[ CAS No. 6775-40-2 ] {[proInfo.proName]}

Name: 6775-40-2|5-Phenyl-1H-imidazol-2-amine|98%
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SKU: A298427
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Quality Control of [ 6775-40-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 6775-40-2 ]

CAS No. :	6775-40-2	MDL No. :	MFCD07382487
Formula :	C₉H₉N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NODFMZCEEBQXME-UHFFFAOYSA-N
M.W :	159.19	Pubchem ID :	12733693
Synonyms :

Calculated chemistry of [ 6775-40-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	48.43
TPSA :	54.7 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) :	-6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.94
Log Po/w (XLOGP3) :	1.38
Log Po/w (WLOGP) :	1.67
Log Po/w (MLOGP) :	0.85
Log Po/w (SILICOS-IT) :	1.86
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.31
Solubility :	0.782 mg/ml ; 0.00491 mol/l
Class :	Soluble
Log S (Ali) :	-2.13
Solubility :	1.17 mg/ml ; 0.00738 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.38
Solubility :	0.0662 mg/ml ; 0.000416 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.83

Safety of [ 6775-40-2 ]

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

Application In Synthesis of [ 6775-40-2 ]

* 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 [ 6775-40-2 ]
Downstream synthetic route of [ 6775-40-2 ]

[ 6775-40-2 ] Synthesis Path-Upstream 1~5

1
[ 160041-64-5 ]
[ 6775-40-2 ]

Yield	Reaction Conditions	Operation in experiment
33%	With hydrogenchloride In methanol; water for 3 h; Reflux	A mixture of 17 (500 mg), 6 M HCl (2.2 mL), and MeOH (2.5 mL)was refluxed for 3 h. After cooling the mixture to room temperature,the precipitate was filtered off and the filtrate was then concentratedin vacuo. The obtained residue was dissolved in H2O andthe resulting solution was neutralized with 1 M NaOH. The precipitatewas collected in vacuo and then washed with H2O and Et2O togive 18 (131 mg, 33percent) as a pale brown solid. 1H NMR (DMSO-d6) d5.25 (2H, s), 6.96 (1H, s), 7.07 (1H, t, J = 7.5 Hz), 7.26 (2H, t,J = 7.5 Hz), 7.57 (2H, d, J = 7.5 Hz), 10.53 (1H, br s); FAB MS m/e(M+H)+ 160; HRMS (ESI) Calcd for C9H10N3 (M+H)+: 160.0875,found: 160.0871; Anal. Calcd for C9H9N30.3H2O: C, 65.68; H,5.88; N, 25.53. Found: C, 65.81; H, 5.49; N, 25.19.

Reference： [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 2806 - 2822
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3873 - 3881
[3] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 524 - 530
[4] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 6, p. 1410 - 1418

2
[ 15764-47-3 ]
[ 6775-40-2 ]

Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 37, p. 5218 - 5220

3
[ 70-11-1 ]
[ 6775-40-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3873 - 3881
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 2806 - 2822
[3] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 6, p. 1410 - 1418

4
[ 113-00-8 ]
[ 98-86-2 ]
[ 6775-40-2 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 6, p. 526 - 528

5
[ 5699-40-1 ]
[ 70-11-1 ]
[ 6775-40-2 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 524 - 530
[2] Medicinal Chemistry Research, 2017, vol. 26, # 5, p. 1010 - 1021

[ 6775-40-2 ] Synthesis Path-Downstream 1~88

1
[ 113-00-8 ]
[ 98-86-2 ]
[ 6775-40-2 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 526 - 528

2
[ 6775-40-2 ]
[ 76507-31-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 526 - 528

3
[ 15764-47-3 ]
[ 6775-40-2 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 5218 - 5220

4
[ 104990-30-9 ]
[ 6775-40-2 ]
[ 1245236-87-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4395 - 4398

5
2-isoquinolin-3-yl-1H-benzoimidazole-4-carboxylic acid [ No CAS ]
[ 6775-40-2 ]
2-isoquinolin-3-yl-1H-benzoimidazole-4-carboxylic acid (4-phenyl-1H-imidazol-2-yl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.5%		General procedure A: Amide formationTo a solution of carboxylic acid (1.0 mmol) in dry DMF (2.5 niL) was added HBTU(1.2 mmol) in one portion, the reaction mixture was stirred at room temperature for 10 min, and then an amine (1.0 mmol) and DIEA (0.8 mL) were added subsequently. The resulting reaction mixture was stirred at room temperature for 12 h or in some cases at 70 0C for 1-3 h.The reaction mixture was diluted with water (50 mL) and the product was precipitated. The product was either isolated after filtration, subsequent washings with water and ethyl acetate or silica gel column chromatography.; 120 mg (0.4 mmol) of 2-isoquinolin-3-yl-lH-benzoimidazole-4-carboxylic acid was reacted with 400 mg (1.1 mmol) of HBTU and 160 mg (1.0 mmol) of 4-phenyl-lH-imidazol- 2-ylamine (160 mg, 1 mmol) according to the general procedure A. The residue was purified by flash column chromatography (EtOAc) to provide 2-isoquinolin-3-yl-lH-benzoimidazole- 4-carboxylic acid (4-phenyl-lH-imidazol-2-yl)-amide (30 mg, 17.5%). LCMS: 431 (M + I)+.

Reference： [1]Patent: WO2006/99379,2006,A2 .Location in patent: Page/Page column 147; 149

6
[ 102-92-1 ]
[ 6775-40-2 ]
[ 1345732-12-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	In toluene;Reflux;	General procedure: The compound 4-phenyloxazol-2-amine (1)/4-phenylthiazol-2-amine (2)/<strong>[6775-40-2]4-phenyl-1H-imidazol-2-amine</strong> (3) (1 mmol), cinnamoyl chloride (0.18 g, 1.1 mmol) and toluene were heated to reflux for 15-18 h. The reaction mixture was cooled and the product was decolourised by treating it with 50/50 carbon/celite (v/v). The reaction mixture was poured through a pad of silica gel (50 ml) and eluted the product with 10% ethyl acetate/hexane. The crude product was then recrystallized from ethyl acetate/hexane.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5317 - 5326
[2]European Journal of Medicinal Chemistry,2014,vol. 82,p. 347 - 354

7
[ 6775-40-2 ]
[ 1345732-21-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5317 - 5326

8
[ 6775-40-2 ]
[ 1345732-30-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5317 - 5326

9
[ 6775-40-2 ]
[ 1345732-39-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5317 - 5326

10
[ 70-11-1 ]
[ 6775-40-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3873 - 3881
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 2806 - 2822
[3]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 1410 - 1418
[4]Journal of Chemical Research,2018,vol. 42,p. 608 - 610
[5]Patent: CN110396116,2019,A

11
[ 160041-64-5 ]
[ 6775-40-2 ]

Yield	Reaction Conditions	Operation in experiment
96%		Compound 5 (200 g, 0.99 mol) and 6 M HCl (3.3 L, 20 mol) wereadded to a 10 L reactor. The mixture was heated to 80 C for 3 h.After completion, monitored by TLC, the solution was cooled to room temperature and the pH was adjusted to 13 with 12 M NaOH underice-cooling. The mixture was extracted with ethyl acetate (2 L × 3).The combined organic layers were washed with water (2 L × 2) dried(anhydrous Na2SO4), filtered and concentrated in vacuum to give ayellow solid; yield 158 g (96%); m.p. 164-165 C; ESI-MS: m/z 160.0[M + H]+; 1H NMR (600 MHz, DMSO-d6), delta (ppm): 10.41 (br, 1H),7.58 (d, J = 6.9 Hz, 2H), 7.26 (t, J = 7.6 Hz, 2H), 7.08 (t, J = 7.4 Hz, 1H),6.96 (s, 1H), 5.24 (s, 2H).
33%	With hydrogenchloride; In methanol; water; for 3h;Reflux;	A mixture of 17 (500 mg), 6 M HCl (2.2 mL), and MeOH (2.5 mL)was refluxed for 3 h. After cooling the mixture to room temperature,the precipitate was filtered off and the filtrate was then concentratedin vacuo. The obtained residue was dissolved in H2O andthe resulting solution was neutralized with 1 M NaOH. The precipitatewas collected in vacuo and then washed with H2O and Et2O togive 18 (131 mg, 33%) as a pale brown solid. 1H NMR (DMSO-d6) d5.25 (2H, s), 6.96 (1H, s), 7.07 (1H, t, J = 7.5 Hz), 7.26 (2H, t,J = 7.5 Hz), 7.57 (2H, d, J = 7.5 Hz), 10.53 (1H, br s); FAB MS m/e(M+H)+ 160; HRMS (ESI) Calcd for C9H10N3 (M+H)+: 160.0875,found: 160.0871; Anal. Calcd for C9H9N30.3H2O: C, 65.68; H,5.88; N, 25.53. Found: C, 65.81; H, 5.49; N, 25.19.

Reference： [1]Journal of Chemical Research,2018,vol. 42,p. 608 - 610
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 2806 - 2822
[3]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3873 - 3881
[4]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 524 - 530
[5]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 1410 - 1418

12
Z-(2-phenylethenesulfonyl)acetyl chloride [ No CAS ]
[ 6775-40-2 ]
C₁₉H₁₇N₃O₃S [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2013,vol. 61,p. 516 - 523

13
[ 79-04-9 ]
[ 6775-40-2 ]
2-chloro-N-(4-phenyl-1H-imidazol-2-yl)acetamide [ No CAS ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 511 - 520

14
[ 6775-40-2 ]
2-((4-phenyl-1H-imidazol-2-ylcarbamoyl)methylthio)acetic acid [ No CAS ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 511 - 520

15
[ 6775-40-2 ]
2-((4-phenyl-1H-imidazol-2-ylcarbamoyl)methylsulfonyl)acetic acid [ No CAS ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 511 - 520

16
[ 6775-40-2 ]
methyl 2-((4-phenyl-1H-imidazol-2-ylcarbamoyl)methylsulfonyl)acetate [ No CAS ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 511 - 520

17
[ 6775-40-2 ]
2-((4-phenyl-1H-imidazol-2-ylcarbamoyl)methylsulfonyl)acetohydrazide [ No CAS ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 511 - 520

18
[ 6775-40-2 ]
2-(((5-(o-chlorophenyl)-1,3,4-oxadiazol-2-yl)methyl)sulfonyl)-N-(4-phenyl-1H-imidazol-2-yl)acetamide [ No CAS ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 511 - 520

19
[ 7646-91-5 ]
[ 6775-40-2 ]
[ 1590443-72-3 ]

Reference： [1]Archiv der Pharmazie,2014,vol. 347,p. 221 - 228

20
[ 6992-26-3 ]
[ 6775-40-2 ]
[ 1590443-81-4 ]

Reference： [1]Archiv der Pharmazie,2014,vol. 347,p. 221 - 228

21
[ 6775-40-2 ]
[ 1616983-94-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 82,p. 347 - 354

22
[ 6775-40-2 ]
[ 1616984-03-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 82,p. 347 - 354

23
[ 6775-40-2 ]
[ 1616984-12-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 82,p. 347 - 354

24
[ 6775-40-2 ]
2-((4-phenyl-1H-imidazol-2-yl)sulfamoyl)acetic acid [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. 1875 - 1882
[2]Research on Chemical Intermediates,2015,vol. 41,p. 4413 - 4426

25
[ 6775-40-2 ]
C₂₀H₁₈N₆O₃S [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. 1875 - 1882

26
2-((4-phenyl-1H-imidazol-2-yl)sulfamoyl)acetic acid [ No CAS ]
[ 6775-40-2 ]
C₂₀H₁₈N₆O₃S [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. 1875 - 1882

27
[ 55896-93-0 ]
[ 6775-40-2 ]
ethyl 2-((4-phenyl-1H-imidazol-2-yl)sulfamoyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In dichloromethane;	General procedure: To a solution of 4-aryl-1H-imidazol-2-amine (1) (0.477 g, 3.0 mmol) in dichloromethane(10 mL), triethylamine (3.1 mmol), and 4-dimethylaminopyridine (DMAP) (0.1 mmol) were added and stirred at room temperature for 15 min. Then, a solution of ethyl 2-chlorosulfonylacetate (0.615 g, 3.3 mmol) in dichloromethane(5 mL) was added dropwise and the reaction mixture was stirred at 40 C under nitrogen atmosphere for 6-10 h. After completion of reaction the solvent was removed in vacuo. The resultant residue was neutralized with saturated NaHCO3 solution and the aqueous layer was extracted with ethyl acetate, washed with water and dried over anhydrous Na2SO4. The solvent was removed under vacuum and the resultant solid was purified by column chromatography (silica gel, 60-120 mesh) using hexane-ethyl acetate (3:1) as eluent.

Reference： [1]Chemistry and biodiversity,2019,vol. 16
[2]Journal of Heterocyclic Chemistry,2014,vol. 51,p. 1875 - 1882
[3]Research on Chemical Intermediates,2015,vol. 41,p. 4413 - 4426

28
[ 1155273-85-0 ]
[ 6775-40-2 ]
2-(4'-phenylsulfonyl-1'H-pyrrol-3'-ylsulfonyl)-N-(4-phenyl-1H-imidazol-2-yl)acetamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,2014,vol. 23,p. 4500 - 4509
[2]Medicinal Chemistry Research,2014,vol. 23,p. 4500 - 4509

29
[ 1155273-85-0 ]
[ 6775-40-2 ]
E-(2-phenylsulfonylethenesulfonyl)-N-(4-phenyl-1H-imidazol-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: The compound E-arylsulfonylethenesulfonylacetic acid(1) (10 mmol) was dissolved in 3 ml of DMF. To this HATU (20 mmol) was added and stirred at room temperature for 15-20 min. Then, DIPEA (20 mmol) followed by the compound 2/3/4 (10 mmol) were added and continued stirring at ambient temperature for 19-22 h.The reaction mixture was poured onto ice-water, filtered the separated solid and dried. It was recrystallized from 2-propanol.

Reference： [1]Medicinal Chemistry Research,2014,vol. 23,p. 4500 - 4509
[2]Medicinal Chemistry Research,2014,vol. 23,p. 4500 - 4509

30
[ 6775-40-2 ]
N-[(4-phenyl)thiazol-2-yl]-2-(4-phenyl-1H-imidazol-2-ylsulfamoyl)acetamide [ No CAS ]

Reference： [1]Research on Chemical Intermediates,2015,vol. 41,p. 4413 - 4426

31
[ 6775-40-2 ]
N-[4-(4-methylphenyl)thiazol-2-yl]-2-(4-phenyl-1H-imidazol-2-ylsulfamoyl)acetamide [ No CAS ]

Reference： [1]Research on Chemical Intermediates,2015,vol. 41,p. 4413 - 4426

32
[ 6775-40-2 ]
N-[4-(4-chlorophenyl)thiazol-2-yl]-2-(4-phenyl-1H-imidazol-2-ylsulfamoyl)acetamide [ No CAS ]

Reference： [1]Research on Chemical Intermediates,2015,vol. 41,p. 4413 - 4426

33
4,6-diphenylpyrimidin-2-ylsulfamoyl chloride [ No CAS ]
[ 6775-40-2 ]
N-((4-phenyl-1H-imidazol-2-ylamino)sulfonyl)-4,6-diphenylpyrimidin-2-amine [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 524 - 530

34
[ 5699-40-1 ]
[ 70-11-1 ]
[ 6775-40-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 524 - 530
[2]Medicinal Chemistry Research,2017,vol. 26,p. 1010 - 1021

35
[ 26280-19-3 ]
[ 6775-40-2 ]
2-(5-benzoyl-1-methyl-1H-pyrrol-2-yl)-N-(4'-phenyl-1H-imidazol-2'-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		General procedure: The (5-benzoyl-1-methyl-1H-pyrrol-2-yl)acetic acid (6)(1 mmol) was dissolved in dry DMF. To this TBTU (2mmol) was added and stirred for 30 min under nitrogenatmosphere. Then 4-aryloxazol-2-amine (7)/4-arylthiazol-2-amine (8)/4-aryl-1H-imidazol-2-amine (9) (1 mmol) followedby DIPEA (0.5 ml) were added and the reactionmixture was heated at 50 C for 6 h. After completion ofreaction (progress of reaction was monitored by TLC) thecontents were allowed to cool and poured into ice water.The resultant solid was filtered, dried and recrystallizedfrom 2-propanol.

Reference： [1]Medicinal Chemistry Research,2017,vol. 26,p. 1010 - 1021

36
[ 98-88-4 ]
[ 6775-40-2 ]
C₁₆H₁₃N₃O [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 1376 - 1383

37
[ 6775-40-2 ]
N-(5-(chlorosulfonyl)-4-phenyl-1H-imidazol-2-yl)benzamide [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 1376 - 1383

38
[ 6775-40-2 ]
N-(5-(aminosulfonyl)-4-phenyl-1H-imidazol-2-yl)benzamide [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 1376 - 1383
[2]Arkivoc,2019,vol. 2019

39
[ 6775-40-2 ]
bis(2-benzamido-4-phenyl-1H-imidazol-5-ylsulfonyl)amine [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 1376 - 1383
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 1376 - 1383

40
[ 607-68-1 ]
[ 6775-40-2 ]
N2,N4-bis(4-phenyl-1H-imidazol-2-yl)quinazoline-2,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With hydrogenchloride; In isopropyl alcohol; at 20℃;Sonication;	General procedure: A solution of 2,4-dichloroquinazoline (1, 1.0 mmol),4-aryloxazol-2-amine 2/4-arylthiazol-2-amine 3/4-aryl-1H-imidazol-2-amine 4 (2.5 mmol) and conc. HCl(2.0 mmol) in 5 cm3 2-propanol was sonicated at roomtemperature for 30-45 min in an ultrasonic bath working at 46 kHz (constant frequency). After completion of there action (monitored by TLC), the separated solid was filtered, dried, and recrystallized from 2-propanol.

Reference： [1]Monatshefte fur Chemie,2017,vol. 148,p. 1781 - 1792

41
2-(N-(4,6-diphenylpyrimidin-2-yl)sulfamoyl)acetic acid [ No CAS ]
[ 6775-40-2 ]
2-(N-(4,6-diphenylpyrimidin-2-yl)sulfamoyl)-N-(4-phenyl-1H-imidazol-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 25℃;Inert atmosphere;	General procedure: A solution of EDCI (10 mmol) and HOBt (10 mmol) inDMF (8 mL) was added dropwise to a stirred suspension ofacid 4 (9.09 mmol) and 5/6/7 (10 mmol) in DMF (15 mL) at0 C under nitrogen atmosphere. DIPEA (20 mmol) wasadded dropwise to the mixture and continued stirring at 25 C for 12-16 h. EtOAc (80 mL) was added and the organiclayer was washed with brine (4 × 20 mL), dried (Na2SO4),and concentrated in vacuo. Purification of the residue bycolumn chromatography (silica gel, PE-EtOAc, 3:2) affordedthe compounds 8/9/10.

Reference： [1]Medicinal Chemistry Research,2017,vol. 26,p. 2568 - 2582

42
[ 4637-24-5 ]
[ 6775-40-2 ]
C₁₂H₁₄N₄ [ No CAS ]

Reference： [1]RSC Advances,2017,vol. 7,p. 51062 - 51068

43
[ 420-04-2 ]
[ 122-51-0 ]
[ 6775-40-2 ]
4-amino-7-phenylimidazo[1,2-a][1,3,5]triazine [ No CAS ]

Reference： [1]RSC Advances,2017,vol. 7,p. 51062 - 51068

44
C₁₃H₁₃ClN₂O₂ [ No CAS ]
[ 6775-40-2 ]
2-(4-(1-methyl-1H-imidazol-4-yl)phenoxy)-N-(4-phenyl-1H-imidazol-2-yl)propanamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 2806 - 2822

45
[ 420-04-2 ]
[ 78-39-7 ]
[ 6775-40-2 ]
4-amino-2-methyl-7-phenylimidazo[1,2-a][1,3,5]triazine [ No CAS ]

Reference： [1]RSC Advances,2018,vol. 8,p. 21495 - 21504

46
[ 420-04-2 ]
[ 6775-40-2 ]
[ 115-80-0 ]
4-amino-2-ethyl-7-phenylimidazo[1,2-a][1,3,5]triazine [ No CAS ]

Reference： [1]RSC Advances,2018,vol. 8,p. 21495 - 21504

47
[ 420-04-2 ]
[ 24964-76-9 ]
[ 6775-40-2 ]
4-amino-2-propyl-7-phenylimidazo[1,2-a][1,3,5]triazine [ No CAS ]

Reference： [1]RSC Advances,2018,vol. 8,p. 21495 - 21504

48
[ 420-04-2 ]
[ 919-29-9 ]
[ 6775-40-2 ]
4-amino-2-butyl-7-phenylimidazo[1,2-a][1,3,5]triazine [ No CAS ]

Reference： [1]RSC Advances,2018,vol. 8,p. 21495 - 21504

49
[ 110-91-8 ]
[ 6775-40-2 ]
C₁₅H₁₈N₄O [ No CAS ]

Reference： [1]RSC Advances,2018,vol. 8,p. 21495 - 21504

50
[ 42518-98-9 ]
[ 6775-40-2 ]
5-chloro-N-(4-phenyl-1H-imidazol-2-yl)thiophene-2-carboxamide [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 1410 - 1418

51
[ 6775-40-2 ]
[ 74-88-4 ]
[ 6653-45-8 ]

Yield	Reaction Conditions	Operation in experiment
47.5%		Compound 6 (100 g, 0.63 mol) and DMF (1 L) were added to a 2 Lthree-necked flask. The mixture was cooled to -10 C, and sodiumhydride (37.8 g, 0.96 mol, 60% dispersion in mineral oil) was added inportions to maintain the temperature below 0 C. After the addition,the mixture was stirred for 30 min. Then a solution of iodomethane(50 mL, 0.79 mol) in DMF (50 mL) was added dropwise below -10 Cand the mixture was stirred at -10 C for another 4 h. After completionof the reaction, monitored by TLC, 10% sodium hydroxide (100 mL)was added and stirred for 30 min at room temperature. The reactionsolution was poured into water (1.5 L) and extracted with ethyl acetate(2 L × 3). The combined organic layers were washed with water(1 L × 3), brine (1 L) and dried over anhydrous Na2SO4, filtered andconcentrated in vacuum to give the crude product (120 g). The crudeproduct was recrystallised from ethanol (200 mL) to provide a pinksolid; yield 51.8 g (47.5%); m.p. 218-220 C; ESI-MS: m/z 174.0 [M+ H]+; 1H NMR (600 MHz, DMSO-d6), delta (ppm): 7.59-7.57 (dd, J =1.3 Hz, 8.3 Hz, 2H), 7.26 (t, J = 7.7 Hz, 2H), 7.09-7.07 (m, 1H), 7.03(s, 1H), 5.49 (s, 1H), 3.35 (s, 3H); 13C NMR (150 MHz, DMSO-d6), delta:150.39, 135.89, 135.47, 128.69, 125.57, 123.91, 112.36, 31.63.

Reference： [1]Journal of Chemical Research,2018,vol. 42,p. 608 - 610

52
[ 2033-24-1 ]
[ 100-52-7 ]
[ 6775-40-2 ]
5-((2-amino-4-phenyl-1H-imidazol-5-yl)(phenyl)methyl)-6-hydroxy-2,2-dimethyl-4H-1,3-dioxin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	In isopropyl alcohol;Reflux;	General procedure: An equimolar mixture (1.0 mmol) of thecorresponding 2-amino-4-arylimidazole 1, aromatic aldehyde 2and Meldrum?s acid 3 was refluxed in iPrOH (3 mL) for3-5 min. After cooling, the solid products 4 were filtered off,washed with iPrOH and dried on air. 4a: colourless solid, 77%;mp 243-245 C; IR (KBr, cm-1) nu: 3404-2800 (NH2, NH, OH),1684 (C=O); 1H NMR (200 MHz, DMSO-d6) delta 12.27 (br s, 2H,NH, OH), 7.61-7.49 (m, 2H, Harom), 7.48-7.31 (m, 5H, Harom),7.27-7.01 (m, 5H, NH2,, Harom), 5.48 (s, 1H, CH), 1.51 (s, 6H,CH3); 13C NMR (125 MHz, CDCl3) delta 166.8 (C=O), 146.6(C-OH), 144.0, 129.4, 128.9, 128.4, 128.3, 127.5, 127.4, 127.2,125.9, 121.1, 100.6, 76.0 (C=COH), 35.1 (CH), 26.4 (CH3),25.9 (CH3); MS (m/z) (%): 289 (76), (391 [M+?] - 44 -58), 247(53), 159 (36), 104 (19), 77 (8), 44 (39), 43 (100); anal. calcdfor C22H21N3O4 (391.5) C, 67.52; H, 5.37; N, 10.74; found: C,68.77; H, 5.93; N, 10.79.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

53
[ 2033-24-1 ]
[ 104-87-0 ]
[ 6775-40-2 ]
5-((2-amino-4-phenyl-1H-imidazol-5-yl)(p-tolyl)methyl)-6-hydroxy-2,2-dimethyl-4H-1,3-dioxin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	In isopropyl alcohol;Reflux;	General procedure: An equimolar mixture (1.0 mmol) of thecorresponding 2-amino-4-arylimidazole 1, aromatic aldehyde 2and Meldrum?s acid 3 was refluxed in iPrOH (3 mL) for3-5 min. After cooling, the solid products 4 were filtered off,washed with iPrOH and dried on air.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

54
[ 100-52-7 ]
[ 6775-40-2 ]
3-amino-1,7-diphenyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-one [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

55
[ 100-52-7 ]
[ 105-56-6 ]
[ 6775-40-2 ]
ethyl 5-amino-3-(benzylideneamino)-1,7-diphenyl-7H-pyrrolo[1,2-c]imidazole-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	In isopropyl alcohol;Reflux;	General procedure: A mixture of the corresponding 2-amino-4-arylimidazole 1(1.0 mmol), aromatic aldehyde 2 (2.0 mmol) and ethyl 2-cyanoacetate 15 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products 16were filtered off and crystallized from iPrOH. 16a: yellowpowder, 30%, mp 239-240 C; 1H NMR (200 MHz, DMSO-d6)delta 9.32 (s, 1H, CHazomethine), 8.12 (d, J = 6.7 Hz, 2, Ar),7.67-7.45 (m, 5, Ar), 7.27-7.04 (m, 10, C5NH2, Ar), 5.15(s, J = 6.7 Hz, 1H, C7H), 4.05-3.84 (m, 2, 23), 1.01(s, J = 7.0, 3H, 2CH3); 13C NMR (125 MHz, DMSO-d6) delta178.7 (CO), 134.5, 133.3, 130.2, 129.6, 128.7, 128.6, 128.3, 127.8, 127.2, 127.0, 126.4, 125.8, 125.5, 116.7, 93.4, 58.9, 43.4,14.7; MS (m/z) (%): 448 ([M+?], 100; anal. calcd. forC28H24N4O2 (448.19) C, 74.98; H, 5.39; N, 12.49; found: ,75.12; H, 4.89; N, 11.37.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

56
[ 104-87-0 ]
[ 6775-40-2 ]
[ 109-77-3 ]
5-amino-3-(4-methylbenzylideneamino)-1-phenyl-7-p-tolyl-7H-pyrrolo[1,2-c]imidazole-6-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	In isopropyl alcohol;Reflux;	General procedure: A mixture of the corresponding 2-amino-4-arylimidazole1 (1.0 mmol), aromatic aldehyde 2 (2.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products14 were filtered off and crystallized from iPrOH. 14a:yellow powder, 65%; mp 221-222 C; 1H NMR (200 MHz,DMSO-d6) delta 9.34 (s, 1H, CHazomethine), 8.18 (d, J = 7.3 Hz,2H, Ar), 7.68-7.48 (m, 7H, Ar, C5NH2 ), 7.31-7.10 (m, 8H,Ar), 5.34 (s, 1H, C7H); 13C NMR (125 MHz, DMSO-d6) delta162.4 (3), 149.5 (Cazomethine), 143.8 (C5), 138.3, 135.3, 133.3,133.0, 132.5, 132.1, 130.4, 129.5, 129.4, 128.8, 128.2, 128.1,127.4, 125.8, 117.9 (N), 71.7 (C6), 45.01 (C7); MS (m/z) (%):429 ([M+?], 25), 285 (100), 194 (19), 104 (26), 77 (19), 43 (25);anal. calcd for C28H23N5 (429.53) C, 78.30; H, 5.40; N, 16.31;found: C, 80.25; H, 5.70; N, 13.41.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

57
[ 6775-40-2 ]
3-(2-amino-4-phenyl-1H-imidazol-5-yl)-3-(p-tolyl)propanoic acid [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045
[2]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

58
[ 6775-40-2 ]
5-oxo-1-phenyl-7-(p-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-3-aminium 2,2,2-trifluoroacetate [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

59
[ 1122-91-4 ]
[ 6775-40-2 ]
[ 109-77-3 ]
5-amino-3-((4-bromobenzylidene)amino)-7-(4-bromophenyl)-1-phenyl-7H-pyrrolo[1,2-c]imidazole-6-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In isopropyl alcohol;Reflux;	General procedure: A mixture of the corresponding 2-amino-4-arylimidazole1 (1.0 mmol), aromatic aldehyde 2 (2.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products14 were filtered off and crystallized from iPrOH.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

60
[ 459-57-4 ]
[ 6775-40-2 ]
[ 109-77-3 ]
5-amino-3-((4-fluorobenzylidene)amino)-7-(4-fluorophenyl)-1-phenyl-7H-pyrrolo[1,2-c]imidazole-6-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	In isopropyl alcohol;Reflux;	General procedure: A mixture of the corresponding 2-amino-4-arylimidazole1 (1.0 mmol), aromatic aldehyde 2 (2.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products14 were filtered off and crystallized from iPrOH.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

61
[ 2058-74-4 ]
[ 6775-40-2 ]
[ 109-77-3 ]
3',5'-diamino-1-methyl-2-oxo-1'-phenylspiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In isopropyl alcohol;Reflux;	General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxed during 50-60 min. After cooling, the solid products 19 were filtered off and crystallized from iPrOH. 19a: colourless solid, 60%, mp 250-252 C, 1H NMR (200 MHz, DMSO-d6) delta7.77 (br s, 2H, 5?NH2), 7.37 (t, J = 7.9 Hz, 1H, Arisatin),7.24-7.10 (m, 2H, Ar), 7.10-6.95 (m, 4H, Ar), 6.94-6.82 (m,2H, Ar), 6.47 (br s, 2H, 3?NH2imidazole), 3.21 (s, 3H, N1CH3);13C NMR (125 MHz, DMSO-d6) delta 176.3 (C2), 154.2 (C5?),146.4 (3?), 145.7, 135.4, 133.0, 132.2, 130.7, 130.3, 129.0,127.2, 126.6, 126.1, 126.0, 111.7, 69.8 (C6?), 55.8 (spiro), 29.2(N13); MS (m/z) (%): 369 [M + H]+ (100); anal. calcd forC21H16N6O (368.14) C, 68.47; H, 4.38; N, 22.81; found: ,69.43; H, 5.07; N, 22.64.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

62
[ 2058-72-2 ]
[ 6775-40-2 ]
[ 109-77-3 ]
3',5'-diamino-5-bromo-1-methyl-2-oxo-1'-phenylspiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In isopropyl alcohol;Reflux;	General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxed during 50-60 min. After cooling, the solid products 19 were filtered off and crystallized from iPrOH.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

63
[ 66440-60-6 ]
[ 6775-40-2 ]
[ 109-77-3 ]
3',5'-diamino-1,5-dimethyl-2-oxo-1'-phenylspiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In isopropyl alcohol;Reflux;	General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxed during 50-60 min. After cooling, the solid products 19 were filtered off and crystallized from iPrOH.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

64
[ 913547-30-5 ]
[ 6775-40-2 ]
[ 109-77-3 ]
3',5'-diamino-1-(4-chlorobenzyl)-5-fluoro-2-oxo-1'-phenylspiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In isopropyl alcohol;Reflux;	General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxed during 50-60 min. After cooling, the solid products 19 were filtered off and crystallized from iPrOH.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

65
[ 1122-91-4 ]
[ 105-56-6 ]
[ 6775-40-2 ]
ethyl 5-amino-3-((4-bromobenzylidene)amino)-7-(4-bromophenyl)-1-phenyl-7H-pyrrolo[1,2-c]imidazole-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In isopropyl alcohol;Reflux;	General procedure: A mixture of the corresponding 2-amino-4-arylimidazole 1(1.0 mmol), aromatic aldehyde 2 (2.0 mmol) and ethyl 2-cyanoacetate 15 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products 16were filtered off and crystallized from iPrOH.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

66
[ 2058-74-4 ]
[ 105-56-6 ]
[ 6775-40-2 ]
ethyl 3',5'-diamino-1-methyl-2-oxo-1'-phenylspiro[indoline-3,7'-pyrrolo[1,2-c]imidazole]-6'-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In isopropyl alcohol;Reflux;	General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) and ethyl 2-cyanoacetate 15 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 50-60 min. After cooling, the solid products 20were filtered off and crystallized from iPrOH. 20a: colourlesssolid, 72%, mp 280-282 C; 1H NMR (200 MHz, DMSO-d6) delta7.63 (br s, 2H, 5?NH2), 7.29 (t, J = 7.5 Hz, 1H, Ar), 7.11-6.88(m, 8, Ar), 6.46 (br s, 2H, 3?NH2), 3.83-3.63 (m, 2,23), 3.21 (s, 3, N13), 0.88-0.69 (m, 3,23); 13C NMR (125 MHz, DMSO-d6) delta 175.0 (C2),145.0 (C5?), 143.7 (3?), 133.6, 130.4, 130.2, 129.0, 128.5,126.7, 125.3, 125.0, 123.5, 123.1, 108.6, 58.5 (C6?), 52.7(spiro), 33.4 (23), 26.9 (N13), 14.3 (23);MS (m/z) (%): 416 [M + H]+ (100); anal. calcd for C23H21N5O3(415.16) C, 66.49; H, 5.09; N, 16.86; found: , 67.89; H, 5.64;N, 11.70.

Reference： [1]Beilstein Journal of Organic Chemistry,2019,vol. 15,p. 1032 - 1045

67
[ 6775-40-2 ]
N-((2-benzamido-4-phenyl-1H-imidazol-5-yl)sulfonyl)furan-2-carboxamide [ No CAS ]