[ CAS No. 615-15-6 ] {[proInfo.proName]}

Name: 615-15-6|2-Methyl-1H-benzo[d]imidazole|98%
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Quality Control of [ 615-15-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 615-15-6 ]

CAS No. :	615-15-6	MDL No. :	MFCD00005598
Formula :	C₈H₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LDZYRENCLPUXAX-UHFFFAOYSA-N
M.W :	132.16	Pubchem ID :	11984
Synonyms :

Calculated chemistry of [ 615-15-6 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.06
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.26
Log Po/w (XLOGP3) :	1.98
Log Po/w (WLOGP) :	1.87
Log Po/w (MLOGP) :	1.32
Log Po/w (SILICOS-IT) :	2.53
Consensus Log Po/w :	1.79

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.57
Solubility :	0.353 mg/ml ; 0.00267 mol/l
Class :	Soluble
Log S (Ali) :	-2.21
Solubility :	0.818 mg/ml ; 0.00619 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.26
Solubility :	0.0721 mg/ml ; 0.000546 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.16

Safety of [ 615-15-6 ]

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 [ 615-15-6 ]

* 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 [ 615-15-6 ]
Downstream synthetic route of [ 615-15-6 ]

[ 615-15-6 ] Synthesis Path-Upstream 1~12

1
[ 615-15-6 ]
[ 1964-77-8 ]

Reference： [1] Tetrahedron Letters, 1986, vol. 27, # 9, p. 1051 - 1054
[2] Chemistry of Heterocyclic Compounds, 1997, vol. 33, # 8, p. 949 - 953
[3] Chemistry of Heterocyclic Compounds, 1997, vol. 33, # 8, p. 949 - 953

2
[ 615-15-6 ]
[ 67-66-3 ]
[ 7726-95-6 ]
[ 1964-77-8 ]
[ 1844-42-4 ]

Reference： [1] Chim. farm. Z., 1975, vol. 9, # 9, p. 18; engl. Ausg. S. 565
[2] Pakistan J. scient. ind. Res., 1972, vol. 15, p. 11

3
[ 615-15-6 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 1964-77-8 ]
[ 1844-42-4 ]

Reference： [1] Journal of the Indian Chemical Society, 1965, vol. 42, p. 777,781

4
[ 1445-45-0 ]
[ 20691-72-9 ]
[ 615-15-6 ]
[ 2818-70-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	With indium; acetic acid In ethyl acetate for 5 h; Reflux; Inert atmosphere	General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10percent NaHCO₃ (30 mL), and then extracted with ethyl acetate (30 mL.x.3). The combined organic extracts were dried over MgSO₄, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by ¹H NMR, ¹³C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

Reference： [1] Tetrahedron, 2011, vol. 67, # 41, p. 8027 - 8033

5
[ 615-15-6 ]
[ 2818-70-4 ]

Reference： [1] Chemistry of Heterocyclic Compounds, 1997, vol. 33, # 8, p. 949 - 953

6
[ 615-15-6 ]
[ 29043-48-9 ]

Reference： [1] Chemistry of Heterocyclic Compounds, 2000, vol. 36, # 4, p. 421 - 428
[2] Combinatorial Chemistry and High Throughput Screening, 2014, vol. 17, # 1, p. 89 - 95

7
[ 74949-72-7 ]
[ 95-54-5 ]
[ 3775-60-8 ]
[ 615-15-6 ]
[ 79015-02-4 ]

Reference： [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1981, vol. 21, # 6, p. 218 - 219

8
[ 615-15-6 ]
[ 3314-30-5 ]

Reference： [1] Journal of the Indian Chemical Society, 1982, vol. 59, # 3, p. 349 - 351
[2] Wiss. Z. Univ. Halle-Wittenberg, 1959, vol. 8, p. 1037
[3] Journal of Medicinal and Pharmaceutical Chemistry, 1959, vol. 1, p. 577,594

9
[ 615-15-6 ]
[ 3012-80-4 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1959, p. 343,347[2] Rev. textile-Tiba, 1958, vol. 57, p. 164,166

10
[ 615-15-6 ]
[ 570-22-9 ]
[ 5313-35-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sulfuric acid; dihydrogen peroxide In water at 100 - 130℃;	General procedure: A solution of 10.0 mmol of compound 1a–1d in 14 mL of concentrated sulfuric acid was heated to 100–105°C, 14 mL (0.26 mol) of 30percent aqueous hydrogen peroxide was added dropwise with stirring,and the mixture was stirred for 1 h at 130°C. After cooling, the mixture was poured into water and adjusted to pH 4, and the precipitate was filtered off.

Reference： [1] Russian Journal of Organic Chemistry, 2016, vol. 52, # 10, p. 1528 - 1530[2] Zh. Org. Khim., 2016, vol. 52, # 10, p. 1533 - 1535,3

11
[ 2050-85-3 ]
[ 144-62-7 ]
[ 615-15-6 ]
[ 34801-09-7 ]

Reference： [1] Gazzetta Chimica Italiana, 1901, vol. 31 I, p. 22

12
[ 64-17-5 ]
[ 367-31-7 ]
[ 615-15-6 ]
[ 118469-15-1 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 831 - 837

[ 615-15-6 ] Synthesis Path-Downstream 1~88

1
[ 56-23-5 ]
[ 34801-09-7 ]
[ 615-15-6 ]

Reference： [1]Journal of Organic Chemistry,1941,vol. 6,p. 25,28

2
[ 615-15-6 ]
[ 77-78-1 ]
[ 2876-08-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethanolamine at 20℃; for 0.0666667h; Sonication; Green chemistry;
85%	With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In benzene at 20℃; for 0.333333h;
80%	With tetrabutylammomium bromide; potassium carbonate at 20℃; for 0.166667h;

	With sodium hydroxide
	With sodium hydroxide

Reference： [1]Babu, P. N. Kishore; Devi, B. Rama; Dubey, P. K. [Asian Journal of Chemistry, 2012, vol. 24, # 12, p. 5756 - 5758,3]
[2]xxx [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 11, p. 867 - 871]
[3]Kumar, T. Ashok; Devi, B. Rama; Dubey [Asian Journal of Chemistry, 2013, vol. 25, # 17, p. 9569 - 9572]
[4]Le Bris; Wahl [Bulletin de la Societe Chimique de France, 1959, p. 343,347][Rev. textile-Tiba, 1958, vol. 57, p. 164,166]
[5]Eldebss, Taha M. A.; Farag, Ahmad M.; Shamy, Adel Y. M. [Journal of Heterocyclic Chemistry, 2019, vol. 56, # 2, p. 371 - 390]

3
[ 615-15-6 ]
[ 74-88-4 ]
[ 2876-08-6 ]

Yield	Reaction Conditions	Operation in experiment
99.3%	With potassium hydroxide; sodium chloride In water
90%	With sodium hydroxide for 0.5h; Ambient temperature;
86%	With potassium hydroxide In acetone at 20℃; for 0.5h;

79%	Stage #1: 2-Methyl-1H-benzimidazole With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: methyl iodide In tetrahydrofuran; tert-butyl methyl ether at 0 - 20℃;
73%	With potassium carbonate In ethanol at 0 - 40℃; for 16h; Schlenk technique;
65%	Stage #1: 2-Methyl-1H-benzimidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 25℃; for 12h; Inert atmosphere;
54%	With potassium hydroxide In acetone at 20℃; for 1h;
	at 100℃; im Rohr;
	With potassium hydroxide 1.) acetone, room temp., 2.) room temp., 10 min; Yield given. Multistep reaction;
	With sodium hydride In N,N-dimethyl-formamide for 24h; Heating;

Reference： [1]Popov [Chemistry of Heterocyclic Compounds, 1996, vol. 32, # 6, p. 672 - 681]
[2]Pilarski, Boguslaw [Liebigs Annalen der Chemie, 1983, # 6, p. 1078 - 1080]
[3]Taylor, Nicholas J.; Emer, Enrico; Preshlock, Sean; Schedler, Michael; Tredwell, Matthew; Verhoog, Stefan; Mercier, Joel; Genicot, Christophe; Gouverneur, Véronique [Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276]
[4]Kumar, Gulshan; Shankar, Ravi; Singh, Davinder; Tali, Javeed Ahmad [New Journal of Chemistry, 2021, vol. 45, # 44, p. 20551 - 20555]
[5]Kljajic, Marko; Puschnig, Johannes G.; Weber, Hansjörg; Breinbauer, Rolf [Organic Letters, 2017, vol. 19, # 1, p. 126 - 129]
[6]Takemura, Noriaki; Kuninobu, Yoichiro; Kanai, Motomu [Organic and Biomolecular Chemistry, 2014, vol. 12, # 16, p. 2528 - 2532]
[7]Gazit, Aviv; Yee, Kevin; Uecker, Andrea; Boehmer, Frank-D.; Sjoeblom, Tobias; Oestman, Arne; Waltenberger, Johannes; Golomb, Gershon; Banai, Shmuel; Heinrich, Michael C.; Levitzki, Alexander [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 9, p. 2007 - 2018]
[8]Fischer,O. [Chemische Berichte, 1892, vol. 25, p. 2826]
[9]Kikugawa, Yasuo [Synthesis, 1981, # 2, p. 124 - 125]
[10]Guemue, Fatma; Alguel, Oeztekin; Eren, Goekcen; Eroglu, Hatice; Diril, Nuran; Guer, Sibel; Oezkul, Aykut [European Journal of Medicinal Chemistry, 2003, vol. 38, # 5, p. 473 - 480]

4
[ 615-15-6 ]
[ 1792-40-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sulfuric acid; potassium nitrate; at 0℃; for 2.08333h;	To a mixture of compound I-1or I-2 (7 mmol) inconcentrated sulfuric acid (5 mL) at 0 oC, a solution of KNO3 (7 mmol) in concentrated sulfuric acid (5 mL) wasadded dropwise for 20 min. After stirring continuously for105 min, the reaction mixture was poured slowly to icewater(100 mL) with stirring. The precipitated product wasfiltered, washed with cold water, dried over anhydrousNa2SO4, concentrated, and purified by PTLC to give productII-1 in 88% yield or II-2 in 80% yield.
58%	With sulfuric acid; nitric acid; at 20℃; for 2h;Inert atmosphere;	Concd sulfuric acid (10 ml) was added with stirring to 2-methyl-1H-benzimidazole (0.66 g, 0.005 mol) then a nitrating mixture made from HNO3 (0.36 ml) and concd sulfuric acid (0.4 ml) was cautiously added dropwise. After stirring for 2 h, compound 7 was isolated by pouring on ice-water then neutralizing with aqueous ammonia (0.51 g, 58%) as white solid, mp 223-225 C. 1H NMR (300 MHz, CDCl3 delta 2.57 (s, 3H, CH3), 4.71 (s, 1H, NH), 7.51 (d, J = 8.8 Hz, 1H, H7), 8.09 (d, J = 8.8 Hz, 1H, H6), 8.24 (s, 1H, H4).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3288 - 3294
[2]Combinatorial Chemistry and High Throughput Screening,2014,vol. 17,p. 89 - 95
[3]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1661 - 1670
[4]Indian Journal of Heterocyclic Chemistry,2011,vol. 21,p. 97 - 98
[5]Chemische Berichte,1903,vol. 36,p. 3972
[6]Zhurnal Obshchei Khimii,1952,vol. 22,p. 1008,1014;engl.Ausg.S.1063,1067
[7]Chemistry of Heterocyclic Compounds,2000,vol. 36,p. 421 - 428
[8]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7324 - 7332
[9]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 1691 - 1700

5
[ 615-15-6 ]
[ 3314-30-5 ]

Reference： [1]Journal of the Indian Chemical Society,1982,vol. 59,p. 349 - 351
[2],1959,vol. 8,p. 1037
[3]Journal of medicinal and pharmaceutical chemistry,1959,vol. 1,p. 577,594

7
[ 881-50-5 ]
[ 615-15-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1881,vol. 209,p. 358

8
[ 2050-85-3 ]
[ 615-15-6 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 2485 - 2496
[2]Chemisches Zentralblatt,1904,vol. 75,p. 102
[3]Gazzetta Chimica Italiana,1901,vol. 31 I,p. 22
[4]Journal of the Chemical Society,1928,p. 174
[5]Chemisches Zentralblatt,1904,vol. 75,p. 102

9
[ 2050-85-3 ]
[ 144-62-7 ]
[ 615-15-6 ]
[ 34801-09-7 ]

Reference： [1]Gazzetta Chimica Italiana,1901,vol. 31 I,p. 22

10
[ 95-54-5 ]
[ 103-79-7 ]
[ 615-15-6 ]
[ 621-72-7 ]
[ 108-88-3 ]

Reference： [1]Journal of the American Chemical Society,1948,vol. 70,p. 44,48

11
[ 21508-19-0 ]
[ 615-15-6 ]
[ 22896-13-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1969,vol. 5,p. 246 - 247
Khimiya Geterotsiklicheskikh Soedinenii,1969,vol. 5,p. 325 - 327

12
[ 615-15-6 ]
[ 3395-91-3 ]
[ 138942-42-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In N,N-dimethyl-formamide;	Compound 1 is prepared by the condensation of 2-hydroxy-1-naphthaldehyde (2) and 3-(2-methyl-1H-benzimidazol-1-yl)propanohydrazide (3). The intermediate 3 was prepared through the hydrazinolysis of methyl ester 5, which in turn was prepared by the reaction of 2-methyl-1H-benzimidazole (4) with <strong>[3395-91-3]methyl 3-bromopropionate</strong> in the presence of anhydrous potassium carbonate as a base.
96%	With potassium carbonate; In N,N-dimethyl-formamide;	Compound 1 is prepared by the condensation of 2-hydroxy-1-naphthaldehyde (2) and 3-(2-methyl-1H-benzimidazol-1-yl)propanohydrazide (3). The intermediate 3 was prepared through the hydrazinolysis of methyl ester 5, which in turn was prepared by the reaction of 2-methyl-1H-benzimidazole (4) with <strong>[3395-91-3]methyl 3-bromopropionate</strong> in the presence of anhydrous potassium carbonate as a base.

Reference： [1]Heterocycles,1991,vol. 32,p. 1923 - 1931
[2]Patent: US2013/18079,2013,A1 .Location in patent: Paragraph 0145; 0146
[3]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 880 - 885
[4]Patent: US9282738,2016,B2 .Location in patent: Page/Page column 19; 20

13
[ 615-15-6 ]
[ 632-80-4 ]
[ 75998-27-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 961 - 973

14
[ 615-15-6 ]
[ 100-44-7 ]
[ 5805-83-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethanolamine at 20℃; for 0.0833333h; Sonication; Green chemistry;
90%	With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h;
82%	at 130℃; for 0.0833333h; Microwave irradiation;

65%	With cetyltrimethylammonim bromide; potassium carbonate In acetonitrile at 20℃; for 8.08333h; Reflux;	3.3. General Procedure for Preparation of N-Benzylatedbenzimidazoles 7(a-b) General procedure: A mixture of benzimidazole 6a or 6b (0.05 mol), CTAB (0.05 mol), acetonitrile (30 mL),and K2CO3 (0.1 mol) was stirred at room temperature. Benzyl chloride (0.075 mol) wasadded drop-wise to the reaction mixture over a period of 5 min. Afterwards, after stirring,and the reaction mixture was subjected to reflux for 8 h. The progress of the reaction wasmonitored by using TLC in a mixture of chloroform and methanol in a 4:1 ratio as a mobilephase. After the completion of the reaction, the contents of the flask were cooled to roomtemperature and poured into crushed ice. The crude product thus obtained was purifiedby column chromatography.
62%	for 24h; Schlenk technique; Reflux;
26%	In methanol for 40h; Heating;

Reference： [1]Babu, P. N. Kishore; Devi, B. Rama; Dubey, P. K. [Asian Journal of Chemistry, 2012, vol. 24, # 12, p. 5756 - 5758,3]
[2]Streicher, Hansjoerg; Reiner, Martin; Schmidt, Richard R. [Journal of Carbohydrate Chemistry, 1997, vol. 16, # 3, p. 277 - 298]
[3]Kumar, T. Ashok; Devi, B. Rama; Dubey [Asian Journal of Chemistry, 2013, vol. 25, # 17, p. 9569 - 9572]
[4]Ahmad, Matloob; Ashfaq, Usman Ali; Khan, Imran Ahmad; Sultan, Sadia; Zaki, Magdi E. A. [Molecules, 2021, vol. 26, # 16]
[5]Kljajic, Marko; Puschnig, Johannes G.; Weber, Hansjörg; Breinbauer, Rolf [Organic Letters, 2017, vol. 19, # 1, p. 126 - 129]
[6]Yamamoto,H.; Maruoka,K. [Journal of the American Chemical Society, 1981, vol. 103, p. 4186]

15
[ 615-15-6 ]
[ 616-38-6 ]
[ 2876-08-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 18-crown-6 ether; potassium carbonate at 100℃; for 10h;

Reference： [1]Lissel, Manfred [Liebigs Annalen der Chemie, 1987, p. 77 - 80]

16
[ 615-15-6 ]
[ 50-00-0 ]
[ 101-79-1 ]
[ 74614-50-9 ]

Reference： [1]Pharmazie,1980,vol. 35,p. 78 - 80

17
[ 615-15-6 ]
[ 1964-77-8 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 1051 - 1054
[2]Chemistry of Heterocyclic Compounds,1997,vol. 33,p. 949 - 953
[3]Chemistry of Heterocyclic Compounds,1997,vol. 33,p. 949 - 953

18
[ 93634-54-9 ]
[ 95-54-5 ]
[ 615-15-6 ]
[ 110841-84-4 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 32 - 35

19
[ 615-15-6 ]
[ 1839-17-4 ]
[ 63572-63-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1989,vol. 25,p. 783 - 790
Khimiya Geterotsiklicheskikh Soedinenii,1989,vol. 25,p. 940 - 947

20
[ 70254-61-4 ]
[ 95-54-5 ]
[ 615-15-6 ]
[ 615-16-7 ]
[ 111008-23-2 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 1389 - 1392
[2]Tetrahedron Letters,1987,vol. 28,p. 1389 - 1392

21
[ 41501-57-9 ]
[ 95-54-5 ]
[ 615-15-6 ]
[ 5465-29-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 575 - 579
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 634 - 638

22
[ 74949-72-7 ]
[ 95-54-5 ]
[ 3775-60-8 ]
[ 615-15-6 ]
[ 79015-02-4 ]

Reference： [1]Zeitschrift fur Chemie,1981,vol. 21,p. 218 - 219

23
[ 70254-61-4 ]
[ 95-54-5 ]
[ 71-36-3 ]
[ 615-15-6 ]
[ 615-16-7 ]
[ 111008-23-2 ]
[ 111008-21-0 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 1389 - 1392

24
[ 2050-85-3 ]
[ 999-97-3 ]
[ 615-15-6 ]

Reference： [1]Synthetic Communications,1988,vol. 18,p. 167 - 180

25
[ 1435-71-8 ]
[ 615-15-6 ]
[ 22876-15-9 ]
[ 88-74-4 ]
[ 2440-22-4 ]

Reference： [1]Gazzetta Chimica Italiana,1993,vol. 123,p. 683 - 686

26
[ 1435-71-8 ]
[ 615-15-6 ]
[ 617-84-5 ]
[ 22876-15-9 ]
[ 88-74-4 ]
[ 2440-22-4 ]

Reference： [1]Gazzetta Chimica Italiana,1993,vol. 123,p. 683 - 686

27
[ 34801-09-7 ]
[ 615-15-6 ]
(2-methylbenzimidazolido)phosphoric acid [ No CAS ]
(2-methylbenzimidazolido)pyrophosphoric acid [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,1994,vol. 64,p. 1174 - 1175
Zhurnal Obshchei Khimii,1994,vol. 64,p. 1306 - 1307
[2]Phosphorus, Sulfur and Silicon and the Related Elements,1996,vol. 109,p. 465 - 468

28
[ 615-15-6 ]
[ 50-00-0 ]
[ 21881-77-6 ]
2,6-Dimethyl-1-(2-methyl-benzoimidazol-1-ylmethyl)-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 917 - 919

29
[ 615-15-6 ]
[ 50-00-0 ]
[ 21829-09-4 ]
2,6-Dimethyl-1-(2-methyl-benzoimidazol-1-ylmethyl)-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 917 - 919

30
[ 39263-43-9 ]
[ 615-15-6 ]
[ 1805-65-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 853 - 858

31
[ 615-15-6 ]
[ 7044-92-0 ]
C₂₆H₂₂N₄ [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1999,vol. 35,p. 617 - 620

32
[ 1964-77-8 ]
[ 64-19-7 ]
zinc dust [ No CAS ]
[ 615-15-6 ]

Reference： [1]Chemisches Zentralblatt,1902,vol. 73,p. 940

33
[ 709-19-3 ]
soda lime [ No CAS ]
[ 615-15-6 ]
[ 15719-64-9 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1893,vol. 273,p. 315

34
[ 615-15-6 ]
[ 67-66-3 ]
[ 7726-95-6 ]
[ 1964-77-8 ]
[ 1844-42-4 ]

Reference： [1],1975,vol. 9,p. 18; engl. Ausg. S. 565
[2]Pakistan Journal of Scientific and Industrial Research,1972,vol. 15,p. 11

35
[ 615-15-6 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 1964-77-8 ]
[ 1844-42-4 ]

Reference： [1]Journal of the Indian Chemical Society,1965,vol. 42,p. 777,781

36
[ 552-32-9 ]
[ 64-19-7 ]
iron [ No CAS ]
[ 615-15-6 ]
[ 34801-09-7 ]

Reference： [1]Journal of the Chemical Society,1931,p. 1143,1153

37
[ 64-17-5 ]
[ 552-32-9 ]
ammonium hydrosulfide [ No CAS ]
[ 615-15-6 ]
[ 34801-09-7 ]
[ 13666-95-0 ]

Reference： [1]Chemische Berichte,1910,vol. 43,p. 3024

38
[ 64-17-5 ]
[ 552-32-9 ]
platinum [ No CAS ]
[ 615-15-6 ]
[ 34801-09-7 ]
[ 13666-95-0 ]

Reference： [1]Journal of the American Chemical Society,1935,vol. 57,p. 1835,1838

39
[ 7647-01-0 ]
[ 2050-85-3 ]
[ 615-15-6 ]

Reference： [1]Journal of the Chemical Society,1930,p. 1409,1413

40
[ 2050-85-3 ]
aqueous alkaline solutions [ No CAS ]
[ 615-15-6 ]

Reference： [1]Journal of the Chemical Society,1930,p. 1409,1413

41
[ 615-15-6 ]
[ 5181-35-1 ]
2-[2-(2-methyl-benzoimidazol-1-yl)-ethoxy]-isoindole-1,3-dione [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,2000,vol. 77,p. 300 - 301

42
[ 615-15-6 ]
[ 17649-86-4 ]
[ 528877-71-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 2-Methyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Stage #2: 4,4-bis(methylthio)but-3-en-2-one In tetrahydrofuran at 0 - 20℃;

Reference： [1]Panda, Kausik; Suresh; Ila; Junjappa [Journal of Organic Chemistry, 2003, vol. 68, # 9, p. 3498 - 3506]

43
[ 615-15-6 ]
[ 1483-73-4 ]
[ 1484-39-5 ]

Reference： [1]Journal of Chemical Research,2004,p. 206 - 207

44
[ 615-15-6 ]
[ 29043-48-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2000,vol. 36,p. 421 - 428
[2]Combinatorial Chemistry and High Throughput Screening,2014,vol. 17,p. 89 - 95

45
[ 615-15-6 ]
[ 1849-01-0 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1997,vol. 33,p. 949 - 953
[2]Chemistry of Heterocyclic Compounds,1997,vol. 33,p. 949 - 953

46
[ 615-15-6 ]
[ 207557-35-5 ]
[ 521267-64-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 101 (2S)-1-[1,1-Dimethyl-3-(2-methyl-benzoimidazol-1-yl)-propylamino]-acetyl}-pyrrolidine-2-carbonitrile Synthesis of this compound required the preparation of the corresponding amine precursor IIIL. This compound is accessible in analogy to the synthesis of the pyrazol type amines IIIH by replacing the pyrazole starting materials XXII with imidazoles XXVIII. Imidazoles XXVIII used in examples 101-105 are commercially available, known in the literature or were prepared in analogy to literature procedures. Similarly, regioisomers (e.g. XXIX-A and XXIX-B) may be formed in the alkylation of XXVIII that are isolated individually, deprotected by acid treatment to give amines IIIL. Amines IIIL are subsequently used in the final coupling step with IIA to furnish cyanopyrrolidines I. The title compound was obtained in analogy to example 78, steps C] to E] by replacing 5-methyl-3-phenyl-1H-pyrazole with commercially available 2-methylbenzimidazole. The desired compound was obtained as the free amine as a glass. MS (ISP): 354.3 (MH+).

Reference： [1]Patent: US2003/130281,2003,A1

47
[ 95-54-5 ]
[ 615-15-6 ]
[ 2876-08-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium hydroxide In acetic acid	EXAMPLES Phenylene diamine (32 grams) and glacial acetic acid (60 ml) were refluxed for 2 hours. Ice and KOH were added to bring the pH to 8.0, and the resulting light violet solid was filtered and collected. Recrystallization from benzene yielded 30 grams of 2-methyl benzimidazole as a light yellow solid having a melting point of 170° C. and total yield of 77%. Synthesis of 1,2-dimethyl benzimidazole:

Reference： [1]Current Patent Assignee: HEBREW UNIVERSITY OF JERUSALEM; Yissum Research & Development (in: Hebrew University) - US2002/28817, 2002, A1

48
[ 615-15-6 ]
[ 2876-08-6 ]

Yield	Reaction Conditions	Operation in experiment
6 grams (54%)	With potassium hydroxide In acetone, methyl iodide; water	EXAMPLES To 10 grams of 2-methyl benzimidazole (75 mM), crushed 25 grams of crushed KOH (450 mM) in 300 ml acetone, methyl iodide (15 grams, 105 mM) was added at a continuous drip for 0.5 hours, at room temperature. Following additional 0.5 hour, water was added, the reaction extracted with dichloromethane, evaporated and chromatographed on silica gel to yield 6 grams (54%) of 1,2-dimethyl benzimidazole as a white solid having a melting point of 102° C.

Reference： [1]Current Patent Assignee: HEBREW UNIVERSITY OF JERUSALEM; Yissum Research & Development (in: Hebrew University) - US2002/28817, 2002, A1

49
[ 615-15-6 ]
[ 2876-08-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium hydroxide In dimethyl sulfoxide at 20℃;
	With potassium carbonate

Reference： [1]Infante-Castillo, Ricardo; Rivera-Montalvo, Luis A.; Hernández-Rivera, Samuel P. [Journal of Molecular Structure, 2008, vol. 877, # 1-3, p. 10 - 19]
[2]Gondal, Humaira Yasmeen; Ali, Muhammad [Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 5, p. 1343 - 1348]

50
[ 615-15-6 ]
[ 14024-63-6 ]
Zn(acetylacetonate)2(2-methylbenzimidazole) [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1982,vol. 59,p. 992 - 994

51
[ 95-54-5 ]
[ 1558-82-3 ]
[ 615-15-6 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 5883 - 5886

52
[ 64-17-5 ]
[ 367-31-7 ]
[ 615-15-6 ]
[ 118469-15-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2010,vol. 83,p. 831 - 837

53
[ 1445-45-0 ]
[ 20691-72-9 ]
[ 615-15-6 ]
[ 2818-70-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	With indium; acetic acid; In ethyl acetate; for 5h;Reflux; Inert atmosphere;	General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8027 - 8033

54
[ 615-15-6 ]
[ 2144-37-8 ]
C₁₅H₁₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;	General procedure: A solution of this chloromethyl ester (1.8 mmol) in N,N-dimethylformamide (4 ml) was treated with the 2-substituted benzimidazoles (1.8 mmol) and cesium carbonate (2.8 mmol). The mixture was stirred for 3 h at r.t. and partitioned with water and ethyl acetate (20 ml). The aqueous layer was further extracted with ethyl acetate (20 ml) and the combined organic layers washed with brine (20 ml), dried (sodium sulfate), filtered and concentrated. Flash chromatography with ethyl acetate provided the desired product as colored oil.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5549 - 5555

55
[ 13570-08-6 ]
[ 615-15-6 ]

Reference： [1]Research on Chemical Intermediates,2012,vol. 38,p. 1403 - 1409

56
[ 615-15-6 ]
[ 1798-83-0 ]
[ 52331-81-4 ]

Reference： [1]Central European Journal of Chemistry,2012,vol. 10,p. 1516 - 1526,11

57
[ 615-15-6 ]
[ 5409-58-5 ]
[ 1425336-21-5 ]

Reference： [1]Central European Journal of Chemistry,2012,vol. 10,p. 1516 - 1526,11

58
[ 615-15-6 ]
[ 5409-58-5 ]
[ 1425337-17-2 ]

Reference： [1]Central European Journal of Chemistry,2012,vol. 10,p. 1516 - 1526,11

59
[ 615-15-6 ]
[ 14651-42-4 ]
[ 1415725-25-5 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 13633 - 13637

60
[ 615-15-6 ]
[ 88-74-4 ]
[ 6965-02-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iron; sulfur at 150℃; for 24h; Inert atmosphere;

Reference： [1]Nguyen, Thanh Binh; Ermolenko, Ludmila; Al-Mourabit, Ali [Journal of the American Chemical Society, 2013, vol. 135, # 1, p. 118 - 121]

61
[ 34801-09-7 ]
[ 124-38-9 ]
[ 615-15-6 ]

Reference： [1]Green Chemistry,2013,vol. 15,p. 95 - 99
[2]ACS Catalysis,2013,vol. 3,p. 2076 - 2082

62
[ 78191-00-1 ]
[ 95-54-5 ]
[ 615-15-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With boron trifluoride diethyl etherate; In 1,4-dioxane; at 20 - 100℃; for 1h;Inert atmosphere;	General procedure: To a solution of o-diaminobenzene (5.0 mmol, 0.5405 g) and Weinreb amide (N-methoxy-Nmethylbenzamide, 5.0 mmol, 0.82595 g) in dioxane (10 mL), boron trifluoride diethyl etherate (5.0 mmol) was added at room temperature. The reaction mixture was stirred for the specified time (Table 3) at 100 °C. TLC revealed the complete consumption of starting material. Subsequently hydrolysis was achieved by the addition of saturated NH4Cl solution (50 mL). The aqueous layer was extracted with ethyl acetate (3 X 25 mL), washed with water (2 X 25 mL), brine solution (2 X 25 mL), dried over anhydrous Na2SO4 and concentrated under vacuum to get crude product. This was purified by column chromatography over silica gel using hexane/ethyl acetate mixture in 1:1 ratios as eluent.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2693 - 2695

63
[ 615-15-6 ]
[ 146137-78-2 ]
[ 1446741-55-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3794 - 3797

64
[ 615-15-6 ]
[ 146137-79-3 ]
[ 1446741-58-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3794 - 3797

65
[ 93249-44-6 ]
[ 615-15-6 ]
[ 1446741-59-8 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3794 - 3797

66
[ 615-15-6 ]
[ 40273-47-0 ]
[ 109095-61-6 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3794 - 3797

67
[ 615-15-6 ]
[ 89-60-1 ]
[ 1449333-21-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4218 - 4221

68
[ 615-15-6 ]
[ 41042-12-0 ]
C₁₉H₁₉N₃O₂ [ No CAS ]

Reference： [1]RSC Advances,2013,vol. 3,p. 20281 - 20286

69
[ 615-15-6 ]
[ 652-36-8 ]
3C₈H₂F₄O₄*3C₈H₈N₂ [ No CAS ]

Reference： [1]CrystEngComm,2014,vol. 16,p. 4142 - 4161

70
[ 615-15-6 ]
[ 7310-97-6 ]
[ 1616390-03-4 ]

Reference： [1]New Journal of Chemistry,2014,vol. 38,p. 3042 - 3049
[2]Tetrahedron,2017,vol. 73,p. 2886 - 2893
[3]Journal of Photochemistry and Photobiology A: Chemistry,2018,vol. 364,p. 705 - 714

71
[ 615-15-6 ]
[ 32710-65-9 ]
2-(2-methyl-1H-benzimidazol-1-yl)-6-[4-(trifluoromethyl)phenyl]amino}pyridine-4-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2015/76800,2015,A1

72
[ 615-15-6 ]
[ 32710-65-9 ]
2-chloro-6-(2-methyl-1H-benzo[d]imidazol-1-yl)isonicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 20h;	Step 1. To <strong>[32710-65-9]2,6-dichloroisonicotinonitrile</strong> (567 mg, 3.33. mmol) was added 2- methyl-lH-benzo[d]imidazole (660 mg, 5 mmol), DMF (3 mL) and KOi-Bu (1M solution in THF, 3.3 mL, 3.3 mmol) at room temperature. The mixture was reacted at room temperature for 20 hours. The reaction was quenched with AcOH, then partitioned between water and a mixture of EtOAc:hexane. The organic layer was purified by chromatography on silica gel (gradient ethyl acetate :hexane 1 :2 to 1 :0) to provide 2-chloro-6-(2-methyl- lH- benzo[d]imidazol- l-yl)isonicotinonitrile as a pink solid (402 mg, 45 %). ]H NMR (DMSO- d6) delta 8.34 (distd(AB), J = 0.9 Hz, 1H), 8.33 (dist.d(AB), J = 0.9 Hz, 1H), 7.64 - 7.67 (m, 1H), 7.57 - 7.60 (m, 1H), 7.26 - 7.31 (m, 2H), 2.64 (s, 3H).

Reference： [1]Patent: WO2015/76800,2015,A1 .Location in patent: Page/Page column 238

73
[ 615-15-6 ]
[ 42521-09-5 ]
methyl 2-chloro-6-(2-methyl-1H-benzo[d]imidazol-1-yl)isonicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 72h;	Step 1. To <strong>[42521-09-5]methyl 2,6-dichloroisonicotinate</strong> (1.54 g, 7.5 mmol) was added 2- methyl-lH-benzo[d]imidazole (0.66 g, 5 mmol), DMF (10 mL) and KOi-Bu (1M solution on THF, 5 mL, 5 mmol). The mixture was reacted at room temperature for 3 days, diluted with aqueous ammonium chloride, then filtered and purified by chromatography on silica gel (gradient ethyl acetate :hexane 1:4 to 1:0) to provide crude methyl 2-chloro-6-(2-methyl-lH- benzo[d]imidazol-l-yl)isonicotinate (96 mg).

Reference： [1]Patent: WO2015/76800,2015,A1 .Location in patent: Page/Page column 242

74
[ 615-15-6 ]
[ 35730-09-7 ]
[ 912577-90-3 ]

Yield	Reaction Conditions	Operation in experiment
9.66 g	Stage #1: 2-Methyl-1H-benzimidazole; 2,5-difluorobenzoyl chloride With triethylamine In tetrahydrofuran at 50 - 70℃; for 3h; Inert atmosphere; Stage #2: With morpholine In tetrahydrofuran at 20 - 70℃; for 2h;	1 Production of 1-(2,5-Difluorophenyl)-2-(1,3-dihydro-2H-benzoimidazol-2-ylidene)ethanone [0078] Under a nitrogen atmosphere, to a solution of 5.0 g of 2-methyl-1H-benzoimidazole and 12.44 g of triethylamine in THF (60 mL) was added 21.37 g of 2,5-difluorobenzoyl chloride at an inner temperature of 50°C or lower, followed by stirring at an inner temperature of 60°C to 70°C for 3 hours. The reaction mixture was cooled to an inner temperature of 20°C to 30°C, and then 6.92 g of morpholine was added thereto at an inner temperature of 20°C to 50°C, followed by stirring at an inner temperature of 60°C to 70°C for 2 hours. 90 mL of water and 60 mL of MeCN were each added dropwise thereto over 30 minutes at an inner temperature of 40°C to 50°C, followed by stirring at the same temperature for 1 hour. Thereafter, the mixture was cooled to an inner temperature of 0°C to 10°C for 1 hour or longer and stirred at the same temperature for 12 hours, and then the precipitated crystal was collected by filtration and washed sequentially with 15 mL of an MeCN/water mixed solution (2/1 (v/v)) and 25 mL of water. [0079] The obtained crystal was suspended in 25 mL of MeCN and 50 mL of water, followed stirring at an inner temperature of 40°C to 50°C for 30 minutes and then stirring at an inner temperature of 20°C to 30°C for 1 hour. The crystal was collected by filtration, then washed with 25 mL of an MeCN/water mixed solution (17/33 (v/v)) and dried at 60°C overnight under reduced pressure to obtain 9.66 g of 1-(2,5-difluorophenyl)-2-(1,3-dihydro-2H-benzoimidazol-2-ylidene)ethanone as a crystal. [0080] The physicochemical data of the obtained compound are shown below. [0081] 1H-NMR (DMSO-d6, 400 MHz): δ (ppm)=5.91 (1H, s), 7.11-7.16 (2H, m), 7.21-7.38 (4H, m), 7.53 (1H, brs), 7.55-7.61 (1H, m), 12.29 (1H, brs) [0082] ESI-MS: m/z = 273 ([M+H]+)
9.66 g	Stage #1: 2-Methyl-1H-benzimidazole; 2,5-difluorobenzoyl chloride With triethylamine In tetrahydrofuran at 50 - 70℃; for 3h; Inert atmosphere; Stage #2: With morpholine In tetrahydrofuran at 20 - 70℃; for 2h;	1 Preparation Example 1Production of 1 -(2,5-Difluorophenyl)-2-(1 ,3-dihy- dro-2H-benzoimidazol-2-ylidene)ethanone 10122] Under a nitrogen atmosphere, to a solution of 5.0 g of 2-methyl- 1H-benzoimidazole and 12.44 g of triethylamine in THF (60 mE) was added 21.37 g of 2,5-difluorobenzoyl chloride at an inner temperature of 50° C. or lower, followed by stirring at an inner temperature of 60° C. to 70° C. for 3 hours. The reaction mixture was cooled to an inner temperature of 20° C. to 30° C., and then 6.92 g ofmorpholine was added thereto at an inner temperature of 20° C. to 50° C., followed by stirring at an innertemperature of 60°C. to 70° C. for 2 hours. 90 mE of water and 60 mE of MeCN were each added dropwise thereto over 30 minutes at an inner temperature of 40° C. to 50° C., followed by stirring at the same temperature for 1 hour. Thereafier, the mixture was cooled to an inner temperature of 0° C. to 10°C. for 1 hour or longer and stirred at the same temperature for 12 hours, and then the precipitated crystal was collected by filtration and washed sequentially with 15 mE of an MeCN/water mixed solution (2/1 (v/v)) and 25 mE of watet10123] The obtained crystal was suspended in 25 mE of MeCN and 50 mE of water, followed stirring at an inner temperature of 40° C. to 50° C. for 30 minutes and then stirring at an inner temperature of 20° C. to 30° C. for 1 hout The crystal was collected by filtration, then washed with 25 mE of an MeCN/water mixed solution (17/33 (v/v)) and dried at 60° C. overnight under reduced pressure to obtain 9.66 g of 1 -(2,5-difluorophenyl)-2-(1 ,3-dihydro-2H-benzoimidazol-2-ylidene)ethanone as a crystal.10124] The physicochemical data of the obtained compound are shown below.10125] ‘H-NMR (DMSO-d6, 400 MHz): ö (ppm)=5.91 (1H, s), 7.11-7.16 (2H, m), 7.21-7.38 (4H, m), 7.53 (1H, brs), 7.55-7.61 (1H, m), 12.29 (1H, brs)10126] ESI-MS: mlz=273 ([M+H])

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - EP2894152, 2015, A1 Location in patent: Paragraph 0078; 0079; 0080; 0081; 0082
[2]Current Patent Assignee: ASTELLAS PHARMA INC. - US2015/259299, 2015, A1 Location in patent: Paragraph 0122; 0123; 0124; 0125; 0126

75
[ 615-15-6 ]
[ 41042-12-0 ]
[ 109-77-3 ]
C₂₂H₁₉N₅O [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 81103 - 81107

76
[ 615-15-6 ]
[ 1761-56-4 ]
[ 6018-89-9 ]
[Ni(2-((2-oxybenzylidene)amino)phenolate)(2-Me-benzimidazole)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In methanol; acetonitrile; for 2h;Reflux;	General procedure: We added a solution of nickel(II) acetate tetrahydrate (0.497g; 0.002mol) in MeOH (30mL) and solid PPh3 (0.524g; 0.002mol) to a solution of Schiff base H2L (0.426g; 0.002mol) in MeCN (30mL). The resulting solution was refluxed for 2h and then left to evaporate slowly at ambient temperature. Well shaped red-brown crystals of complex 5a suitable for single crystal X-ray structure analysis were collected after few days by filtration, washed with methanol and finally dried at ambient temperature.

Reference： [1]Polyhedron,2016,vol. 117,p. 90 - 96

77
[ 615-15-6 ]
[ 570-22-9 ]
[ 5313-35-9 ]

Yield	Reaction Conditions	Operation in experiment
< 1%; 78%	With sulfuric acid; dihydrogen peroxide; In water; at 100 - 130℃;	General procedure: A solution of 10.0 mmol of compound 1a-1d in 14 mL of concentrated sulfuric acid was heated to 100-105C, 14 mL (0.26 mol) of 30% aqueous hydrogen peroxide was added dropwise with stirring,and the mixture was stirred for 1 h at 130C. After cooling, the mixture was poured into water and adjusted to pH 4, and the precipitate was filtered off.

Reference： [1]Russian Journal of Organic Chemistry,2016,vol. 52,p. 1528 - 1530
Zh. Org. Khim.,2016,vol. 52,p. 1533 - 1535,3

78
[ 615-15-6 ]
[ 3939-13-7 ]
5-aminobenzimidazo[1,2-a][1,8]naphthyridine [ No CAS ]