1h;Heating / reflux;	PREPARATION 14Preparation of 3-methyl-4-phenyl-1H-pyrazol-5-ol; To a cooled (0 0C) solution of ethyl acetoacetate (2.55 mL, 20.00 mmol) in anhydrous methanol (40 mL) was added dropwise hydrazine monohydrate (0.97 mL, 20.00 mmol). The reaction mixture was allowed to warm to ambient temperature and was then heated at reflux for 1 h. The reaction mixture was cooled to ambient temperature, concentrated in vacuo and dried under high vacuum to afford 3-methyl-4- phenyl-1H-pyrazol-5-ol as a colorless solid in 94% yield (1.85 g): 1H NMR (300 MHz, <n="69"/>DMSO-d6) δ 10.27 (br s, 2H), 5.21 (s, 1 H), 2.08 (s, 3H); 13C NMR (75 MHz, DMSO-Cf6) δ 161.0, 139.3, 88.9, 11.2; MS (ES+) m/z 99.1 (M + 1 ).
92%	With hydrazine; In water monomer; at 20℃; for 0.166667h;Green chemistry;Catalytic behavior;	General procedure: To a mixture of dicarbonyl compounds (1.0 mmol) and hydrazines/hydrazides (1.0 mmol) Fe3O4(at)SiO2(at)PDETSA MNPs (0.005 g) was added in water (2 mL). The mixture was stirred for the appropriate time at rt, as shown in Tables 3, 4 and 5. Completion of the reaction was indicated by TLC monitoring. After completion of the reaction, Fe3O4(at)SiO2(at)PDETSA MNPs were separated by external magnet. Then, the product was extracted with ethyl acetate (2 x 10 mL). The organic layer was dried (Na2SO4) and evaporated, and the crude product was purified by flash column chromatography (ethyl acetate/n-hexane, 1:20) to provide the pure product.
1.92 g	With hydrazine hydrate monohydrate; In methanol; for 2h;Reflux;	To a suspension of hydrazine hydrate (2.6 g) in methanol (5 mL) ethyl-3-oxobutanoate (1.0 g) was added. The reaction mixture was then refluxed for 2h. The reaction solvent was evaporated under vacuum to afford product 42.
17 g	With hydrazine hydrate monohydrate; In toluene;Reflux;	20 g of ethyl acetoacetate was added to 130 ml of toluene,Add 26g hydrazine hydrate, reflux overnight, concentrated and then add ethyl acetate and water,Dispensing,Dry and concentrated, And the residue was separated on column to give 17 g of 3-methylpyrazol-5-ol.
22 g	With hydrazine monohydrate; In toluene;	30 g of ethyl acetoacetate was added to 190 ml of toluene, 39 g of hydrazine hydrate was added, the mixture was stirred overnight and concentrated. Ethyl acetate and water were added thereto,Separation, drying, concentration, the residue was isolated on the column 22g 3-methylpyrazol-5-ol.
22 g	With hydrazine hydrate monohydrate; In toluene;Reflux;	Put 30gEthyl acetoacetate was added to 190 ml of toluene, 39 g of hydrazine hydrate was added,The mixture was refluxed with stirring overnight, concentrated and then added with ethyl acetate and water. The layers were separated, dried and concentrated. The residue was separated on the column to give 22 g of 3-methylpyrazol-5-ol.
22 g	With hydrazine hydrate monohydrate; In toluene;Reflux;	Add 30 g of ethyl acetoacetate to 190 ml of toluene, add 39 g of hydrazine hydrate, stir and reflux overnight, concentrate and then add ethyl acetate and water, separate, dry and concentrate. The residue is separated on the column to obtain 22 g of 3-methylpyrazole -5-ol.
17 g	With hydrazine hydrate monohydrate; In toluene;Reflux;	20 g of ethyl acetoacetate was added to 130 ml of toluene, 26 g of hydrazine hydrate was added, and the mixture was stirred under reflux overnight, concentrated, and then ethyl acetate and water were added, and the mixture was separated, dried and concentrated.The residue was separated on a column to give 17 g of 3-methylpyrazol-5-ol.
	With hydrazine hydrate monohydrate; for 0.0833333h;	General procedure: In 25 ml round bottom flask, ethyl acetoacetate 1 (0.13 ml, 1.1 mmol) and hydrazinehydrate 2 (0.05 ml, 1.1 mmol) were charged and kept for 5 min to allow generation of 5-hydroxy-3-methyl-1H-pyrazole 7. Then, 10 ml water, Meglumine (0.04 gm, 20 mol %),and malononitrile 4 (0.06 ml,1 mmol) were added and stirred for 5 min followed by theaddition of 5-aryldiazenyl salicylaldehyde(s) 3 (1 mmol). The resultant mixture wasstirred at room temperature for the time specified in Table 2. The progress of the reactionwas monitored by TLC. After completion of the reaction, the reaction mixture wasfiltered and washed with 2ml hot water to furnish the corresponding product 2-amino-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-6-aryldiazenyl-4H-chromene-3-carbonitriles 5.
	With p-dodecylbenzenesulfonic acid sodium salt; hydrazine hydrate monohydrate; In ethanol; water monomer;Reflux;	To an equimolar mixture of two reagents ethyl acetoacetate 1 (5 mmol) and hydrazine hydrate 2 (5 mmol) in the presence of SDBS as a catalyst (x mol%) was added EtOH -H2O (1:1, 5 mL) in a 250 mL round-bottom tricol flask equipped with a condenser and heated in a refluxing sand bath under stirring. After the for- mation of the pyrazolone product (monitored by TLC), the aromatic aldehyde derivative 3a-i (5 mmol) and the 4-hydroxycoumarin derivative 4 (5 mmol) were added simultaneously to the reaction mixture after dissolving them in 5 mL of ethanol separately and finally supplemented with 10 mL of water. The resulting mixture was stirred under reflux conditions and the progress of the reac- tion was monitored by TLC. After completion of the reaction, the mixture was filtered directly under heat. Then the products were washed with a hot ethanol-H 2 O (1:1) mixture and dried at room temperature to give the corresponding benzylpyrazolyl-coumarin derivatives 5a-i . All products were identified by melting point mea- surement and the structure of compound 5a was confirmed by mass and NMR spectroscopic methods.

References: [1]Patent: CN108948019,2018,A .Location in patent: Paragraph 0639; 0641; 0642.
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2739 - 2752.
[3]Russian Journal of Organic Chemistry,2020,vol. 56,p. 485 - 490.
Zh. Org. Khim.,.
[4]Patent: WO2008/121861,2008,A2 .Location in patent: Page/Page column 67-68.
[5]RSC Advances,2014,vol. 4,p. 61193 - 61199.
[6]Research on Chemical Intermediates,2016,vol. 42,p. 3169 - 3181.
[7]Journal of the Iranian Chemical Society,2013,vol. 10,p. 213 - 219.
[8]Patent: WO2014/138979,2014,A1 .Location in patent: Page/Page column 21; 22; 23.
[9]Patent: CN106831585,2017,A .Location in patent: Paragraph 0018; 0019; 0020.
[10]Patent: CN107235903,2017,A .Location in patent: Paragraph 0019; 0020.
[11]Patent: CN106883177,2017,A .Location in patent: Paragraph 0019; 0020.
[12]Patent: CN107235904,2017,A .Location in patent: Paragraph 0019; 0020.
[13]Patent: CN108117538,2018,A .Location in patent: Paragraph 0018; 0019; 0020.
[14]Research on Chemical Intermediates,2019,vol. 45,p. 4383 - 4394.
[15]Synthetic Communications,2021,vol. 51,p. 2336 - 2348.
[16]Journal of Molecular Structure,2022,vol. 1261.

6
[ 120-21-8 ]
[ 145091-87-8 ]
[ 1068515-75-2 ]
[ 900098-54-6 ]

Yield	Reaction Conditions	Operation in experiment
34%; 28%	In methanol; for 16h;Heating / reflux;	EXAMPLE 14Synthesis of 4,4'-((4-(diethylamino)phenyl)methylene)jb/s(5-methyl-1 /-/-pyrazol-3(2H)- one) and 4-(4-(diethylamino)benzylidene)-3-methyl-1 A7-pyrazol-5(4H)-one; To a solution of <strong>[145091-87-8]3-methyl-1H-pyrazol-5-ol</strong> (0.50 g, 5.10 mmol) in anhydrous methanol (30 mL) was added 4-(diethylamino)benzaldehyde (0.90 g, 5.10 mmol) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was cooled to ambient temperature, during which time a bright orange precipitate was deposited. The solid was collected by suction filtration, washed with methanol (10 mL), air-dried and dried under high vacuum to afford 4,4'-((4-(diethylamino)phenyl)methylene)b/s(5- methyl-1H-pyrazol-3(2H)-one) in 28% yield (0.26 g): mp 223-224 0C (methanol); 1H NMR (300 MHz,) δ 11.45 (br s, 4H), 6.90 (d, J = 8.8 Hz, 2H), 6.51 (d, J = 8.8 Hz, 2H), 4.66 (s, 1 H), 3.25 (q, J = 7.0 Hz, 4H), 2.07 (s, 6H), 1.02 (t, J = 7.0 Hz, 6H); 13C NMR (75 MHz, DMSO-Gf6) 5 161.4, 145.4, 139.7, 129.9, 128.2, 111.3, 104.9, 43.7, 31.8, 12.5, 10.4; MS (ES-) m/z 354.1 (M - 1 ). The mother liquors were concentrated in vacuo and the residue was purified by column chromatography eluted with 1% 7 M methanolic ammonia in ethyl acetate, to afford 4-(4-(diethylamino)benzylidene)-3- <n="92"/>methyl-1H-pyrazol-5(4H)-one as an orange solid in 34% yield (0.45 g): mp 207-208 0C (ethyl acetate/methanol); 1H NMR (300 MHz, CDCI3) δ 8.57 (br s, 1 H), 8.53 (d, J = 9.1 Hz, 2H), 7.19 (s, 1 H), 6.70 (d, J = 9.1 Hz1 2H), 3.47 (q, J = 7.0 Hz, 4H), 2.21 (s, 3H), 1.23 (t, J = 7.0 Hz, 6H); 13C NMR (75 MHz, CDCI3) δ 166.6, 151.8, 151.7, 147.1 , 137.5, 121.7, 119.1 , 111.2, 45.0, 13.7, 12.8; MS (ES+) m/z 258.3 (M + 1 )

References: [1]Patent: WO2008/121861,2008,A2 .Location in patent: Page/Page column 90-91.

7
[ 485-47-2 ]
[ 145091-87-8 ]
[ 1437802-73-7 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 94%	With acetic acid; at 20℃; for 0.166667h;	The substrate <strong>[145091-87-8]5-methyl-2H-pyrazole-3-ol</strong> (1.00 g, 10.2 mmol) was added to a solution of ninhydrin (1.82 g, 10.2 mmol) in acetic acid (10 mL). The reaction mixture was stirred at room temperature for 10 min. Yellowish white solid product 4 was filtered out and washed thoroughly with cold water. The product was crystallized from acetone-hexane mixture (1.36g, yield ~ 94%). Yellowish white solid, mp 252-254 ºC; IR (KBr): (cm-1) 3371, 1710; 1HNMR (300 MHz, d6-DMSO) δ: 10.79 (bs, 2H), 7.88-7.85 (m, 4H), 6.32(s, 1H), 2.3 (s, 3H); 13C NMR (75 MHz, d6-DMSO) δ: 198.9,157.8, 140.5, 140.1, 136.3, 123.4, 117.8, 97.6, 75.6, 11.6.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 3137 - 3143.

8
[ 6954-91-2 ]
[ 145091-87-8 ]
[ 109-77-3 ]
[ 1449513-91-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With amino-functionalized nanoporous SBA-15 (SBA-Pr-NH2) catalyst; In ethanol; at 80℃; for 0.0833333h;Microwave irradiation;Catalytic behavior;	SBA-Pr-NH2 (0.02 g) was activated into a round-bottomed flask containing a magnetic stirrer at 100 C for removal of the adsorbed water. The mixture of ninhydrin (1 mmol, 0.178 g), 1,2-aryl-diamines (1 mmol), and SBA-Pr-NH2 in 5 ml ethanol was heated and stirred at 60 C to form indenoquinoxaline A; then, after about 5 min, malono derivatives (1 mmol) and α-methylencarbonyl compounds (1 mmol)were added to the mixture of reaction for the synthesis of spiro[indeno[2,1-b]quinoxaline derivatives under reflux condition using MW irradiation (400 W, 80 C). Completion of the reaction was monitored by TLC. After that, obtainedprecipitate was cooled to room temperature and extractedfrom the solvent. Subsequently, the precipitate was dissolvedin minimum volume of hot acetone and the unsolvable SBA-Pr-NH2 catalyst was removed by filtration. The residue was purified by recrystallization from ethanol. The new compound was characterized by mass, IR, and NMR spectroscopy techniques. The melting points of the products were compared with those reported in the literature.
93%	With sodium carbonate; In ethanol; at 70℃; for 12h;	General procedure: To a neat solution containing 11H-indeno[1,2-b]quinoxalin-11-one (1 mmol), pyrazolone (1 mmol), and malononitrile (1 mmol), 10% mol of Na2CO3 in ethanol(10 mL) was added. The reaction mixture was heated at 70 8C for 12 h. After completion of the reaction as indicated by TLC, the precipitate was filtrated and washed with cold ethanol to afford the pure product 8. 4.5 6'-Amino-3'-methyl-1'H-spiro [indeno[1,2-b] quinoxaline-11, 4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile (8a) Light green powder (0.36 g, yield 93%). Mp 263-266 C. IR (KBr) (vmax/cm-1): 3450, 3274, 3250, 3112, 2976, 2191, 1637, 1607, 1465, 1401. 1H NMR (250 MHz, DMSO-d6): δH (ppm) 1.12 (3H, s, CH3), 7.45-8.13 (10H, m, H-Ar and NH2), 12.51 (1H, s, NH). C NMR (62 MHz, DMSO-d6): δC (ppm), 9.5 (CH3), 56.5 (C-Spiro), 96.8 (C-CN), 119.3 (CN), 121.4, 122.1, 126.2, 129.4, 129.6, 130.1, 130.8, 133.5, 135.5, 136.0, 141.8,142.5, 151.4, 153.3, 155.9, 162.9 (C-Ar and C-Pyrazole), 164.8 (C-NH2). Anal. calcd for C22H14N6O: C, 69.83; H, 3.73; N, 22.21. Found: C, 69.88; H, 3.72; N, 22.22.

References: [1]Journal of the Iranian Chemical Society,2018,vol. 15,p. 1153 - 1161.
[2]Comptes Rendus Chimie,2013,vol. 16,p. 773 - 777.

9
[ 145091-87-8 ]
7-methyl-11H-indeno[1,2-b]quinoxalin-11-one [ No CAS ]
[ 109-77-3 ]
[ 1449513-92-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate; In ethanol; at 70℃; for 12h;	General procedure: To a neat solution containing 11H-indeno[1,2-b]quinoxalin-11-one (1 mmol), pyrazolone (1 mmol), and malononitrile (1 mmol), 10% mol of Na2CO3 in ethanol(10 mL) was added. The reaction mixture was heated at 70 8C for 12 h. After completion of the reaction as indicated by TLC, the precipitate was filtrated and washed with cold ethanol to afford the pure product 8. 4.6 6'-amino-3', 7-dimethyl-1'H-spiro [indeno[1,2-b]quinoxaline-11',4-pyrano[2,3-c] pyrazole] carbonitrile (8b) Light brown powder (0.35 g, yield 90%). Mp 258-262 C. IR (KBr) 3445, 3250, 3224, 2966, 3110, 2193, 1638, 1597, 1447, 1398. 1H NMR (250 MHz, DMSO-d6): δH (ppm) 1.13 (3H, s, CH3), 2.58 (3H, s, CH3-Ar), 7.32-8.14 (9H, m, H-Ar and NH2), 12.6 (1H, s, NH). 13C NMR (62 MHz, DMSO-d6): δC (ppm) 8.9 (CH3), 21.1 (CH3-Ar), 56.5 (C-Spiro), 96.3 (C-CN), 118.7 (CN), 121.4, 125.6, 127.8, 128.6, 129.4, 131.5, 132.7, 135.6, 139.7, 140.4, 142.0, 150.8, 152.6, 155.0, 162.4 (C-Ar and C-Pyrazole), 163.3 (C-NH2). Anal. calcd for C23H16N6O: C, 70.40; H, 4.11; N, 21.42. Found: C, 70.44; H, 4.14; N, 21.39.
89%	With amino-functionalized nanoporous SBA-15 (SBA-Pr-NH2) catalyst; In ethanol; at 80℃; for 0.0833333h;Microwave irradiation;	SBA-Pr-NH2 (0.02 g) was activated into a round-bottomed flask containing a magnetic stirrer at 100 C for removal of the adsorbed water. The mixture of ninhydrin (1 mmol, 0.178 g), 1,2-aryl-diamines (1 mmol), and SBA-Pr-NH2 in 5 ml ethanol was heated and stirred at 60 C to form indenoquinoxaline A; then, after about 5 min, malono derivatives (1 mmol) and α-methylencarbonyl compounds (1 mmol)were added to the mixture of reaction for the synthesis of spiro[indeno[2,1-b]quinoxaline derivatives under reflux condition using MW irradiation (400 W, 80 C). Completion of the reaction was monitored by TLC. After that, obtainedprecipitate was cooled to room temperature and extractedfrom the solvent. Subsequently, the precipitate was dissolvedin minimum volume of hot acetone and the unsolvable SBA-Pr-NH2 catalyst was removed by filtration. The residue was purified by recrystallization from ethanol. The new compound was characterized by mass, IR, and NMR spectroscopy techniques. The melting points of the products were compared with those reported in the literature.

References: [1]Comptes Rendus Chimie,2013,vol. 16,p. 773 - 777.
[2]Journal of the Iranian Chemical Society,2018,vol. 15,p. 1153 - 1161.

10
[ 141-97-9 ]
[ 302-01-2 ]
[ 145091-87-8 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 20℃; for 0.0833333h;	General procedure: A solution containing 1,3-ketoester (1.0 equiv) andhydrazines (1.1 equiv) in ethanol (10 mL) was stirred atroom temperature for 5 min. After the reaction wascompleted, the solution was diluted with ethanol(10 mL) and stirred in an ice bath for 30 min. Theresultant solid was filtrated, washed with cold ethanol(10 mL), and recrystallized from ethanol to give purepyrazolones.

References: [1]Comptes Rendus Chimie,2013,vol. 16,p. 773 - 777.

11
[ 145091-87-8 ]
[ 51395-52-9 ]

References: [1]RSC Advances,2014,vol. 4,p. 10180 - 10187.

12
[ 574-98-1 ]
[ 145091-87-8 ]
[ 1608125-62-7 ]

Yield	Reaction Conditions	Operation in experiment
24%	In 1,4-dioxane; at 180℃; for 1h;Microwave irradiation;	Compound 42 (500 mg, 5.10 mmol) and N-(2-bromoethyl)-phthalimide (1.29 g, 5.58 mmol) were suspended in 1,4-dioxane (3 mL) in a microwave reaction vial containing a Teflon stir bar. The vial was capped and the reaction mixture was irradiated with microwaves at 180 C for 1 h at normal absorption with cooling activated. The reaction solvent was evaporated under vacuum, and the crude was purified by flash chromatography on silica gel using gradient 0-10% methanol in dichloromethane to afford product 43 (335 mg, 24%); 1H NMR (CDCl3) δ 1.98 (s, 3H), 3.10 (s, 2H), 3.94 (s, 4H), 7.68-7.70 (m, 2H), 7.80-7.82 (m, 2H).
	In 1,4-dioxane; at 180℃;Microwave irradiation;	Compound 42 (500 mg) and /V-(2-bromo ethyl)-phthalimide (1.3 g) were suspended in 1 ,4-dioxane (3mL) in a Biotage Initiator microwave reaction vial containing a Teflon stir bar. The vial was capped and the reaction mixture was transferred to the microwave and irradiated at 180 C at normal absorption with cooling activated. The reaction solvent was evaporated and the resulting crude was purified by flash chromatography on silica gel using gradient 0-10% MeOH-DCM to afford product 43.

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2739 - 2752.
[2]Patent: WO2014/138979,2014,A1 .Location in patent: Page/Page column 21.

13
[ 1020724-91-7 ]
[ 145091-87-8 ]
[ 1608125-67-2 ]
[ 1608125-68-3 ]

Yield	Reaction Conditions	Operation in experiment
7%; 3%	With caesium carbonate; In acetonitrile; at 80℃; for 2h;	Compound 42 (104 mg, 1.06 mmol) and cesium carbonate (346 mg, 1.06 mmol) were suspended in anhydrous acetonitrile (2 mL). Compound 12 (266 mg, 1.06 mmol) was dissolved in 2 mL of anhydrous acetonitrile and added dropwise to above suspension. The reaction was then continued 80 C for 2 h. The solvent was removed evaporated and the resulting crude was purified by column chromatography on silica gel using gradient 0-3% methanol in dichloromethane to give products 49 (19 mg, 7%) and 50 (8 mg, 3%) as white solids. Compound 49: mp 186-188 C, 1H NMR (CDCl3) δ 2.23 (s, 3H), 2.34 (s, 3H), 5.11 (s, 2H), 5.52 (s, 1H), 6.37 (s, 1H), 7.30-7.36 (m, 1H), 7.42 (t, J = 7.91 Hz, 2H), 7.55 (d, J = 7.53 Hz, 2H); MS ESI (+ve) for C15H16N4O (M+H+): calcd 269.14; found: 263.23. Compound 50: 1H NMR (CDCl3) δ 1.92 (s, 3H), 2.28 (s, 3H), 5.00 (s, 2H), 5.40 (s, 1H), 5.97 (s, 1H), 7.32-7.58 (m, 5H); MS ESI (+ve) for C15H16N4O (M+H+): calcd 269.14, found: 269.23.

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2739 - 2752.

14
[ 1608125-48-9 ]
[ 145091-87-8 ]
[ 1608125-67-2 ]
[ 1608125-68-3 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In acetonitrile; at 80℃; for 2h;	Compound 42 (104 mg) and cesium carbonate (346 mg) were suspended in anhydrous AcCN (2ml_). Compound 13 (200 mg) was dissolved in 2ml_ of anhydrous AcCN and added drop wise to above reaction suspension. The reaction was stirred for 2h at 80 C. The reaction solvent was removed and was purified by column chromatography to give products 49 and 50, as white solids. Compound 49, H NMR (CDCy (s, 1 H), 6.37 (s, 1 H), 7.30 - 7.36 (m, 1 H), 7.42 (t, J = 7.91 Hz, 2H), 7.55 (d, J = 7.53 Hz, 2H). Compound 50, H NMR (CDCI3) (s, 1 H), 7.32 - 7.58 (m, 5H). Compound 49, MS ESI (+ve) for C15H16N40 was calculated 312.182, and found 312.283 for (M+H+). Compound 50, MS ESI (+ve) for C15H16N40 was calculated 327.140, and found 327.261 for (M+H+).

References: [1]Patent: WO2014/138979,2014,A1 .Location in patent: Page/Page column 23.

15
[ 145091-87-8 ]
5-amino-4-<(4-nitrophenyl)azo>-3-methyl-1-phenyl pyrazole [ No CAS ]
4-(4'-(p-nitrophenylazo)-3'-methyl-1'-phenylpyrazole-5'-ylazo)-5-hydroxy-3-methyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		General procedure: 5-Amino-4-arylazo-3-methyl-1-phenylpyrazoles (0.01 mol) weredissolved in a mixture of glacial acetic acid and concentrated hydrochloricacid (20 ml, ratio 1:1) and the solutionwas then cooled to 0-5 C. Sodiumnitrite (0.69 g, 0.01 mol) in water (10 ml) was then added to this solution dropwise with vigorous stirring, for about 1 h, while cooling at0-5 C. Then the resulting diazonium solution was added in portionsover 30 min to a vigorously stirred solution of <strong>[145091-87-8]5-hydroxy-3-methyl-1H-pyrazole</strong> or 5-hydroxy-3-methyl-1-phenylpyrazole (0.01 mol) in KOH (0.56 g, 0.01mol) andwater (10ml) between 0 and 5 C,maintainingthe pHat 7-8 by simultaneous sodiumacetate solution addition. The mixture was then stirred for 2 h at 0-5 C. The precipitated product separated upon dilution with water (50 ml) was filtered off, washed with water several times, dried and crystallized from DMF-H2O