[ CAS No. 950-81-2 ]

Name: 950-81-2|1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde|95%
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SKU: A707889
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Quality Control of [ 950-81-2 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 950-81-2 ]

CAS No. :	950-81-2	MDL No. :	MFCD00003144
Formula :	C₁₂H₁₂N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QFYZFYDOEJZMDX-UHFFFAOYSA-N
M.W :	216.24 g/mol	Pubchem ID :	70371
Synonyms :

Safety of [ 950-81-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 950-81-2 ]

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

Upstream synthesis route of [ 950-81-2 ]
Downstream synthetic route of [ 950-81-2 ]

[ 950-81-2 ] Synthesis Path-Upstream 1~1

1
[ 950-81-2 ]
[ 83-10-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: With sodium chlorite; potassium phosphate monohydrate In water; <i>tert</i>-butyl alcohol at 0 - 20℃; Stage #2: With sodium chlorate In water; <i>tert</i>-butyl alcohol	Preparation Example 11,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid; 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, which is one of the intermediate compounds used in the synthesis of the compound of the present invention, was prepared as follows: To a mixture of 1-benzyl-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxaldehyde (1 g, 4.624 mmol) in butyl alcohol were added to NaClO₂(1.254 g, 13.873 mmol) in an aqueous solution and potassium phosphate monobasic monohydrate (3.146 g, 23.12 mmol) in an aqueous solution slowly at 0° C. The resulting reaction mixture was slowly heated to room temperature and stirred for 10 hours. NaClO₃(1 g) was further added while monitoring the reaction. Following the addition of sodium chlorite, the reaction mixture was stirred and then extracted with ethyl acetate. The organic layer was washed with, dried with Na₂SO₄and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was washed with 20percent ethyl acetate solution in small amount of hexane. The target compound was obtained as a white solid (808 mg, 3.48 mmol, 75percent yield).¹H NMR (400 MHz, DMSO): 12.22 (br s, 1H), 7.61-7.42 (m, 5H), 3.36 (s, 3H), 2.59 (s, 3H).

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 1858 - 1867
[2] Patent: US2011/183983, 2011, A1, . Location in patent: Page/Page column 20-21
[3] Pharmazie, 1956, vol. 11, p. 191,193
[4] Justus Liebigs Annalen der Chemie, 1949, vol. 563, p. 1,9
[5] Chemical and Pharmaceutical Bulletin, 1958, vol. 6, p. 374,376
[6] Patent: US2010/22529, 2010, A1, . Location in patent: Page/Page column 18

[ 950-81-2 ] Synthesis Path-Downstream 1~58

1
[ 950-81-2 ]
[ 83-10-3 ]

Yield	Reaction Conditions	Operation in experiment
75%		Preparation Example 11,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid; 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, which is one of the intermediate compounds used in the synthesis of the compound of the present invention, was prepared as follows: To a mixture of 1-benzyl-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxaldehyde (1 g, 4.624 mmol) in butyl alcohol were added to NaClO2 (1.254 g, 13.873 mmol) in an aqueous solution and potassium phosphate monobasic monohydrate (3.146 g, 23.12 mmol) in an aqueous solution slowly at 0 C. The resulting reaction mixture was slowly heated to room temperature and stirred for 10 hours. NaClO3 (1 g) was further added while monitoring the reaction. Following the addition of sodium chlorite, the reaction mixture was stirred and then extracted with ethyl acetate. The organic layer was washed with, dried with Na2SO4 and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was washed with 20% ethyl acetate solution in small amount of hexane. The target compound was obtained as a white solid (808 mg, 3.48 mmol, 75% yield).1H NMR (400 MHz, DMSO): 12.22 (br s, 1H), 7.61-7.42 (m, 5H), 3.36 (s, 3H), 2.59 (s, 3H).
		Preparation 143 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid To a mixture of 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde (2 g, 9.25 mmol) in water (100 mL) at 75 C. is added a solution of KMnO4 (1.5 g, 9.49 mmol) in water (200 mL) slowly. After the addition is complete, the reaction mixture is stirred at 75 C. for another 1 hour. Solid KOH is added to make the solution alkaline and the mixture is filtered while it is hot. To the filtrate is added EtOH (10 mL) and EtOAc (50 mL). The organic phase is separated and discarded. The aqueous phase is acidified with concentrated HCl to pH 5 and extracted with EtOAc (60 mL) and DCM (60 mL). The organic phases are combined, dried, and concentrated to give the title product (1.9 g, 88.46%yield). MS (m/z): 233.1 (M+H).

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1858 - 1867
[2]Patent: US2011/183983,2011,A1 .Location in patent: Page/Page column 20-21
[3]Pharmazie,1956,vol. 11,p. 191,193
[4]Justus Liebigs Annalen der Chemie,1949,vol. 563,p. 1,9
[5]Chemical and pharmaceutical bulletin,1958,vol. 6,p. 374,376
[6]Patent: US2010/22529,2010,A1 .Location in patent: Page/Page column 18

2
[ 120-72-9 ]
[ 950-81-2 ]
<4-Antipyryl-><3-indolyl->carbenium-tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrafluoroboric acid In diethyl ether; dichloromethane for 0.5h;

Reference： [1]Akguen, Eyuep; Tunali, Mustafa [Archiv der Pharmazie, 1988, vol. 321, p. 9 - 11]

3
[ 120-72-9 ]
[ 950-81-2 ]
3,3'-Diindolyl-4-(4-antipyryl)methane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In methanol for 1h;

Reference： [1]Akguen, Eyuep; Tunali, Mustafa [Archiv der Pharmazie, 1988, vol. 321, p. 921 - 924]

4
[ 95-20-5 ]
[ 950-81-2 ]
<4-Antipyryl-><2-methyl-3-indolyl->carbenium-tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrafluoroboric acid In diethyl ether; dichloromethane for 0.5h;

Reference： [1]Akguen, Eyuep; Tunali, Mustafa [Archiv der Pharmazie, 1988, vol. 321, p. 9 - 11]

5
[ 95-20-5 ]
[ 950-81-2 ]
3,3'-Di(2-methyl-indolyl)-4-(4-antipyryl)methane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In methanol for 1h;

Reference： [1]Akguen, Eyuep; Tunali, Mustafa [Archiv der Pharmazie, 1988, vol. 321, p. 921 - 924]

6
[ 603-76-9 ]
[ 950-81-2 ]
<4-Antipyryl-><1-methyl-3-indolyl->carbenium-tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With tetrafluoroboric acid In diethyl ether; dichloromethane for 0.5h;

Reference： [1]Akguen, Eyuep; Tunali, Mustafa [Archiv der Pharmazie, 1988, vol. 321, p. 9 - 11]

7
[ 603-76-9 ]
[ 950-81-2 ]
3,3'-Di(1-methyl-indolyl)-4-(4-antipyryl)methane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In methanol for 1h;

Reference： [1]Akguen, Eyuep; Tunali, Mustafa [Archiv der Pharmazie, 1988, vol. 321, p. 921 - 924]

8
[ 875-79-6 ]
[ 950-81-2 ]
<4-Antipyryl-><1,2-dimethyl-3-indolyl->carbenium-tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrafluoroboric acid In diethyl ether; dichloromethane for 0.5h;

Reference： [1]Akguen, Eyuep; Tunali, Mustafa [Archiv der Pharmazie, 1988, vol. 321, p. 9 - 11]

9
[ 875-79-6 ]
[ 950-81-2 ]
3,3'-Di(1,2-dimethyl-indolyl)-4-(4-antipyryl)methane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	In methanol for 1h;

Reference： [1]Akguen, Eyuep; Tunali, Mustafa [Archiv der Pharmazie, 1988, vol. 321, p. 921 - 924]

10
[ 10432-44-7 ]
[ 950-81-2 ]
[ 112906-25-9 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1987,vol. 52,p. 1561 - 1565

11
[ 60-80-0 ]
[ 33513-42-7 ]
[ 950-81-2 ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.5h; Stage #2: antipyrine Heating;
69%	With trichlorophosphate Reflux;
68%	With trichlorophosphate at 0 - 85℃; for 3.5h;

With trichlorophosphate chloroform, toluene, 1.) 10 deg C, 2.) 3.5 h, 60-65 deg C; Yield given. Multistep reaction;

Reference： [1]Fadda, Ahmed A.; El-Mekawy, Rasha E.; El-Shafei, Ahmed I. [Journal of Porphyrins and Phthalocyanines, 2015, vol. 19, # 6, p. 753 - 768]
[2]Fadda, Ahmed A.; El-Mekawy, Rasha E.; El-Shafei, Ahmed I. [Journal of Porphyrins and Phthalocyanines, 2015, vol. 19, # 6, p. 753 - 768]
[3]Zhang, Kaifan; Yang, Chi; Yao, Hequan; Lin, Aijun [Organic Letters, 2016, vol. 18, # 18, p. 4618 - 4621]
[4]Kokkinos, Konst.; Markopoulos, Chr. [Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 4, p. 543 - 553]

12
[ 950-81-2 ]
[ 109-77-3 ]
[ 84921-03-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	In ethanol; acetic acid for 15h; Heating;
85%	In ethanol for 0.5h; Heating;
	With piperidine In ethanol at 0℃;

Reference： [1]Zahran, Magdy A.-H.; El-Essawy, Farag A.-A.; Yassin, Salah M.; Salem, Tarek A.-R.; Boshta, Nader M. [Archiv der Pharmazie, 2007, vol. 340, # 11, p. 591 - 598]
[2]El Sakka; Kandil; El Moghayar [Archiv der Pharmazie, 1983, vol. 316, # 1, p. 76 - 82]
[3]Silva, Daniel; Mendes, Eduarda; Summers, Eleanor J.; Neca, Ana; Jacinto, Ana C.; Reis, Telma; Agostinho, Paula; Bolea, Irene; Jimeno, M. Luisa; Mateus, M. Luisa; Oliveira-Campos, Ana M. F.; Unzeta, Mercedes; Marco-Contelles, José; Majekova, Magdalena; Ramsay, Rona R.; Carreiras, M. Carmo [Drug Development Research, 2020, vol. 81, # 2, p. 215 - 231]

13
[ 950-81-2 ]
[ 13623-94-4 ]
1,2-Dihydro-1-methyl-5-nitro-2-phenyl-6-methylthio-3H-indazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.75h; Stage #2: 1,1-di(methylsulfanyl)-2-nitroethylene In tetrahydrofuran at -78℃;

Reference： [1]Roy, Amrita; Reddy, Kethiri R.; Ila, Hiriyakkanavar; Junjappa, Hiriyakkanavar [Journal of the Chemical Society. Perkin transactions I, 1999, # 20, p. 3001 - 3004]

14
[ 950-81-2 ]
[ 762-42-5 ]
1,2-Dihydro-5,6-bis(methoxycarbonyl)-1-methyl-2-phenyl-3H-indazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.75h; Stage #2: dimethyl acetylenedicarboxylate In tetrahydrofuran at 20℃;

Reference： [1]Roy, Amrita; Reddy, Kethiri R.; Ila, Hiriyakkanavar; Junjappa, Hiriyakkanavar [Journal of the Chemical Society. Perkin transactions I, 1999, # 20, p. 3001 - 3004]

15
[ 14741-71-0 ]
[ 950-81-2 ]
[ 105-56-6 ]
2-cyano-3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-1-oxo-1,5-dihydro-benzo[4,5]imidazo[1,2-a]pyridine-4-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 202 - 209

16
[ 14741-71-0 ]
[ 950-81-2 ]
[ 109-77-3 ]
1-amino-2-cyano-3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-1,2-dihydro-benzo[4,5]imidazo[1,2-a]pyridine-4-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 202 - 209

17
[ 14741-71-0 ]
[ 950-81-2 ]
[ 284497-12-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 202 - 209

18
[ 950-81-2 ]
[ 613-94-5 ]
[ 76644-54-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride In ethanol for 4h; Heating;
	With hydrogenchloride In ethanol; water for 6h; Reflux;
	Stage #1: benzoic acid hydrazide With hydrogenchloride In ethanol; water Reflux; Stage #2: 4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one In ethanol; water for 6h; Reflux;

Reference： [1]Radhakrishnan; Raju [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2005, vol. 44, # 9, p. 1812 - 1816]
[2]Location in patent: experimental part Ajithkumar; Radhakrishnan [Journal of the Indian Chemical Society, 2010, vol. 87, # 3, p. 253 - 260]
[3]Ajithkumar; Radhakrishnan [Journal of the Indian Chemical Society, 2012, vol. 89, # 10, p. 1329 - 1333]

19
[ 461015-77-0 ]
[ 950-81-2 ]
9-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylmethyl)-3-isobutyl-1-propyl-1,4,9-triaza-spiro[5.5]undecane-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 20℃; for 36h;

Reference： [1]Habashita, Hiromu; Kokubo, Masaya; Hamano, Shin-ichi; Hamanaka, Nobuyuki; Toda, Masaaki; Shibayama, Shiro; Tada, Hideaki; Sagawa, Kenji; Fukushima, Daikichi; Maeda, Kenji; Mitsuya, Hiroaki [Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4145 - 4152]

20
[ 30414-53-0 ]
[ 950-81-2 ]
[ 80880-62-2 ]
[ 533939-12-7 ]

Yield	Reaction Conditions	Operation in experiment
36%	With hydrogenchloride In methanol; n-heptane; 2,2,2-trifluoroethanol; ethyl acetate	5.1 Part 1 Part 1 2,6-Diethyl-pyridine-3,5-dicarboxylic acid dimethyl Ester A mixture of methyl-3-oxo-pentanoate (3.15 g, 24.2 mmol), methyl-3-amino-pentenoate (3.15 g, 24.3 mmol) and 4-antipyrinecarboxaldehyde (5.00 g, 23.1 mmol) in 2,2,2-trifluroethanol (4 mL) in a teflon screwcap glass pressure vessel is heated to 100° C. with stirring overnight. After cooling to room temperature, the contents of the vessel are transferred to a flask containing methanol (10 mL) and concentrated hydrochloric acid (4.0 mL, 48 mmoL), and the mixture is stirred at 90° C. for 6 h. The contents are poured into 50% aq NaHCO3 (100 mL), extracted with ethyl acetate (2*50 mL) and dried over Na2SO4. The crude material is purified by medium-pressure liquid chromatography (MPLC) on silica (5-50% ethyl acetate in heptane) to afford the product as a white solid (2.1 g, 36%); Rf 0.55 (30% ethyl acetate in heptane); 1H NMR (CDCl3, 300 MHz) δ8.64 (s, 1 H), 3.93 (s, 6 H), 3.20 (q, J=7.5 Hz, 4 H), 1.31 (t, J=7.5 Hz, 6 H); ESI-LCMS m/z calcd for C13H17NO4: 251.1; found 252.0 (M+1)+.

Reference： [1]Current Patent Assignee: INSTITUES FOR PHARMACEUTICAL D; INSTITUTE FOR DIABETES DISCOVERY; INSTITUTES FOR PHARMACEUTICAL DISCOVERY - US2003/166668, 2003, A1

21
[ 950-81-2 ]
[ 95-54-5 ]
[ 21627-62-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With silica gel; dimethyl sulfoxide In dichloromethane for 0.416667h; microwave irradiation;
	In ethanol for 3h; Reflux;

22
[ 950-81-2 ]
[ 13331-31-2 ]
[ 1156535-67-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	In isopropyl alcohol at 20℃; for 2h;

Reference： [1]Location in patent: experimental part Abdelhamid, Abdou O.; Afifi, Mamdouh A. M. [Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 11, p. 2703 - 2713]

23
[ 950-81-2 ]
[ 51529-97-6 ]
[ 105-56-6 ]
[ 1217319-12-4 ]

Reference： [1]Acta poloniae pharmaceutica,2009,vol. 66,p. 259 - 270

24
[ 950-81-2 ]
[ 51529-97-6 ]
[ 109-77-3 ]
[ 1217319-24-8 ]

Reference： [1]Acta poloniae pharmaceutica,2009,vol. 66,p. 259 - 270

25
[ 950-81-2 ]
[ 56553-60-7 ]
[ 617714-23-5 ]
[ 750633-86-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one; 5-(3,4-Dichloro-benzyl)-2-aza-bicyclo[2.2.2]octane In 1,2-dichloro-ethane at 20℃; for 0.25h; Stage #2: sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃;	2 EXAMPLE 2 4-[5-(3,4-Dichloro-benzyl)-2-aza-bicyclo[2.2.2]oct-2-ylmethyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one To a solution of 5-(3,4-dichloro-benzyl)-2-aza-bicyclo[2.2.2]octane (0.05 g, 0.35 mmol) in 2 ml of DCE was added 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde (90 mg, 1.2 eq.), and the mixture was stirred at rt for 15 min. NaBH(OAc)3 (0.11 g, 1.5 eq.) was then added and the mixture was stirred at rt overnight, then with NaHCO3 (sat.), and extracted with EtOAc. The EtOAc layer was washed with NaCl (sat.), dried over Na2SO4 and concentrated.Preparative TLC with 10% (10% NH4OH in MeOH) in CH2Cl2 gave 82 mg of Example 2 (M++1: 470).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2004/176416, 2004, A1 Location in patent: Page/Page column 11

26
[ 950-81-2 ]
[ 5702-70-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide at 100℃;

Reference： [1]Location in patent: experimental part Augustine, John Kallikat; Atta, Rajendra Nath; Ramappa, Balakrishna Kolathur; Boodappa, Chandrakantha [Synlett, 2009, # 20, p. 3378 - 3382]

27
[ 950-81-2 ]
[ 13680-35-8 ]
[ 1296869-06-1 ]

Yield	Reaction Conditions	Operation in experiment
41.4%	With formic acid; In methanol; for 4h;Reflux; Inert atmosphere;	General procedure: A methanolic solution of antipyrine-4-carboxaldehyde (0.432 g, 2 mmol) was added to a methanolic solution of 4,4'-methylene bis-(2,6-dimethyl aniline) (0.254 g, 1 mmol) in a 50 mL Schlenk flask under a nitrogen atmosphere. A catalytic amount of formic acid was added and the reaction mixture was kept at refluxing temperature for 4 h, and then cooled to room temperature. A pale yellow solid was separated by filtration and purified by column chromatography using hexane/ethyl acetate as eluant (8:2 v/v). The product (L1) was dried under vacuum at room temperature and stored in a vacuum desiccator. The reactions involved in the preparation of the ligands are outlined in Fig. 1. Yield: 46.3%.

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 1887 - 1894

28
[ 950-81-2 ]
[ 19900-69-7 ]
[ 1296869-05-0 ]

Yield	Reaction Conditions	Operation in experiment
38.1%	With formic acid In methanol for 4h; Reflux; Inert atmosphere;	2.5.1. Preparation of the ligands (L¹-L³) General procedure: A methanolic solution of antipyrine-4-carboxaldehyde (0.432 g, 2 mmol) was added to a methanolic solution of 4,4'-methylene bis-(2,6-dimethyl aniline) (0.254 g, 1 mmol) in a 50 mL Schlenk flask under a nitrogen atmosphere. A catalytic amount of formic acid was added and the reaction mixture was kept at refluxing temperature for 4 h, and then cooled to room temperature. A pale yellow solid was separated by filtration and purified by column chromatography using hexane/ethyl acetate as eluant (8:2 v/v). The product (L1) was dried under vacuum at room temperature and stored in a vacuum desiccator. The reactions involved in the preparation of the ligands are outlined in Fig. 1. Yield: 46.3%.

Reference： [1]Location in patent: experimental part Budagumpi, Srinivasa; Liu, Yinshan; Suh, Hongsuk; Kim, Il [Journal of Organometallic Chemistry, 2011, vol. 696, # 9, p. 1887 - 1894]

29
[ 950-81-2 ]
[ 4073-98-7 ]
[ 1296869-07-2 ]

Yield	Reaction Conditions	Operation in experiment
46.3%	With formic acid; In methanol; for 4h;Reflux; Inert atmosphere;	General procedure: A methanolic solution of antipyrine-4-carboxaldehyde (0.432 g, 2 mmol) was added to a methanolic solution of 4,4'-methylene bis-(2,6-dimethyl aniline) (0.254 g, 1 mmol) in a 50 mL Schlenk flask under a nitrogen atmosphere. A catalytic amount of formic acid was added and the reaction mixture was kept at refluxing temperature for 4 h, and then cooled to room temperature. A pale yellow solid was separated by filtration and purified by column chromatography using hexane/ethyl acetate as eluant (8:2 v/v). The product (L1) was dried under vacuum at room temperature and stored in a vacuum desiccator. The reactions involved in the preparation of the ligands are outlined in Fig. 1. Yield: 46.3percent.

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 1887 - 1894

30
[ 12107-56-1 ]
[ 950-81-2 ]
[ 4073-98-7 ]
[ 1296869-08-3 ]

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 1887 - 1894

31
[ 12107-56-1 ]
[ 950-81-2 ]
[ 13680-35-8 ]
[ 1296869-09-4 ]

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 1887 - 1894

32
[ 950-81-2 ]
[ 1357598-13-0 ]
[ 1357597-91-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium acetate; acetic acid for 6h; Heating;	5.3. Reaction of thiazolidin-5-one derivative 4 with aromatic aldehydes General procedure: To a solution of compound 4 (0.41 g, 0.001 mol) and anhydrous sodium acetate (0.12 g, 0.0015 mol) in glacial acetic acid (10 mL), was added an appropriate aromatic aldehydes (0.001 mol). The reaction mixture was heated for 6 h, where upon the solid product partially crystallized out. The reaction mixture was left to cool and the separated solid product was filtered off, washed with water, dried, and recrystallized from ethanol to give compounds 5a,b.

Reference： [1]Location in patent: experimental part Bondock, Samir; Adel, Shymaa; Etman, Hassan A.; Badria, Farid A. [European Journal of Medicinal Chemistry, 2012, vol. 48, p. 192 - 199]

33
[ 2295-31-0 ]
[ 29921-57-1 ]
[ 950-81-2 ]
[ 1374999-94-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: thiazoline-2,4-dione With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Stage #2: isopropyl 2-bromoacetate In tetrahydrofuran; mineral oil for 3h; Reflux; Cooling with ice; Stage #3: 4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one With sodium acetate at 140℃; for 0.5h; neat (no solvent);

Reference： [1]Location in patent: experimental part Nishida, Sho; Maruoka, Hiroshi; Yoshimura, Yuki; Goto, Takao; Tomita, Ryoko; Masumoto, Eiichi; Okabe, Fumi; Yamagata, Kenji; Fujioka, Toshihiro [Journal of Heterocyclic Chemistry, 2012, vol. 49, # 2, p. 303 - 309]

34
[ 950-81-2 ]
[ 17403-09-7 ]
4-((4-(1H-indol-3-yl)piperidin-1-yl)methyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 4h; Inert atmosphere;	9 4.1.2.6.1. General procedure A General procedure: Aldehyde (1.5 eq.) and amine (1 eq.) were mixed in 1,2-dichloroethane, followed by addition of sodium triacetoxyborohydride (1.4 eq.). The reaction was stirred at room temperature under inert atmosphere for 4 h. The reaction mixture was quenched with sat. aq. NaHCO3, and the product was extracted with ethyl acetate. The organic phasewas dried (Na2SO4),and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography with ethyl acetate/acetonitrile:water:methanol (1:1:1) to afford the desired product.

Reference： [1]Santos, Sofia A.; Lukens, Amanda K.; Coelho, Lis; Nogueira, Fátima; Wirth, Dyann F.; Mazitschek, Ralph; Moreira, Rui; Paulo, Alexandra [European Journal of Medicinal Chemistry, 2015, vol. 102, p. 320 - 333]

35
[ 109-97-7 ]
[ 950-81-2 ]
5,10,15,20-mesotetrakis[1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-y]-21H,23H-porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 150℃; for 1h; Dean-Stark; Inert atmosphere;
82%	With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 150℃; for 1h; Inert atmosphere; Dean-Stark;

36
[ 950-81-2 ]
[ 79-19-6 ]
[ 96715-43-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	In neat (no solvent) at 20℃; for 1h; Milling; Green chemistry;	3.2.1. Solid-State Synthesis of Thiosemicarbazones 1-3 General procedure: A mixture of thiosemicarbazide (0.182 g, 2.00 mmol) and 2.00 mmol of 4-formylantipyrine,2-acetylpyrrole or camphor was ball-milled at room temperature for 1 h. The resulting solid powderswere dried at 80 C under vacuum to give a 100% yield of the corresponding thiosemicarbazones 1, 2and 3 that did not require any further purification. 4-Formylantipyrine thiosemicarbazone (1). White solid; yield 100%; m.p. 219-220 °C (Lit. yield 88%;m.p. 217-219 °C [10]); IR: ν= 3378, 3236 (NH and NH2), 1682 (C=O) cm1; 1H-NMR (CDCl3): δ = 2.45 (s, 3H, CH3), 3.20 (s, 3H, CH3N), 7.00-7.45 (m, 5H, Ar-H), 8.00 (s, 2H, NH2), 8.40 (s, 1H,CH=N), 9.55 (s, 1H, NH). Anal. Calcd. for C13H15N5OS (289.36): C, 53.96; H, 5.23; N, 24.20%. Found:C, 53.83; H, 5.28; N, 24.32%.
	With acetic acid In ethanol for 3h; Reflux;

Reference： [1]Gaffer, Hatem E.; Khalifa, Mohamed E. [Molecules, 2015, vol. 20, # 12, p. 21982 - 21991]
[2]Bari, Ahmed; Grenier, Daniel; Azelmat, Jabrane; Syed, Saeed Ali; Al-Obaid, Abdulrahman M.; Hosten, Eric C. [Chemical Biology and Drug Design, 2019, vol. 94, # 4, p. 1750 - 1759]

37
[ 950-81-2 ]
[ 1303507-75-6 ]
3-(benzyloxy)-2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-5,5-dimethyloxazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate at 20℃; for 2h; Sealed tube;

Reference： [1]Zhang, Kaifan; Yang, Chi; Yao, Hequan; Lin, Aijun [Organic Letters, 2016, vol. 18, # 18, p. 4618 - 4621]

38
[ 950-81-2 ]
[ 95-55-6 ]
4-(2-hydroxyphenylimino)methyl-1,5-dimethyl-2-phenylpyrazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In ethanol at 40℃; for 2h;	Preparation of the ligand The ligand(HACAP) was prepared bycondensing antipyrine-4-carboxaldehyde with anethanolic solution of 2-aminophenol in 1:1 molarratio. The mixture was stirred for about 2 h at 400C.Pale yellow coloured crystals separated werefiltered, washed successively with ethanol andether, recrystallized from ethanol (90% yield, m.p.120oC).

Reference： [1]Thomas, Preethy Soosan; Philip, Surya; Mohanan [Oriental Journal of Chemistry, 2017, vol. 33, # 6, p. 2787 - 2795]

39
[ 950-81-2 ]
[ 89-25-8 ]
(Z)-1,4-dimethyl-5-((3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)methyl)-2-phenyl-1,2-dihydro-3H-pyrazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With piperidine; acetic acid Reflux;	Procedure for the preparation of 3-methyl-5-pyrazolone derivatives 2a,b General procedure: For the preparation of 4-arylidene-3-methyl-1-phenyl-5-pyrazolone derivatives (2 a,b) we used the reported method of utilizing the 3-methyl-1-phenyl-5-pyrazolone (1) with aromatic aldehydes either antipyrine aldehyde or pipronal aldehyde to afford 2a and 2b respectively. The reaction was carried out by reacting 1 with aromatic aldehydes to form 4-arylidene-3-methyl-1-phenyl-5-pyrazolone derivatives 2 a,b in the presence of mixture of piperidine and glacial acetic acid. The final products were obtained in good yields after recrystallization from ethanol. (Z)-1,4-dimethyl-5-((3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)methyl)-2-phenyl-1,2-dihydro-3H-pyrazol-3-one (2a): Bright orange needles, 85 % yield, mp. 179oC,C22H20N4O2, 372.43 g/mol, IR(cm-1): 1589 (C=C), 1621 (C=O), 2924, 3069 (CH), EI-MS: m/z: 373.11[M++H]+,1H-NMR (500 MHZ, DMSO-d6) δ (ppm):2.11 (s, 6H, 2CH3); 3.38(s, 3H, NCH3); 7.34 (s, 1H, CH=C), 7.51(dd, 4H, ArH), 7.65(d, 2H, ArH), 7.84(d, 4H, ArH), 13C NMR (100 MHz, DMSO-d6) δ (ppm): 25.26X2 (2CH3), 51.18 (NCH3), 109.15, 110.90, 114.31, 118.56, 125.19, 127.00, 130.00, 137.16, 145.80, 167.01 (C=O)., EA: Calcd. C, 70.95, H, 5.41, N, 15.04, Found C, 70.93, H, 5.40, N, 15.05, Rf : 0.32 (25% EtAc / cyclohexan).

Reference： [1]El Sayed, Mardia T.; El-Sharief, Marwa A.M.Sh.; Zarie, Eman S.; Morsy, Nesrin M.; Elsheakh, Ahmed R.; Voronkov, Andrey; Berishvili, Vladimir; Hassan, Ghada S. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 5, p. 952 - 957]

40
[ 950-81-2 ]
[ 591-27-5 ]
4-[(3-hydroxyphenyl)-imino]methyl}-1,5-dimethyl-2-phenyl-1,2-dihydro-3Hpyrazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In ethanol for 4h; Reflux;	3-Aminophenol (0.22 g, 2 mmol) was dissolved in 20 mL ethanol and added to 4-antipyrine carboxaldehyde (0.43 g, 2 mmol) in 30 mL ethanol. The 1:1 mixture was refluxed on a boiling water bath for 4 h, the excess of solvent was partially evaporated and yellow solid was separated by adding drops of cold water. It was filtered and washed with water followed by ether. The ligand was then recrystallized from ethanol and dried under vacuum over anhydrous CaCl2. The purity of the ligand was checked by TLC, infrared and NMR spectra and by elemental analysis. Yield: 71 %, m.p.: 208 °C. 1H NMR (DMSO-d6) (δ, ppm): 8.83 (s, 1H, phenolic),8.31 (s, 1H, -CH=N-), 5.9-7.54 (m,-Ph) 3.34 (s, 3H, -N-CH3),2.9 (s, 3H, =C-CH3). IR (KBr, cm-1): ~3370 ν(OH), 1641 ν(C=O),1588 ν(C=N), 1275 ν(ph-O). Anal. calcd. for C18H17N3O2(307.35): C, 70.34; H, 5.6; N, 13.67. Found C, 69.8; H, 5.3;N, 13.7 %.

Reference： [1]Jincy; Nair, M.K. Muraleedharan [Asian Journal of Chemistry, 2018, vol. 30, # 5, p. 1037 - 1043]

41
[ 950-81-2 ]
1,5-dimethyl-2-phenyl-3-thioxo-2,3-dihydro-1H-pyrazole-4-carbothialdehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetraphosphorus decasulfide In tetrahydrofuran at 20℃; for 10h;

Reference： [1]Abd-El-Maksoud, Mansoura A.; Khatab, Tamer K.; Maigali, Soher S.; Soliman, Fouad M.; Hamed, Ahmed A. [Journal of Heterocyclic Chemistry, 2018, vol. 55, # 12, p. 2883 - 2892]

42
[ 950-81-2 ]
1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbothialdehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With 2,4-bis(phenylthio)-1,3-dithia-2λ⁵,4λ⁵-diphosphetane 2,4-disulphide In tetrahydrofuran at 20℃; for 12h;

Reference： [1]Abd-El-Maksoud, Mansoura A.; Khatab, Tamer K.; Maigali, Soher S.; Soliman, Fouad M.; Hamed, Ahmed A. [Journal of Heterocyclic Chemistry, 2018, vol. 55, # 12, p. 2883 - 2892]

43
[ 7677-24-9 ]
[ 950-81-2 ]
2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-hydroxyacetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃;	16.1; 31.1 Step 1: Preparation of 2-(1,5-dimethyl-3-oxo-2-phenyl-2,3- dihydro-1H-pyrazol-4-yl)-2-hydroxyacetonitrile. A solution of trimethysilyf cyanide (1.1 equiv) in acetonitrile (0.1 M) is added to a solution of l,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-l/:/-pyrazole-4-carbaldehyde (1 equiv) and 1,5,7- Triazabicyclo[4.4.0]dec-5-ene (1 equiv) in acetonitrile (0.1 M), and the reaction mixture is stirred for three hours. The crude mixture is diluted with IN aqueous hydrochloric acid solution and ethyl acetate followed by addition of saturated aqueous sodium bicarbonate solution, and the layers are separated. The organic layer is washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material is purified by silica gel column chromatography (0-50% ethyl acetate/hexanes) to afford 2-(1,5-dimethyl-3-oxo-2-phenyl-2,3- dihydro-1H-pyrazol-4-yl)-2-hydroxyacetonitrile.

Reference： [1]Current Patent Assignee: C4 THERAPEUTICS INC - WO2019/99868, 2019, A2 Location in patent: Page/Page column 360; 372; 373

44
[ 7677-24-9 ]
[ 950-81-2 ]
[ 616-34-2 ]
methyl (cyano(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methyl)glycinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one; methoxycarbonylmethylamine With triethylamine In methanol at 20℃; for 0.0833333h; Stage #2: trimethylsilyl cyanide With boron trifluoride diethyl etherate In methanol at 20℃;	28.1 Step 1: Preparation of Methyl (Cyano(l,5-dimethyI-3-oxo-2-phenyl-2, 3-dihydro- l/Z- pyrazol-4-yl)methyl)glycinate To a stirred solution of l,5-dimethyl-3-oxo-2-phenyl-2, 3-dihydro- li7-pyrazole-4- carbaldehyde (1 equiv) and methyl glycinate (1.5 equiv) in methanol (0.2 M) at room temperature is added tri ethyl amine (1.5 equiv), and the mixture is stirred for five minutes. Borontrifluoride diethyletherate (1.5 equiv) and trimethyl silyl cyanide (1.5 equiv) is then added. Upon consumption of the aldehyde starting material, the reaction mixture is partitioned between ethyl acetate and water. The layers are separated, and the aqueous phase is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel column chromatography provides methyl (cyano(l,5~dimethyl-3-oxo~2~phenyl-2,3~dihydro-l i-pyrazol-4-yi)methyl)glycinate.

Reference： [1]Current Patent Assignee: C4 THERAPEUTICS INC - WO2019/99868, 2019, A2 Location in patent: Page/Page column 369

45
[ 950-81-2 ]
[ 78364-55-3 ]
C₁₉H₁₆FN₅OS [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2019,vol. 94,p. 1750 - 1759

46
[ 950-81-2 ]
2-(4-(benzo[d]thiazol-2-yl)-2-methoxyphenoxy)propane hydrazide [ No CAS ]
(E,Z)-2-(4-(benzo[d]thiazol-2-yl)-2-methoxyphenoxy)-N′-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methylene)propane hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With acetic acid In ethanol for 1h; Reflux;	4.1.1.4 General procedure for the synthesis of (E,Z)-2-(4-(benzo[d]thiazol-2-yl)-2-methoxyphenoxy)-N′-substituted propane hydrazides (6a-j, 7a-i, 8a,b) General procedure: The propane hydrazide compound 5 (1.0g, 3.0mmol) was refluxed with the appropriate aldehyde or ketone derivative (3.0mmol) in absolute ethanol (10ml) in presence of few drops of glacial acetic acid for 1h (aldehydes or acyclic ketones) and 3h (cyclic ketones) and the reaction was monitored by TLC. The reaction mixture was subsequently cooled to r.t. and filtered to give the crude product which was further purified by crystallization from methanol.

Reference： [1]Ghannam, Iman A.Y.; Abd El-Meguid, Eman A.; Ali, Islam H.; Sheir, Donia H.; El Kerdawy, Ahmed M. [Bioorganic Chemistry, 2019, vol. 93]

47
[ 950-81-2 ]
[ 1456732-30-1 ]
5-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methyleneamino)-3-(p-methoxyphenylamino)-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With acetic acid In ethanol for 1h; Reflux;	General method for synthesis of double pyrazole Schiff bases (6a-d and 7a-d) or pyrazole Schiff bases (8a-d and 9a-d): General procedure: Compounds 1a-d (0.01 mol) were mixed with 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1Hpyrazole-4-carbaldehyde (2), 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3), 4-(piperidin-1-yl)benzaldehyde (4), or 3,4,5-trimethoxybenzaldehyde (5) in absolute EtOH (25 mL) and a catalytic amount of glacial acetic acid (1 mL). The reaction mixture was refluxed for one hour; the solid product obtained on hot was filtered o and recrystallized from EtOH to afford the corresponding new bis-pyrazole Schiff bases 6a-d, 7a-d or mono-pyrazole Schiff bases 8a-d and 9a-d, respectively. 5-((1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methyleneamino)-3-(p-methoxyphenylamino)-1H-pyrazole-4-carboxamide (6a): Yellow crystals; melting point: 274-276 °C; yield: 79%. IR (KBr)νmax/cm-1 3359, 3165 (NH, NH2), 1675, 1654 (2C=O). 1H-NMR (400 MHz) δppm: 2.61 (s, 3H, CH3),3.37 (s, 3H, NCH3), 3.70 (s, 3H, OCH3), 6.85 (d, 2H, J = 8.2 Hz, ArH), 7.19 (s, 1H, NH2-amide,exchangeable with D2O), 7.37 (d, 2H, J = 7.4 Hz, ArH), 7.45-7.48 (m, 3H, ArH), 7.56 (t, 2H, ArH),7.80 (s, 1H, NH2-amide, exchangeable with D2O), 8.68 (s, 1H, -CH=N-), 8.85, 12.37 (2s, 2H, 2NH,exchangeable with D2O). 13C-NMR (101 MHz) δ ppm: 11.50 (CH3), 33.93 (NCH3), 55.21 (OCH3),101.94, 105.97, 114.24, 117.08, 126.85, 128.42, 129.38, 133.70, 135.49, 144.36, 148.19, 153.38, 154.30, 156.79(18C), 162.54 (C=O, amide), 166.76 (C=O, antipyrine). MS (m/z, %): 445 (M+, 13.44). Anal. Calcd. (%)for C23H23N7O3 (445.47): C, 62.01; H, 5.20; N, 22.01. Found: C, 62.23; H, 5.07; N, 22.16.

Reference： [1]Hassan, Ashraf S.; Askar, Ahmed A.; Naglah, Ahmed M.; Naglah, Ahmed M.; Almehizia, Abdulrahman A.; Ragab, Ahmed [Molecules, 2020, vol. 25, # 11]

48
[ 950-81-2 ]
5-amino-3-[(4-methoxyphenyl)amino]-N-phenyl-1H-pyrazole-4-carboxamide [ No CAS ]
5-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methyleneamino)-3-(p-methoxyphenylamino)-N-phenyl-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic acid In ethanol for 1h; Reflux;	General method for synthesis of double pyrazole Schiff bases (6a-d and 7a-d) or pyrazole Schiff bases (8a-d and 9a-d): General procedure: Compounds 1a-d (0.01 mol) were mixed with 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1Hpyrazole-4-carbaldehyde (2), 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3), 4-(piperidin-1-yl)benzaldehyde (4), or 3,4,5-trimethoxybenzaldehyde (5) in absolute EtOH (25 mL) and a catalytic amount of glacial acetic acid (1 mL). The reaction mixture was refluxed for one hour; the solid product obtained on hot was filtered o and recrystallized from EtOH to afford the corresponding new bis-pyrazole Schiff bases 6a-d, 7a-d or mono-pyrazole Schiff bases 8a-d and 9a-d, respectively.

Reference： [1]Hassan, Ashraf S.; Askar, Ahmed A.; Naglah, Ahmed M.; Naglah, Ahmed M.; Almehizia, Abdulrahman A.; Ragab, Ahmed [Molecules, 2020, vol. 25, # 11]

49
[ 950-81-2 ]
5-amino-N-(4-chlorophenyl)-3-[(4-methoxyphenyl)amino]-1H-pyrazole-4-carboxamide [ No CAS ]
N-(4-chlorophenyl)-5-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methyleneamino)-3-(p-methoxyphenylamino)-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic acid In ethanol for 1h; Reflux;	General method for synthesis of double pyrazole Schiff bases (6a-d and 7a-d) or pyrazole Schiff bases (8a-d and 9a-d): General procedure: Compounds 1a-d (0.01 mol) were mixed with 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1Hpyrazole-4-carbaldehyde (2), 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3), 4-(piperidin-1-yl)benzaldehyde (4), or 3,4,5-trimethoxybenzaldehyde (5) in absolute EtOH (25 mL) and a catalytic amount of glacial acetic acid (1 mL). The reaction mixture was refluxed for one hour; the solid product obtained on hot was filtered o and recrystallized from EtOH to afford the corresponding new bis-pyrazole Schiff bases 6a-d, 7a-d or mono-pyrazole Schiff bases 8a-d and 9a-d, respectively.

Reference： [1]Hassan, Ashraf S.; Askar, Ahmed A.; Naglah, Ahmed M.; Naglah, Ahmed M.; Almehizia, Abdulrahman A.; Ragab, Ahmed [Molecules, 2020, vol. 25, # 11]

50
[ 950-81-2 ]
5-amino-3-[(4-methoxyphenyl)amino]-N-(4-methylphenyl)-1H-pyrazole-4-carboxamide [ No CAS ]
5-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methyleneamino)-3-(p-methoxyphenylamino)-N-p-tolyl-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With acetic acid In ethanol for 1h; Reflux;	General method for synthesis of double pyrazole Schiff bases (6a-d and 7a-d) or pyrazole Schiff bases (8a-d and 9a-d): General procedure: Compounds 1a-d (0.01 mol) were mixed with 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1Hpyrazole-4-carbaldehyde (2), 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3), 4-(piperidin-1-yl)benzaldehyde (4), or 3,4,5-trimethoxybenzaldehyde (5) in absolute EtOH (25 mL) and a catalytic amount of glacial acetic acid (1 mL). The reaction mixture was refluxed for one hour; the solid product obtained on hot was filtered o and recrystallized from EtOH to afford the corresponding new bis-pyrazole Schiff bases 6a-d, 7a-d or mono-pyrazole Schiff bases 8a-d and 9a-d, respectively.

Reference： [1]Hassan, Ashraf S.; Askar, Ahmed A.; Naglah, Ahmed M.; Naglah, Ahmed M.; Almehizia, Abdulrahman A.; Ragab, Ahmed [Molecules, 2020, vol. 25, # 11]

51
[ 950-81-2 ]
[ 1187-42-4 ]
C₁₆H₁₄N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With sulfuric acid In ethanol at 20℃;	2.2. Synthesis of probe ANTI-DMN To a solution of 4-antipyrene carboxaldehyde (0.25 g, 11.6 mmol)and diaminomaleonitrile (0.125 g, 11.6 mmol) in ethanol (6 mL), fewdrops of Conc. H2SO4 was added and stirred at room temperature. Theprogress of the reaction was monitored by TLC, after the completion ofthe reaction the greenish yellow colored solid was filtered, dried andthen recrystallized from methanol. The obtained target compound wasconfirmed by various spectral techniques (ANTI-DMN): yield 87%. 1HNMR (400 MHz, DMSO-d6) δ: 8.10 (s, 1H), 7.58-7.54 (t, J = 7.6 Hz,2H), 7.48-7.44 (t, J = 7.4 Hz, J = 4.2 Hz, 1H), 7.37-7.35 (d,J = 7.2 Hz, 2H), 7.22 (s, 2H), 3.34 (s, 3H), 2.66 (s, 3H).13C NMR(100 MHz, DMSO-d6) δ: 164.31, 153.12, 150.06, 134.28, 129.84,128.71, 127.02, 123.70, 115.51, 114.53, 106.13, 101.82, 34.22, 13.09.FT-IR (cm-1): 3445 and 3317 (NeH stretching), 3166 (AreCeH), 3035(aliphatic CeH), 2241 and 2196 (-CN), 1662 (-HC = N). 1H-1H COSYNMR spectrum. HRMS: the calculated mass of ANTI-DMN: 306.1229obtained mass: 306.1227 (Fig. S1-S5).

Reference： [1]Karuppusamy, P.; Sarveswari, S. [Inorganica Chimica Acta, 2021, vol. 515]

52
[ 948864-23-1 ]
[ 950-81-2 ]
5-((2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)methyleneamino)-3-(phenylamino)-N-(4-methylphenyl)-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With acetic acid In ethanol for 1h; Reflux;	General method for synthesis of Schiff bases linked with heterocyclic moiety (6a-c, 7a-c, 11a-c, 12a-c, and 13a-c) General procedure: A mixture of 5-aminopyrazoles 4a-c (0.01 mol) and the appropriate heteroaromatic aldehydes (0.01 mol) fnamely; 4-antipyrinecarboxaldehyde (5a), 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (5b), 4-(piperidin-1-yl) benzaldehyde (8), thiophene-2-carbaldehyde (9), and nicotinaldehyde (10) g with a catalytic amount of glacial acetic acid (1 ml) in absolute ethanol (25 ml) was refluxed for one hour and then left tocool. The solid product was filtered off, dried and finally recrystallized from ethanol to afford the corresponding Schiff bases (6a-c, 7a-c, 11a-c, 12a-c, and 13a-c).

Reference： [1]Mukhtar, Shorouk S.; Hassan, Ashraf S.; Morsy, Nesrin M.; Hafez, Taghrid S.; Saleh, Fatma M.; Hassaneen, Hamdi M. [Synthetic Communications, 2021, vol. 51, # 10, p. 1564 - 1580]

53
[ 950-81-2 ]
[ 785778-44-1 ]
N-(4-chlorophenyl)-5-(((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methylene)amino)-3-(phenylamino)-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With acetic acid In ethanol for 1h; Reflux;	General method for synthesis of Schiff bases linked with heterocyclic moiety (6a-c, 7a-c, 11a-c, 12a-c, and 13a-c) General procedure: A mixture of 5-aminopyrazoles 4a-c (0.01 mol) and the appropriate heteroaromatic aldehydes (0.01 mol) fnamely; 4-antipyrinecarboxaldehyde (5a), 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (5b), 4-(piperidin-1-yl) benzaldehyde (8), thiophene-2-carbaldehyde (9), and nicotinaldehyde (10) g with a catalytic amount of glacial acetic acid (1 ml) in absolute ethanol (25 ml) was refluxed for one hour and then left tocool. The solid product was filtered off, dried and finally recrystallized from ethanol to afford the corresponding Schiff bases (6a-c, 7a-c, 11a-c, 12a-c, and 13a-c).

Reference： [1]Mukhtar, Shorouk S.; Hassan, Ashraf S.; Morsy, Nesrin M.; Hafez, Taghrid S.; Saleh, Fatma M.; Hassaneen, Hamdi M. [Synthetic Communications, 2021, vol. 51, # 10, p. 1564 - 1580]

54
[ 950-81-2 ]
[ 107463-56-9 ]
5-((2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)methyleneamino)-N-phenyl-3-(phenylamino)-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic acid In ethanol for 1h; Reflux;	General method for synthesis of Schiff bases linked with heterocyclic moiety (6a-c, 7a-c, 11a-c, 12a-c, and 13a-c) General procedure: A mixture of 5-aminopyrazoles 4a-c (0.01 mol) and the appropriate heteroaromatic aldehydes (0.01 mol) fnamely; 4-antipyrinecarboxaldehyde (5a), 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (5b), 4-(piperidin-1-yl) benzaldehyde (8), thiophene-2-carbaldehyde (9), and nicotinaldehyde (10) g with a catalytic amount of glacial acetic acid (1 ml) in absolute ethanol (25 ml) was refluxed for one hour and then left tocool. The solid product was filtered off, dried and finally recrystallized from ethanol to afford the corresponding Schiff bases (6a-c, 7a-c, 11a-c, 12a-c, and 13a-c).

Reference： [1]Mukhtar, Shorouk S.; Hassan, Ashraf S.; Morsy, Nesrin M.; Hafez, Taghrid S.; Saleh, Fatma M.; Hassaneen, Hamdi M. [Synthetic Communications, 2021, vol. 51, # 10, p. 1564 - 1580]

55
[ 950-81-2 ]
[ 140-88-5 ]
C₁₇H₁₉N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one With toluene-4-sulfonic acid hydrazide Stage #2: ethyl acrylate With tert.-butylnitrite; N,N,N,N,-tetramethylethylenediamine; copper dichloride In tetrahydrofuran at 65℃; for 24h;

Reference： [1]Bao, Xiaoguang; Cheng, Xionglve; Jiang, Gangzhong; Jin, Feng; Li, Xingxing; Ma, Liang; Tao, Suyan; Wan, Xiaobing; Yang, Jinwei [Chemical Science, 2021, vol. 12, # 28, p. 9823 - 9830]

56
[ 950-81-2 ]
[ 100-16-3 ]
C₁₈H₁₇N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sulfuric acid In methanol	2.2. Synthesis a characterization of probe L and L-Cu2+ complex To a hot solution of antipyrine carboxaldehyde (1.72 g, 10.0 mmol)in methanol (15 mL) was added slowly a solution of 4-nitro phenylhydrazine (0.16 g, 5.0 mmol) in methanol (5 mL) with continuousstirring. After the addition of a catalytic amount sulphuric acid, the reactionmixture was refluxed for 3 h. The progress of the reaction wasmonitored by TLC. The reaction mixture was cooled and the brick redprecipitate was filtered then washed with methanol several times andrecrystallized from desired solvent with a yield of 89%. recrystallized from desired solvent with a yield of 89%.Characterization of L (C18H17N5O3) (Fig. 1S-Fig. 4S): FT-IR (cm-1,Fig. 1S): 3233 (NH), 3073 (Ar-CH), 1643 (C=O), 1578 (C=N), 1472(N=O). 1H NMR of L (Fig. 2S) (400 MHz, DMSO-d6) δ (ppm): 11.05 (s,1H), 8.13(d, J = 9.2 Hz, 2H), 7.90 (s, 1H), 7.54 (t, J = 7.6 Hz, 2H), 7.41(t, J = 7.4 Hz, 1H), 7.37 (d, J = 7.6 Hz, 2H), 7.02 (d, J = 8.4 Hz, 2H),3.26 (s, 3H), 2.64 (s, 3H). 13C NMR of L (Fig. 3S) (100 MHz, DMSO-d6), δ(ppm): 169.0, 152.3, 151.0, 137.9, 136.9, 134.7, 129.7, 127.9, 126.8,125.7, 111.0, 101.4, 79.5, 34.8, 12.8. HRMS data of L (Fig. 4S) [M + H]+calculated mass: 352.1409 obtained mass: 352.1405.

Reference： [1]Shaji, Leyana K.; Ashok Kumar [Inorganic Chemistry Communications, 2021, vol. 134]

57
[ 950-81-2 ]
(Z)-2-[4-(benzo[d]thiazol-2-yl)-2-methoxyphenoxy]-N'-(4-oxothiazolidin-2-ylidene)acetohydrazide [ No CAS ]
2-[4-(benzo[d]thiazol-2-yl)-2-methoxyphenoxy]-N'-{(2Z,5Z)-[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methylene]-4-oxothiazolidin-2-ylidene}acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium acetate; acetic acid for 6h; Reflux;	4.1.3 General method for the synthesis of 2-[4-(benzo[d]thiazol-2-yl)-2-methoxyphenoxy]-N'-[(Z)-(substituted) 4-oxothiazolidin-2-ylidene]acetohydrazide (3-12) General procedure: A suspension of 4-oxothiazolidin-2-ylidene derivative 2 (1mmol, 0.43g) and different substituted aldehyde; namely, 4-cyanobenzaldehyde, 4-dimethylaminobenzaldehyde, 2,4,6-trimethylbenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 3,4-dimethoxybenzaldehyde, 3,4,5-trimethoxybenzaldehyde, 2-chloro-5-nitrobenzaldehyde, 4-chloro-3-nitrobenzaldehyde, 1H-indole-3-carbaldehyde, 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbaldehyde, respectively; (1mmol) in glacial acetic acid (10mL) containing 0.4g anhydrous sodium acetate was heated under reflux for 6h. After cooling, the reaction mixture was then poured into ice-water and the solid precipitate was filtered, dried and recrystallized from methanol to furnish the corresponding derivatives 3-12.

Reference： [1]Abd El-Meguid, Eman A.; Mohi El-Deen, Eman M.; Moustafa, Gaber O.; Awad, Hanem M.; Nossier, Eman S. [Bioorganic Chemistry, 2022, vol. 119]

58
[ 54-85-3 ]
[ 950-81-2 ]
C₁₈H₁₇N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol for 0.1h; Microwave irradiation;	Synthesis of ligand (ISAP) The ligand was prepared by microwave irradiation. About0.01 mol of antipyrine-4-carboxaldehyde was mixed with0.01 mol of isonicotinic acid hydrazide and ground in a mortar.The reaction mixture was then dissolved in 2ml of ethanoland irradiated for 6 min. A pale yellow product wasformed, which is then recrystallized with ethanol, dried undervacuum at room temperature. The purity of the reaction wasstudied using TLC (Scheme 1).

Reference： [1]Jayasree, Elambalassery G.; Mohanan, Kochukittan; Philip, Surya [Journal of Biomolecular Structure and Dynamics, 2021]

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[ CAS No. 950-81-2 ]

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[ 950-81-2 ] Synthesis Path-Upstream 1~1

[ 950-81-2 ] Synthesis Path-Downstream 1~58

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Aryls

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Pyrazoles

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