[ CAS No. 10394-38-4 ] {[proInfo.proName]}

Name: 10394-38-4|1-Methylbenzoimidazol-5-amine|97%
Brand: Ambeed
SKU: A318640
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Quality Control of [ 10394-38-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 10394-38-4 ]

Product Details of [ 10394-38-4 ]

CAS No. :	10394-38-4	MDL No. :	MFCD03164349
Formula :	C₈H₉N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IWBGBYZGEQUDBT-UHFFFAOYSA-N
M.W :	147.18	Pubchem ID :	315499
Synonyms :

Calculated chemistry of [ 10394-38-4 ]

Physicochemical Properties

Num. heavy atoms :	11
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 :	45.4
TPSA :	43.84 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) :	-6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.17
Log Po/w (XLOGP3) :	0.76
Log Po/w (WLOGP) :	1.16
Log Po/w (MLOGP) :	0.7
Log Po/w (SILICOS-IT) :	0.71
Consensus Log Po/w :	0.9

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	2.14 mg/ml ; 0.0146 mol/l
Class :	Very soluble
Log S (Ali) :	-1.26
Solubility :	8.08 mg/ml ; 0.0549 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.09
Solubility :	1.19 mg/ml ; 0.00807 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.43

Safety of [ 10394-38-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 10394-38-4 ]

* 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 [ 10394-38-4 ]
Downstream synthetic route of [ 10394-38-4 ]

[ 10394-38-4 ] Synthesis Path-Upstream 1~14

1
[ 5381-78-2 ]
[ 10394-38-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In ethanol at 20℃; for 18 h;	Example B23 1-Methyl-5-nitro-1H-benzo[d]imidazole (prepared as described in WO 2005/092899; 1.14 g, 6.43 mmol) in EtOH (50 ml) was stirred under H₂ (1 atm) at RT in the presence of 10percent Pd/C (50 wt percent H₂O, 1.37 g, 0.643 mmol). After 18 h, the completed reaction was filtered on Celite, rinsing forward with EtOH. The combined filtrates were concentrated to afford crude 1-methyl-1H-benzo[d]imidazol-5-amine (1.02 g, 108percent yield) as a dark orange oil which was used as is in the next reaction. ¹H NMR (400 MHz, DMSO-d₆) δ 7.87 (s, 1H), 7.17 (d, J=8.4 Hz, 1H), 6.75 (d, J=2.0 Hz, 1H), 6.59 (dd, J=2.0 and 8.4 Hz, 1H), 4.73 (brs, 2H), 3.69 (s, 3H); MS (ESI) m/z: 148.0 (M+H⁺). Using a procedure analogous to Example B22, 1-methyl-1H-benzo[d]imidazol-5-amine (0.50 g, 3.4 mmol), NaNO₂ (0.28 g, 4.1 mmol), SnCl₂.2H₂O (2.8 g, 14 mmol) and 4-methyl-3-oxopentanenitrile (0.45 g, 4.1 mmol) were combined to afford crude 3-isopropyl-1-(1-methyl-1H-benzo[d]imidazol-5-yl)-1H-pyrazol-5-amine (0.63 g, 73percent yield) as a foam which was used as is in the next reaction. ¹H NMR (400 MHz, DMSO-d₆): δ 8.22 (s, 1H), 7.72 (dd, J=0.40 and 1.2 Hz, 1H), 7.60 (dd, J=0.40 and 8.4 Hz, 1H), 7.42 (dd, J=2.0 and 8.4 Hz, 1H), 5.32 (s, 1H), 5.08 (brs, 2H), 3.85 (s, 3H), 2.75 (septet, J=6.8 Hz, 1H), 1.16 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 250.0 (M+H⁺).
76%	With hydrogen In toluene at 40℃; for 4 h;	Step 1 To a solution of 1-Methyl-5-nitro-1H-benzoimidazole (3.4 g, 19.2 mmol) in toluene (75 mL) was added Raney Nickel (1 g). The mixture was stirred at 40° C. under H₂for 4 h. The reaction mixture was filtered though celite and concentrated in vacuo to give an orange solid. The crude solid was purified by silica gel chromatography (40-65percent EtOAc/Hexanes) to give the desired amine as an orange solid (2.14 g, 76percent). ¹H-NMR (400 MHz, CDCl₃): δ 7.77 (s, 1H), 7.22 (d, 1H), 6.93 (s, 1H), 6.88 (dd, 1H), 4.01 (s, 3H), 3.60 (s, 2H).

Reference： [1] Patent: US2008/90856, 2008, A1, . Location in patent: Page/Page column 46-47
[2] Patent: US2007/27184, 2007, A1, . Location in patent: Page/Page column 20
[3] Journal of Pharmacy and Pharmacology, 1951, vol. 3, p. 420,424
[4] Gazzetta Chimica Italiana, 1955, vol. 85, p. 981,984
[5] Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 3, p. 713 - 724
[6] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 9, p. 897 - 902
[7] Magnetic Resonance in Chemistry, 2009, vol. 47, # 2, p. 100 - 104
[8] Patent: WO2013/36232, 2013, A2, . Location in patent: Paragraph 00338
[9] Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 5, p. 1343 - 1348

2
[ 5381-79-3 ]
[ 5381-78-2 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Yield	Reaction Conditions	Operation in experiment
45%	With 10% palladium on activated carbon; Degussa type; hydrogen In methanol at 20℃; for 2 h;	General procedure: Procedure B: The nitro-group containing compound was dissolved in MeOH (or a mixture of MeOH and tetrahydrofuran) and then 10percent Pd/C was added. The mixture was stirred at room temperature under hydrogen gas until the starting material had been consumed. The crude mixture was filtered through Celite, washed with methanol, and then concentrated. The product was carried on to the next step without further purification or was purified by column chromatography.

Reference： [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830

3
[ 94-52-0 ]
[ 74-88-4 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Reference： [1] Patent: WO2017/153952, 2017, A1, . Location in patent: Page/Page column 238

4
[ 5381-79-3 ]
[ 5381-78-2 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Reference： [1] Patent: WO2006/123145, 2006, A1, . Location in patent: Page/Page column 53

5
[ 51-17-2 ]
[ 74-88-4 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Reference： [1] Russian Journal of Organic Chemistry, 2017, vol. 53, # 4, p. 547 - 549[2] Zh. Org. Khim., 2017, vol. 53, # 4, p. 541 - 544

6
[ 53484-15-4 ]
[ 10394-38-4 ]

Reference： [1] Patent: WO2016/57834, 2016, A1, . Location in patent: Paragraph 000388

7
[ 1632-83-3 ]
[ 10394-38-4 ]

Reference： [1] Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 5, p. 1343 - 1348

8
[ 95-54-5 ]
[ 10394-38-4 ]

Reference： [1] Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 5, p. 1343 - 1348

9
[ 51-17-2 ]
[ 10394-38-4 ]

Reference： [1] Journal of the Chemical Society of Pakistan, 2013, vol. 35, # 5, p. 1343 - 1348

10
[ 41939-61-1 ]
[ 10394-38-4 ]

Reference： [1] Journal of Pharmacy and Pharmacology, 1951, vol. 3, p. 420,424

11
[ 5381-79-3 ]
[ 5381-78-2 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Yield	Reaction Conditions	Operation in experiment
45%	With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2 h;	General procedure: Procedure B: The nitro-group containing compound was dissolved in MeOH (or a mixture of MeOH and tetrahydrofuran) and then 10percent Pd/C was added. The mixture was stirred at room temperature under hydrogen gas until the starting material had been consumed. The crude mixture was filtered through Celite, washed with methanol, and then concentrated. The product was carried on to the next step without further purification or was purified by column chromatography.

Reference： [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830

12
[ 94-52-0 ]
[ 74-88-4 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Reference： [1] Patent: WO2017/153952, 2017, A1, . Location in patent: Page/Page column 238

13
[ 5381-79-3 ]
[ 5381-78-2 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Reference： [1] Patent: WO2006/123145, 2006, A1, . Location in patent: Page/Page column 53

14
[ 51-17-2 ]
[ 74-88-4 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Reference： [1] Russian Journal of Organic Chemistry, 2017, vol. 53, # 4, p. 547 - 549[2] Zh. Org. Khim., 2017, vol. 53, # 4, p. 541 - 544

[ 10394-38-4 ] Synthesis Path-Downstream 1~52

1
[ 5381-78-2 ]
[ 10394-38-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 18h;	Example B23 1-Methyl-5-nitro-1H-benzo[d]imidazole (prepared as described in WO 2005/092899; 1.14 g, 6.43 mmol) in EtOH (50 ml) was stirred under H2 (1 atm) at RT in the presence of 10% Pd/C (50 wt % H2O, 1.37 g, 0.643 mmol). After 18 h, the completed reaction was filtered on Celite, rinsing forward with EtOH. The combined filtrates were concentrated to afford crude 1-methyl-1H-benzo[d]imidazol-5-amine (1.02 g, 108% yield) as a dark orange oil which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6) delta 7.87 (s, 1H), 7.17 (d, J=8.4 Hz, 1H), 6.75 (d, J=2.0 Hz, 1H), 6.59 (dd, J=2.0 and 8.4 Hz, 1H), 4.73 (brs, 2H), 3.69 (s, 3H); MS (ESI) m/z: 148.0 (M+H+). Using a procedure analogous to Example B22, 1-methyl-1H-benzo[d]imidazol-5-amine (0.50 g, 3.4 mmol), NaNO2 (0.28 g, 4.1 mmol), SnCl2.2H2O (2.8 g, 14 mmol) and 4-methyl-3-oxopentanenitrile (0.45 g, 4.1 mmol) were combined to afford crude 3-isopropyl-1-(1-methyl-1H-benzo[d]imidazol-5-yl)-1H-pyrazol-5-amine (0.63 g, 73% yield) as a foam which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): delta 8.22 (s, 1H), 7.72 (dd, J=0.40 and 1.2 Hz, 1H), 7.60 (dd, J=0.40 and 8.4 Hz, 1H), 7.42 (dd, J=2.0 and 8.4 Hz, 1H), 5.32 (s, 1H), 5.08 (brs, 2H), 3.85 (s, 3H), 2.75 (septet, J=6.8 Hz, 1H), 1.16 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 250.0 (M+H+).
76%	With hydrogen;Raney nickel; In toluene; at 40℃; for 4h;	Step 1 To a solution of 1-Methyl-5-nitro-1H-benzoimidazole (3.4 g, 19.2 mmol) in toluene (75 mL) was added Raney Nickel (1 g). The mixture was stirred at 40 C. under H2 for 4 h. The reaction mixture was filtered though celite and concentrated in vacuo to give an orange solid. The crude solid was purified by silica gel chromatography (40-65% EtOAc/Hexanes) to give the desired amine as an orange solid (2.14 g, 76%). 1H-NMR (400 MHz, CDCl3): delta 7.77 (s, 1H), 7.22 (d, 1H), 6.93 (s, 1H), 6.88 (dd, 1H), 4.01 (s, 3H), 3.60 (s, 2H).
	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 18h;	l -Methyl-5-nitro-lH-benzo[d]imidazole (prepared as described in WO 2005/092899; 1.14 g, 6.43 mmol) in EtOH (50 ml) was stirred under H2 (1 atm) at RT in the presence of 10% Pd/C (50 wt% H20, 1.37 g, 0.643 mmol). After 18 h, the completed reaction was filtered on Celite, rinsing forward with EtOH. The combined filtrates were concentrated to afford crude 1 -methyl- lH-benzo[d]imidazol-5- amine (1.02 g, 108% yield) as a dark orange oil which was used as is in the next reaction. FontWeight="Bold" FontSize="10" H NMR (400 MHz, DMSO-i delta 7.87 (s, 1H), 7.17 (d, J = 8.4 Hz, 1H), 6.75 (d, J = 2.0 Hz, 1H), 6.59 (dd, J = 2.0 and 8.4 Hz, 1H), 4.73 (brs, 2H), 3.69 (s, 3H); MS (ESI) m/z: 148.0 (M+H+).

Reference： [1]Patent: US2008/90856,2008,A1 .Location in patent: Page/Page column 46-47
[2]Patent: US2007/27184,2007,A1 .Location in patent: Page/Page column 20
[3]Journal of Pharmacy and Pharmacology,1951,vol. 3,p. 420,424
[4]Gazzetta Chimica Italiana,1955,vol. 85,p. 981,984
[5]Collection of Czechoslovak Chemical Communications,1989,vol. 54,p. 713 - 724
[6]Bulletin de la Societe Chimique de France,1996,vol. 133,p. 897 - 902
[7]Magnetic Resonance in Chemistry,2009,vol. 47,p. 100 - 104
[8]Patent: WO2013/36232,2013,A2 .Location in patent: Paragraph 00338
[9]Journal of the Chemical Society of Pakistan,2013,vol. 35,p. 1343 - 1348

2
[ 10394-38-4 ]
[ 1147550-11-5 ]
[ 58687-47-1 ]

Reference： [1]Pharmaceutical Chemistry Journal,1976,vol. 9,p. 759 - 763

3
[ 10394-38-4 ]
[ 87-13-8 ]
[ 119199-00-7 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2640 - 2645

4
[ 10394-38-4 ]
[ 73857-60-0 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 62 - 66
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 74 - 78

5
[ 10394-38-4 ]
[ 88-65-3 ]
N-(1-methyl-indazol-5-yl)anthranilic acid [ No CAS ]

Reference： [1]Synthetic Communications,1995,vol. 25,p. 2443 - 2448

6
[ 10394-38-4 ]
[ 33884-41-2 ]
3-[(1-Methyl-1H-benzoimidazol-5-ylamino)-methylene]-pentane-2,4-dione [ No CAS ]

Reference： [1]Bulletin de la Societe Chimique de France,1996,vol. 133,p. 897 - 902

7
[ 10394-38-4 ]
[ 49836-24-0 ]
2-[1-(1-Methyl-1H-benzoimidazol-5-ylamino)-meth-(Z)-ylidene]-3-oxo-butyric acid ethyl ester [ No CAS ]

Reference： [1]Bulletin de la Societe Chimique de France,1996,vol. 133,p. 897 - 902

8
[ 10394-38-4 ]
[ 186341-01-5 ]
2-[1-(1-Methyl-1H-benzoimidazol-5-ylamino)-meth-(E)-ylidene]-3-oxo-butyronitrile [ No CAS ]

Reference： [1]Bulletin de la Societe Chimique de France,1996,vol. 133,p. 897 - 902

9
[ 10394-38-4 ]
[ 137024-37-4 ]
2-[1-(1-Methyl-1H-benzoimidazol-5-ylamino)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester [ No CAS ]

Reference： [1]Bulletin de la Societe Chimique de France,1996,vol. 133,p. 897 - 902

12
[ 10394-38-4 ]
N-(1-methylbenzimidazol-5-yl)-5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		10.2 N-(1-methyl-benzimidazol-5-yl)-5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide A solution of 0.32 g (0.95 mmol) of 5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylic acid, obtained in step 10.1, and 0.69 ml (9.49 mmol) of thionyl chloride in 25 ml of dichloromethane is refluxed for 2 hours. The mixture is concentrated under reduced pressure, the residue is taken up in 20 ml of diethyl ether, and 0.17 g (1.14 mmol) of <strong>[10394-38-4]5-amino-1-methylbenzimidazole</strong> and a solution of 0.2 g (1.9 mmol) of sodium carbonate in 2 ml of water are added. The mixture is stirred for 24 hours at room temperature, the organic phase is evaporated under reduced pressure and the resulting phase is extracted with ethyl acetate and dichloromethane. The organic phases are washed with water and with saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue is taken up in petroleum ether, collected by filtration, washed and dried under reduced pressure. It is then purified by chromatography on a column of silica gel, eluding with a mixture of dichloromethane and ethyl acetate. The residue is taken up in petroleum ether, collected by filtration, washed and dried under reduced pressure. 0.3 g of solid is obtained. Melting point: 223-224 C. 1H NMR (DMSO), delta (ppm): 5.9 (s, 2H); 7 (m, 3H); 7.3 (m, 1H); 7.55 (m, 4H); 7.8 (d, 1H); 8.05 (s, 1H); 8.1 (d, 2H); 10.5 (s, 1H).

Reference： [1]Patent: US2007/259946,2007,A1 .Location in patent: Page/Page column 12

13
[ 1009330-41-9 ]
[ 10394-38-4 ]
C₁₉H₁₇N₇O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4363 - 4368

14
[ 10394-38-4 ]
[ 73857-49-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 62 - 66
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 74 - 78

15
[ 10394-38-4 ]
[ 73857-50-8 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 62 - 66
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 74 - 78

16
[ 10394-38-4 ]
[ 128056-61-1 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2640 - 2645

17
[ 10394-38-4 ]
[ 128056-54-2 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2640 - 2645

18
[ 41939-61-1 ]
[ 10394-38-4 ]

Reference： [1]Journal of Pharmacy and Pharmacology,1951,vol. 3,p. 420,424

19
[ 10394-38-4 ]
[ 335439-70-8 ]
3-[2-(2,4-dichloro-phenyl)-ethoxy]-4-methoxy-N-(1-methyl-1H-benzoimidazol-5-yl)-benzamide [ No CAS ]

Reference： [1]Patent: EP1217000,2002,A1 .Location in patent: Page 45

20
[ 10394-38-4 ]
3-methylamino-3-(pyridin-4-yl)-acrylic acid ethyl ester [ No CAS ]
3-(1-methyl-1H-benzimidazol-5-yl-amino)-3-(pyridin-4-yl)-acrylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: WO2004/89950,2004,A1 .Location in patent: Page/Page column 11

21
[ 10394-38-4 ]
1-Methyl-4-bromo-5-aminobenzimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.27 g (1.2 mmol, 50%)	With bromine; In methanol; acetic acid;	1-Methyl-4-bromo-5-aminobenzimidazole. To a solution of <strong>[10394-38-4]1-methyl-5-aminobenzimidazole</strong> (0.36 g, 2.4 mmol) in 10 ml of AcOH was added Br2 (0.12 ml). The reaction mixture was stirred for 1 h at 25 C. and concentrated in vacuo, yielding an oil which was subjected to column chromatography (NH3 sat'd 3% MeOH/CHCl3) to yield 0.27 g (1.2 mmol, 50%) of the desired product.

Reference： [1]Patent: US6316637,2001,B1

22
[ 10394-38-4 ]
[ 920978-85-4 ]
[ 920978-57-0 ]

Yield	Reaction Conditions	Operation in experiment
		2.4 N-(1-methyl-1H-benzimidazol-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (compound 2); 0.3 g (2.05 mmol) of <strong>[10394-38-4]5-amino-1-methylbenzimidazole</strong> and 10 ml of dry toluene are placed, under a stream of nitrogen, in a 100 ml three-necked flask cooled to 0 C. and equipped with a magnetic stirrer. 1.58 ml (3.16 mmol) of a 2M solution of trimethylaluminum in toluene are then added slowly to this solution. The reaction mixture obtained is maintained under a nitrogen atmosphere and stirred while allowing the temperature to rise gradually to 70 C. A solution of 0.5 g (1.58 mmol) of product obtained in step 2.3 in 10 ml of dry toluene is then added dropwise over 5 minutes, via an addition funnel. The reaction mixture is then refluxed for 2 hours. 10 ml of 1 N hydrochloric acid and 20 ml of ice-water are then added to the solution cooled to 0 C. After stirring for 1 hour at room temperature, the precipitate formed is collected by filtration, washed with water, dried under reduced pressure and recrystallized from isopropanol. The expected product is isolated in the form of a yellow solid.Melting point: 279-281 C.1H NMR (DMSO D6), delta (ppm): 10.6 (s, 1H); 8.65 (s, 1H); 8.15 (s, 1H); 8.05 (s, 1H); 7.65 (m, 2H); 7.35 (m, 3H); 6.99 (m, 3H); 5.9 (s, 2H); 3.9 (s, 3H).

Reference： [1]Patent: US2008/125459,2008,A1 .Location in patent: Page/Page column 9

23
[ 10394-38-4 ]
[ 920978-96-7 ]
[ 920978-70-7 ]

Yield	Reaction Conditions	Operation in experiment
		12.5 N-(1-methyl-1H-benzimidazol-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide; 0.18 g (1.23 mmol) of <strong>[10394-38-4]5-amino-1-methylbenzimidazole</strong> and 10 ml of dry toluene are placed, while flushing with nitrogen, in a 100 ml three-necked flask cooled to 0 C. and equipped with a magnetic stirrer. To this solution is then added slowly 0.95 ml (1.90 mmol) of a 2M solution of trimethylaluminum in toluene. The reaction mixture obtained is maintained under a nitrogen atmosphere and stirred, while allowing the temperature to rise gradually to 70 C. A solution of 0.3 g (0.95 mmol) of product obtained in step 12.4 in 10 ml of dry toluene is then added dropwise over 5 minutes using an addition funnel. The reaction mixture is then refluxed for 5 hours and stirred at room temperature overnight. 20 ml of cold water are then added to the solution cooled to 0 C., followed by addition of 10 ml of 1N hydrochloric acid. After stirring for 1 hour, the precipitate is recovered by filtration, rinsed with water and dried under reduced pressure. 0.22 g (0.53 mmol) of the expected product is obtained in the form of a white solid.Melting point: 266-268 C.1H NMR (DMSO D6), delta (ppm): 9.5 (s, 1H); 8.5 (s, 1H); 7.9 (s, 2H); 7.5 (m, 3H); 7.3-6.8 (m, 5H); 5.9 (s, 2H); 3.95 (s, 3H).

Reference： [1]Patent: US2008/125459,2008,A1 .Location in patent: Page/Page column 13

24
[ 10394-38-4 ]
[ 921039-97-6 ]
N-(1-methyl-1H-benzimidazol-5-yl)-5-fluoro-1-[(pyrid-3-yl)methyl]-1H-indole-2-carboxamide dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		2.2 N-(1-Methyl-1H-benzimidazol-5-yl)-5-fluoro-1-[(pyrid-3-yl)methyl]-1H-indole-2-carboxamide hydrochloride (1:2) (Compound 4) 4.1 ml of trimethylaluminum (2M in toluene) are added under argon to a solution of 0.414 g (2.82 mmol) of 5-amino-1-methyl-1H-benzimidazole in 10 ml of dry toluene. After 15 minutes, 0.7 g (2.35 mmol) of ethyl 5-fluoro-1-[(pyrid-3-yl)methyl]-1H-indole-2-carboxylate, obtained in step 2.1, is added. The reaction medium is refluxed for 4 hours and then stirred overnight at room temperature. It is poured onto 100 g of ice and 50 ml of dichloromethane. A suspension is obtained, which is filtered and washed with water and ether. The residue is purified by preparative chromatography on alumina (eluent: dichloromethane/methanol). 0.36 g of a solid is obtained, which is dried under reduced pressure. The resulting solid is taken up in 30 ml of dichloromethane and 0.55 ml of a 4N solution of hydrogen chloride in dioxane is added. The solution is concentrated under reduced pressure and the resulting solid is recrystallized from a mixture of isopropanol and methanol. 0.36 g of the expected product is thus obtained in the form of a hydrochloride. Melting point (2HCl): 268-270 C. 1H NMR (DMSO D6), delta (ppm): 4.03 (s, 3H); 6 (s, 2H); 7.18 (dxd, 1H); 7.56 (dxd, 1H); 7.68 (m, 2H); 7.9 (m, 4H); 8.41 (s, 1H); 8.69 (m, 2H); 9.59 (s, 1H).

Reference： [1]Patent: US2008/146646,2008,A1 .Location in patent: Page/Page column 8

25
[ 10394-38-4 ]
[ 1174116-65-4 ]
[ 1174118-10-5 ]

Yield	Reaction Conditions	Operation in experiment
10%	With potassium hydroxide; In acetone; for 20h;Heating;	36. 6-Ethoxy-N-furan-2-ylmethyl-N'-(1-methyl-1 H-benzoimidazol-5-yl)-[1,3,5]triazine- 2,4-diamine; [0458] A mixture of 2 (508 mg, 2 mmol), aniline (294 mg, 2 mmol), KOH (168 mg, 3 mmol) and acetone (5 mL) was stirred at refluxing for 20 hours, diluted with water, extracted with ethyl acetate. The combined organic phases were concentrated. Purification by column chromatography (silica gel, methanol/ethyl acetate) gave the product (70 mg, 10%)[0459] 1H-NMR (400MHz, DMSO-D6) deltaH: 1.28 (3H, t, J=7.5 Hz), 3.80 (3H, s), 4.30(2H, q, J=7.5 Hz), 4.48 (2H, broad), 6.20-6.40 (1 H, broad, Z/E forms), 6.38 (1 H, broad), 7.44 (1 H, , J=8.5 Hz), 7.53 (1 H, broad), 7.55 (1H, d, J=1.8 Hz), 7.72 (1 H, broad), 8.10 (1 H, broad), 8.12 (1 H, s), 9.15-9.40 (1 H, broad, Z/E froms). LCMS tR 1.38 (min). MS (APCI), m/z 366.02 [M+H]+. Mp 105-107C

Reference： [1]Patent: WO2009/91388,2009,A2 .Location in patent: Page/Page column 149

26
[ 10394-38-4 ]
[ 35832-93-0 ]
[ 923034-26-8 ]

Yield	Reaction Conditions	Operation in experiment
42%		Step 2 To the product from Step 1 (2.31 g, 15.7 mmol) in water (30 mL) at 0 C. was added conc. HCl (3.14 mL, 37.9 mmol). Sodium nitrite (1.16 g, 16.8 mmol) in water (5 mL) was added portionwise to the stirring solution of amine over a period of 30 minutes. The reaction was stirred at 0 C. for an additional 25 minutes and then added portionwise to a stirring 40-45 C. solution of potassium ethyl xanthate (2.93 g, 18.3 mmol) in water (10 mL). The reaction was stirred at 45 C. for an additional 30 minutes and then cooled to room temperature. The mixture was extracted with Et2O (2×75 mL). The organic extracts were concentrated in vacuo to give a yellow oil. The crude oil was purified by silica gel chromatography to give the desired xanthate ester as a yellow oil (1.68 g, 42%). 1H-NMR (400 MHz, CDCl3): delta 8.02 (s, 1H), 7.90 (s, 1H), 7.45 (m, 2H), 4.62 (q, 2H), 4.11 (s, 3H), 1.33 (t, 3H).

Reference： [1]Patent: US2007/27184,2007,A1 .Location in patent: Page/Page column 20

27
[ 10394-38-4 ]
[ 90-02-8 ]
[ 332886-13-2 ]

Reference： [1]Asian Journal of Chemistry,2012,vol. 24,p. 4449 - 4452

28
[ 10394-38-4 ]
[ 708-06-5 ]
1-[(1-methyl-benzimidazol-5-yl)imino]methyl}naphthalen-2-ol [ No CAS ]

Reference： [1]Asian Journal of Chemistry,2012,vol. 24,p. 4449 - 4452

29
[ 10394-38-4 ]
[ 1403888-69-6 ]
[ 1403886-17-8 ]

Reference： [1]Patent: WO2012/143143,2012,A1

30
[ 10394-38-4 ]
[ 1403888-69-6 ]
C₂₇H₂₄N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In 1,4-dioxane; methanol; at 140℃; for 0.0833333h;Microwave irradiation;	Example No. 126Preparation of (8-Methoxy-2H-pyrazolo [3 , 4-c] quinolin-4-yl) - (1- methyl-lH-benzoimidazol-5-yl) -amine4-chloro-8-methoxy-2- (4-methoxybenzyl) -2H-pyrazolo [3,4- cjquinoline (0.16 mmol) and l-methyl-lH-benzoimidazol-5-amine (2 eq.,0.3 mmol) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HC1 in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was concentrated and purified by semi- preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 344.1599 g/mol HPLC-MS: analytical method Brt: 1.51 min - found mass: 345.2 (m/z+H)

Reference： [1]Patent: WO2012/143143,2012,A1 .Location in patent: Page/Page column 239-240

31
[ 5381-79-3 ]
[ 5381-78-2 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Yield	Reaction Conditions	Operation in experiment
45%; 40%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 2h;	General procedure: Procedure B: The nitro-group containing compound was dissolved in MeOH (or a mixture of MeOH and tetrahydrofuran) and then 10percent Pd/C was added. The mixture was stirred at room temperature under hydrogen gas until the starting material had been consumed. The crude mixture was filtered through Celite, washed with methanol, and then concentrated. The product was carried on to the next step without further purification or was purified by column chromatography.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3821 - 3830

32
[ 10394-38-4 ]
[ 1442459-00-8 ]
[ 1442459-22-4 ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine; In dichloromethane; acetonitrile; at 0 - 20℃;	General procedure: Procedure A: The isothiocyanate compound (1 equiv) was added to the solution of amine (1 equiv) in 5 ml of a mixture of dichloromethane and acetonitrile (1:1, v/v). The mixture was cooled to 0C. Then, triethylamine (2 equiv) was added gradually. The mixture was stirred at 0C for 15 min, after which stirring was continued at room temperature for 2-10 h. The reaction mixture was concentrated, extracted with dichloromethane, and washed with brine.The organic layer was dried over MgSO4 and purified by column chromatography (MeOH/CH2Cl2) or by preparative TLC (MeOH/CH2Cl2) to afford the desired product.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3821 - 3830

33
[ 1632-83-3 ]
[ 10394-38-4 ]

Reference： [1]Journal of the Chemical Society of Pakistan,2013,vol. 35,p. 1343 - 1348

34
[ 10394-38-4 ]
[ 135-19-3 ]
5-(2′-hydroxynaphthyl diazo)-1-methylbenzimidazole [ No CAS ]

Reference： [1]Journal of the Chemical Society of Pakistan,2013,vol. 35,p. 1343 - 1348

35
[ 95-54-5 ]
[ 10394-38-4 ]

Reference： [1]Journal of the Chemical Society of Pakistan,2013,vol. 35,p. 1343 - 1348

36
[ 51-17-2 ]
[ 10394-38-4 ]

Reference： [1]Journal of the Chemical Society of Pakistan,2013,vol. 35,p. 1343 - 1348

37
1-(3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)-3-(4-((2-chloropyrimidin-4-yl)oxy)naphthalen-1-yl)urea [ No CAS ]
[ 10394-38-4 ]
[ 1574357-72-4 ]

Yield	Reaction Conditions	Operation in experiment
9%	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60℃; for 16h;	Example 4 1-(3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)-3-(4-((2-((1-methyl-1H-benzo[d]imidazol-5-yl)amino)pyrimidin-4-yl)oxy)naphthalen-1-yl)urea To a solution of Intermediate C1 (155 mg, 80% purity, 0.236 mmol) in DMF (2.0 mL) was added p-TSA.H2O (90 mg, 0.47 mmol) and <strong>[10394-38-4]1-methyl-1H-benzo[d]imidazol-5-amine</strong> (49 mg, 0.33 mmol). The resulting mixture was heated at 60 C. for 16 hr and was then cooled to RT and partitioned between saturated aq. NaHCO3 (40 mL) and EtOAc (25 mL). The organic layer was separated and washed with water (2*50 mL) and brine (50 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 0-30% MeOH in DCM, gradient elution) and by preparative HPLC to afford the title compound, Example 4, as a pale pink solid (15 mg, 9%); Rt 1.96 min (Method 2, acidic); m/z 638 (M+H)+, (ES+); 1H NMR delta: 1.30 (9H, s), 2.39 (3H, s), 3.74 (3H, s), 6.42 (1H, s), 6.46 (1H, d), 7.23-7.31 (2H, over-lapping m), 7.37 (2H, d), 7.40 (1H, d), 7.47 (2H, d), 7.55 (1H, dd), 7.61 (1H, dd), 7.77 (1H, br s), 7.83 (1H, d), 7.88 (1H, d), 8.00 (1H, s), 8.07 (1H, d), 8.36 (1H, d), 8.86 (1H, s), 9.18 (1H, s), 9.42 (1H, s).
15 mg	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60℃; for 16h;	To a solution of Intermediate C1 (155 mg, 80% purity, 0.236 mmol) in DMF (2.0 mL) was added p-TSA. H20 (90 mg, 0.47 mmol) and 1-methyl-1 /-/-benzo[c ]imidazol-5-amine (49 mg, 0.33 mmol). The resulting mixture was heated at 60C for 16 hr and was then cooled to RT and partitioned between saturated aq. NaHC03 (40 mL) and EtOAc (25 mL). The organic layer was separated and washed with water (2 x 50 mL) and brine (50 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 40 g, 0-30% MeOH in DCM, gradient elution) and by preparative HPLC to afford the title compound, Example 4, as a pale pink solid (15 mg, 9%); Rl 1.96 min (Method 2, acidic); m/z 638 (M+H)+ , (ES+); 1 H NMR delta: 1.30 (9H, s), 2.39 (3H, s), 3.74 (3H, s), 6.42 (1 H, s), 6.46 (1 H, d), 7.23-7.31 (2H, over-lapping m), 7.37 (2H, d), 7.40 (1 H, d), 7.47 (2H, d), 7.55 (1 H, dd), 7.61 (1 H, dd), 7.77 (1 H, br s), 7.83 (1 H, d), 7.88 (1 H, d), 8.00 (1 H, s), 8.07 (1 H, d), 8.36 (1 H, d), 8.86 (1 H, s), 9.18 (1 H, s), 9.42 (1 H, s). Example 5: 1 -(4-((2-((3-Aminobenzo[d]isoxazol-5-yl)amino)pyrimidin-4-yl)oxy) naphthalen-1 -yl)-3-(3-(ferf-butyl)-1 -(p-tolyl)-l W-pyrazol-5-yl)urea.

Reference： [1]Patent: US2015/203475,2015,A1 .Location in patent: Paragraph 0565; 0566
[2]Patent: WO2014/33448,2014,A1 .Location in patent: Page/Page column 72

38
[ 10394-38-4 ]
[ 1610766-74-9 ]
[ 1610766-88-5 ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2014,vol. 29,p. 408 - 419

39
[ 10394-38-4 ]
[ 1885-14-9 ]
C₁₅H₁₃N₃O₂ [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2014,vol. 29,p. 408 - 419

40
[ 10394-38-4 ]
[ 1610766-88-5 ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2014,vol. 29,p. 408 - 419

41
[ 10394-38-4 ]
[ 36980-80-0 ]
ethyl 1-(1-methyl-1H-benzimidazol-5-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		1.76 g (6.79 mmol) of ethyl 3-ethoxy-2-[(ethoxycarbonyl)carbamoyl]acrylate and 1.00 g (6.79 mmol) of <strong>[10394-38-4]1-methyl-1H-benzimidazol-5-amine</strong> [for preparation see: US 2008/0090856, Ex. B23] in 51 ml of ethanol were heated to reflux for 2 h. Thereafter, at RT, 0.76 g (6.79 mmol) of potassium tert-butoxide were added and the reaction mixture was heated to reflux for a further 3 h. Water was added, and the reaction mixture was acidified with 1N aqueous hydrochloric acid. The aqueous phase was concentrated, dichloromethane/methanol (1:1) was added and the solid formed was filtered off. The filtrate was concentrated, MTBE/ethyl acetate (1:1) was added, and the solid formed was filtered off, washed with ethyl acetate and then dried at 50 C. under reduced pressure. This gave 1.55 g (73% of theory) of the title compound. LC-MS (Method 4): Rt=1.00 min; MS (ESIpos): m/z=315 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.22 (t, 3H), 4.03 (s, 3H), 4.18 (q, 2H), 7.62-7.68 (m, 1H), 7.94-8.00 (m, 1H), 8.00-8.03 (m, 1H), 8.35 (s, 1H), 9.24 (br.s, 1H), 11.73 (s, 1H).
1.55 g		1.76 g (6.79 mmol) of ethyl 3-ethoxy-2-[(ethoxycarbonyl)carbamoyl]acrylate and 1.00 g (6.79 mmol) of <strong>[10394-38-4]1-methyl-1H-benzimidazol-5-amine</strong> [for preparation see: US 2008/0090856, Ex. B23] in 51 ml of ethanol were heated to reflux for 2 h. Thereafter, at RT, 0.76 g (6.79 mmol) of potassium tert-butoxide were added and the reaction mixture was heated to reflux for a further 3 h. For workup, the reaction mixture was admixed with water and acidified with 1N hydrochloric acid. The aqueous phase was concentrated, dichloromethane/ methanol (1:1) was added and the solid formed was filtered off. The filtrate was concentrated, MTBE/ ethyl acetate (1:1) was added, and the solid formed was filtered off, washed with ethyl acetate and then dried at 50 C. under reduced pressure. This gave 1.55 g (73% of theory) of the title compound. LC-MS (Method 2): Rt=1.00 min; MS (ESIpos): m/z=315 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=1.22 (t, 3H), 4.03 (s, 3H), 4.18 (q, 2H), 7.62-7.68 (m, 1H), 7.94-8.00 (m, 1H), 8.00-8.03 (m, 1H), 8.35 (s, 1H), 9.24 (br.s, 1H), 11.73 (s, 1H).

Reference： [1]Patent: US2016/244415,2016,A1 .Location in patent: Paragraph 0633; 0634; 0635; 0636
[2]Patent: US2015/148340,2015,A1 .Location in patent: Paragraph 0818; 0819; 0820; 0821

42
[ 10394-38-4 ]
[ 36980-80-0 ]
ethyl 1-(1-methyl-1H-benzimidazol-5-yl)-3-[2-methyl-3-(trifluoromethyl)benzyl]-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate [ No CAS ]

Reference： [1]Patent: US2015/148340,2015,A1
[2]Patent: US2016/244415,2016,A1

43
[ 53484-15-4 ]
[ 10394-38-4 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; copper(l) chloride; at 90℃; for 18h;Sealed tube;	[000388j To a stirred solution of compound 1 (1.6 g, 1 eq) in aq. ammonia solution (5 mL), copper chloride (catalytic amount) was added and heated at 90 C in a sealed tube for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated to dryness. The residue was stirred with 20% methanol in dichloromethane and filtered. The filtrate was evaporated under reduced pressure to afford the title compound 2. LCMS (mlz): 148.00 (M + 1).

Reference： [1]Patent: WO2016/57834,2016,A1 .Location in patent: Paragraph 000388
[2]Patent: WO2019/99311,2019,A1
[3]Patent: CN109776522,2019,A

44
[ 5381-79-3 ]
[ 5381-78-2 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In methanol;	Powdered potassium hydroxide (5.1g, 92mmol) was added to a solution of 6-nitro-lH- benzoimidazole (3g, 18.4mmol) in acetone (30ml) in an ice bath and stirred for 30 min. Methyl iodide (1.7ml, 27.6mmol) was added and the reaction mixture was stirred for 3 hr at room temperature. The solvent was evaporated under reduced pressure to give a residue to which was added water and ethyl acetate. The organic layer was separated and washed with water, dried and concentrated to dryness to yield a mixture of 1- methyl-6-nitro-lH-benzoimidazole and l-methyl-5-nitro-lH-benzoimidazole (3.2g, 98percent) as oil. The mixture of isomers (3.2g, 18.07mmol) was dissolved in methanol (50ml) and hydrogenated at atmospheric pressure over 10percent Pd-C (300mg) until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to yield a mixture of l-methyl-lH-benzimidazol-5-yl amine and 3-methyl- 3H-benzimidazol-5-yl amine (2.53g, 95percent) as solid. The mixture was used in the next stage without purification.

Reference： [1]Patent: WO2006/123145,2006,A1 .Location in patent: Page/Page column 53

45
[ 51-17-2 ]
[ 74-88-4 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Yield	Reaction Conditions	Operation in experiment
		Granular tin, 16 g (0.135 mol), was added to 100 mL of concentrated aqueous HCl, and 8.85 g (0.05 mol) of isomer mixture 2/3 was carefully added in portions. The addition of each portion was accompanied by vigorous reaction with strong heat evolution. When the addition was complete, the hot transparent solution was separated by decanting from the tin residue. After cooling, tin salt of 4/5 precipitated and was filtered off and dispersed in 200 mL of propan-2-ol, solid potassium hydroxide was added until weakly alkaline reaction, the precipitate of Sn(OH)2 was filtered off, and the filtrate was evaporated to dryness. The residue, light brown crystals of isomeric amines 4 and 5, was used in the next step without purification. Yield 6.55 g (89percent), mp 113-114°C. IR spectrum, nu, cm?1: 3376 (NH2, asym.), 3203 (NH2, sym.). 1H NMR spectrum, delta, ppm: isomer 4: 3.81 s (3H, NCH3), 6.62 s (2H, NH2), 6.77 d (1H, 6-H, J = 8.4 Hz), 6.86 d (1H, 7-H, J = 8.4 Hz), 7.30 s (1H, 4-H), 8.49 s (1H, 2-H); isomer 5: 3.69 s (3H, NCH3), 6.59 s (2H, NH2), 6.77 s (1H, 7-H), 6.86 d (1H, 5-H, J = 8.4 Hz), 7.38 d (1H, 4-H, J = 8.4 Hz), 8.08 s (1H, 2-H). Found, percent: C 64.95; H 5.91; N 28.67. C8H9N3. Calculated, percent: C 65.29; H 6.16; N 28.55.

Reference： [1]Russian Journal of Organic Chemistry,2017,vol. 53,p. 547 - 549
Zh. Org. Khim.,2017,vol. 53,p. 541 - 544

46
[ 94-52-0 ]
[ 74-88-4 ]
[ 10394-38-4 ]
[ 26530-93-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of NaH (0.883 g) in Nu,Nu-dimethylformamide (DMF) (20 mL) at 0 °C was added 6-nitro-1 H-benzo[d]imidazole (2 g) and methyl iodide (2.3 mL). The reaction mixture was warmed to room temperature for 2 h . The reaction mixture was then poured into ice/water (30 mL). The solid were filtered and dried under reduced pressure to afford a mixture of 1 -methyl-6-nitro-1 H-benzo[d]imidazole and 1 -methyl-5-nitro-1 H- benzo[d]imidazole (1 g) as a yellow solid. LCMS m/z 178.12 (M+H)+. To a suspension of Pd/C (0.601 g, 0.564 mmol) in methanol (20 mL) at room temperature was added the mixture of 1 -methyl-6-nitro-1 H-benzo[d]imidazole and 1 -methyl-5-nitro-1 H- benzo[d]imidazole (1 g). The reaction was placed under hydrogen (1 atm) for 16 h. The reaction mixture was then filtered through a pad of celite and was concentrated to afford a mixture of 1 -methyl-1 Hbenzo[d]imidazol-6-amine and 1 -methyl-1 H-benzo[d]imidazol-5- amine (500 mg) as a brown solid. LCMS m/z 148.0 (M+H)+.

Reference： [1]Patent: WO2017/153952,2017,A1 .Location in patent: Page/Page column 238

47
[ 10394-38-4 ]
[ 401-55-8 ]
ethyl 2-(6-amino-3-methyl-2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-fluoroacetate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4795 - 4806

48
N-(diphenylmethylene)-1-methyl-1H-benzo[d]imidazol-5-amine [ No CAS ]
[ 10394-38-4 ]

Yield	Reaction Conditions	Operation in experiment
47.4%	With hydrogenchloride; In ethyl acetate; at 20℃; for 7h;	A mixture of A-(di phenyl methylene)- -methyl - l //-benzo[i/]i mi dazol-5-amine (0.446 g, 1.43 mmol) in a solution of hydrogen chloride in EtOAc (8 mL, 32 mmol, 4 M) was stirred at rt for 7 h. The reaction solution was washed with water (30 mL x 2), the combined aqueous phases were adjusted to pH = 12 with NaOH powder, the resulting mixture was extracted with a mixed solvent of DCM/MeOH (10/1 (v/v), 100 mL x 4). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/(a solution of ML in MeOH (7M)) (v/v) = 60/1) to give the title compound as a light yellow solid (100 mg, yield 47.4%).MS (ESI, pos.ion) m/z: 148.3 [M+H]+; 1H NMR (400 MHz, CDCl3) d (ppm): 7.72 (s, 1H), 7.16 (d, J= 8.5 Hz, 1H), 7.08 (d, J= 1.9 Hz, 1H), 6.75 (dd, 7 = 8.5, 1.9 Hz, 1H), 3.77 (s, 3H).
100 mg	With hydrogenchloride; In ethyl acetate; at 20℃; for 7h;	N-(diphenylmethylene)-1-methyl-1H-benzo[d]imidazol-5-amine (0.446 g, 1.43 mmol)EtOAc dissolved in hydrogen chlorideIn solution (8 mL, 32 mmol, 4 M),The reaction mixture was stirred at room temperature for 7 hours.After the reaction,Wash with water (30mL × 2),The combined aqueous phases were adjusted to pH = 12 with sodium hydroxide powder.The resulting mixture was extracted with a mixed solvent of DCM and MeOH (10/1 (v/v), 100 mL×4).The combined organic layers were dried with anhydrous sodiumThe resulting residue is passed through siliconPurification by column chromatography (DCM/(NH3 in MeOH (7M)) (v/v) = 60/1)The title compound was obtained as a yellow solid (100 mg, yield 47.4%).

Reference： [1]Patent: WO2019/99311,2019,A1 .Location in patent: Paragraph 000548
[2]Patent: CN109776522,2019,A .Location in patent: Paragraph 1368; 1373; 1374; 1375; 1376

49
[ 10394-38-4 ]
6-(4-((2,5-dichloropyrimidin-4-yl)amino)piperidin-1-yl)pyridazine-3-carbonitrile [ No CAS ]
6-(4-((5-chloro-2-((1-methyl-1H-benzo[d]imidazol-5-yl)amino)pyrimidin-4-yl)amino)piperidin-1-yl)pyridazine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100℃;	To a suspension of 6-(4-((2,5-dichloropyrimidin-4-yl)amino)piperidin-l- yl)pyridazine-3-carbonitrile (285.8 mg, 0.82 mmol) and l-methyl-li7-benzo[<i]imidazol-5-amine (149.1 mg, 1.01 mmol) in l,4-dioxane (20 mL) were added Pd(OAc)2 (38.3 mg, 0.17 mmol), BINAP (98%, 106.0 mg, 0.17 mmol) and Cs2C03 (98%, 554.2 mg, 1.67 mmol). The reaction mixture was stirred at 100 C overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/40) to give the title compound as a beige solid (233.3 mg, yield 62%).MS (ESI, pos. ion) m/z: 461.1 [M+H]+;HRMS (ESI, pos. ion) m/z: 461.1740 [M+H]+, calculated value for C22H22ClNio [M+H]+ is 461.1717;1H NMR (400 MHz, DMSO-^) d (ppm): 9.22 (s, 1H), 8.24 (s, 1H), 8.07 (s, 1H), 7.96 (s, 1H), 7.88 (d, J= 9.7 Hz, 1H), 7.50 (dd, J= 8.7, 1.6 Hz, 1H), 7.44 (dd, J= 9.2, 4.4 Hz, 2H), 6.89 (d, J = 7.7 Hz, 1H), 4.66 (d, J= 12.5 Hz, 2H), 4.47 - 4.33 (m, 1H), 3.80 (s, 3H), 3.22 (t, J= 12.3 Hz, 2H), 2.07 (d, J= 10.9 Hz, 2H), 1.67 (qd, J= 12.5, 3.8 Hz, 2H);13C NMR (100 MHz, DMSO-^) d (ppm): 159.1, 158.7, 157.2, 153.9, 145.0, 144.1, 135.9, 131.5, 130.5, 128.8, 117.9, 116.2, 111.6, 109.8, 109.7, 103.3, 48.6, 44.4, 31.1, 31.0.
62%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100℃;	To 6-(4-((2,5-dichloropyrimidin-4-yl)amino)piperidin-1-yl)pyridazine-3-carbonitrile (285.8 mg, 0.82 mmol)And <strong>[10394-38-4]1-methyl-1H-benzo[d]imidazol-5-amine</strong> (149.1 mg, 1.01 mmol)Add in 1,4-dioxane (20mL) solutionPd(OAc) 2 (38.3 mg, 0.17 mmol),BINAP (98%, 106.0 mg, 0.17 mmol)Cs2CO3 (98%, 554.2 mg, 1.67 mmol). The resulting reaction system was stirred at 100 C overnight.After the reaction is completed, concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/40).The title compound was obtained as a beige solid (233.3mg, yield 62%).

Reference： [1]Patent: WO2019/99311,2019,A1 .Location in patent: Paragraph 000560
[2]Patent: CN109776522,2019,A .Location in patent: Paragraph 1431; 1432; 1433; 1434; 1435; 1436; 1437

50
[ 10394-38-4 ]
6-(4-((2,5-dichloropyrimidine-4-yl)amino)piperidin-1-yl)-3-cyanopyridine [ No CAS ]
6-(4-((5-chloro-2-((1-methyl-1H-benzo[d]imidazol-5-yl)amino)pyrimidin-4-yl)amino)piperidin-1-yl)nicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22.7%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere;	A mixture of l-methyl-l//-benzo[<i]imidazol-5-amine (100 mg, 0.67944 mmol), 6- (4-((2,5-dichloropyrimidin-4-yl)amino)piperidin-l-yl)nicotinonitrile (182 mg, 0.5212 mmol), Cs2C03 (508.7 mg, 1.561 mmol), BINAP (34.6 mg, 0.0556 mmol) and Pd(OAc)2 (12.8 mg, 0.0570 mmol) was dissolved with l,4-dioxane (10 mL). The reaction solution was heated to 100 C and stirred for 4 hours under N2 atmosphere and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v) = 50/1) to give the title compound as a white solid (54.4 mg, yield 22.7%).MS (ESI, pos.ion) m/z: 460.1 [M+H]+;1H NMR (600 MHz, DMSO-^) d (ppm): 9.20 (s, 1H), 8.49 (d, J = 2.0 Hz, 1H), 8.22 (s, 1H), 8.06 (s, 1H), 7.94 (s, 1H), 7.84 (dd, j= 9.1, 2.3 Hz, 1H), 7.48 (dd, 7= 8.7, 1.5 Hz, 1H), 7.42 (d, J = 8.7 Hz, 1H), 6.99 (d, J= 9.1 Hz, 1H), 6.88 (d, J= 7.8 Hz, 1H), 4.54 (d, J= 12.1 Hz, 2H), 4.37- 4.29 (m, 1H), 3.79 (s, 3H), 3.10 (t, J= 12.5 Hz, 2H), 2.00 (d, J= 10.6 Hz, 2H), 1.60 (qd, J= 12.5, 3.8 Hz, 2H);13C NMR (150 MHz, DMSO-r/g) d (ppm): 159.0, 158.3, 156.9, 153.6, 152.8, 144.7, 143.7, 140.1, 135.6, 130.1, 119.0, 115.9, 109.6, 109.2, 106.6, 102.9, 94.8, 44.0, 30.8, 30.7.
22.7%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere;	<strong>[10394-38-4]1-methyl-1H-benzo[d]imidazol-5-amine</strong> (100 mg, 0.67944 mmol),6-(4-((2,5-Dichloropyrimidin-4-yl)amino)piperidin-1-yl)nicotinonitrile (182 mg, 0.5212 mmol),Cs2CO3 (508.7 mg, 1.561 mmol),BINAP (34.6mg, 0.0556mmol) andPd(OAc) 2 (12.8 mg, 0.0570 mmol)The mixture was dissolved in 1,4-dioxane (10 mL). The reaction mixture is at 100 C,Stir for 4 hours in a nitrogen atmosphere.After the reaction was completed, it was concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (DCM / MeOH (v/v) = 50/1)The title compound was obtained as a white solid (54.4mg, yield: 22.7%).

Reference： [1]Patent: WO2019/99311,2019,A1 .Location in patent: Paragraph 000549
[2]Patent: CN109776522,2019,A .Location in patent: Paragraph 1368; 1377; 1378; 1379; 1380; 1381

51
[ 10394-38-4 ]
[ 1878-49-5 ]
N-(1-methyl-1H-benzimidazol-5-yl)-2-(2-methylphenoxy)acetamide [ No CAS ]

Reference： [1]MedChemComm,2019,vol. 10,p. 1361 - 1369

52
[ 10394-38-4 ]
[ 17669-01-1 ]
(R,E)-6-acetyl-7,9-dihydroxy-8,9b-dimethyl-2-(1-((1-methyl-1H-benzo[d]imidazol-5-yl)amino)ethylidene)dibenzo[b,d]furan-1,3(2H,9bH)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol; at 80℃; for 4h;Inert atmosphere;	General procedure: (+)-Usnic acid (1 equiv.) and primary ammonia compounds (1.1 equiv.) were added in absolute EtOH under nitrogen and the reaction mixture was stirred at 80C for 4h. For the hydrochloride salt materials, they (1.1 equiv) were added to absolute ethanol, and an equivalent amount of pyridine (1.1 equiv) was added dropwise thereto and stirred at 80C under nitrogen. After 5min, (+) - usnic acid was added and the reaction mixture was stirred for another 4h. After reaction was complete, the reaction solution was cooled and concentrated under reduced pressure. The residues were quickly purified by silica gel column (PE/EtOAc).

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 187

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