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[ CAS No. 22265-37-8 ] {[proInfo.proName]}

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Chemical Structure| 22265-37-8
Chemical Structure| 22265-37-8
Structure of 22265-37-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 22265-37-8 ]

CAS No. :22265-37-8 MDL No. :MFCD00029547
Formula : C8H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :CSISQILZUHMAJB-UHFFFAOYSA-N
M.W : 150.18 Pubchem ID :229074
Synonyms :
4-Methoxybenzimidamide

Calculated chemistry of [ 22265-37-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 44.2
TPSA : 59.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.21
Log Po/w (XLOGP3) : 1.12
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 1.1
Consensus Log Po/w : 1.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.75
Solubility : 2.68 mg/ml ; 0.0179 mol/l
Class : Very soluble
Log S (Ali) : -1.95
Solubility : 1.67 mg/ml ; 0.0111 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.24
Solubility : 0.864 mg/ml ; 0.00575 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.06

Safety of [ 22265-37-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3263
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 22265-37-8 ]

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

  • Downstream synthetic route of [ 22265-37-8 ]

[ 22265-37-8 ] Synthesis Path-Downstream   1~75

  • 1
  • [ 3717-22-4 ]
  • [ 22265-37-8 ]
YieldReaction ConditionsOperation in experiment
With ammonia; potassium amide
  • 2
  • [ 36568-05-5 ]
  • [ 22265-37-8 ]
  • [ 92846-98-5 ]
YieldReaction ConditionsOperation in experiment
With 5-ethyl-2-methyl-pyridine
  • 3
  • [ 10531-41-6 ]
  • [ 22265-37-8 ]
  • [ 70552-21-5 ]
YieldReaction ConditionsOperation in experiment
In chloroform at 25℃;
  • 4
  • [ 874-90-8 ]
  • [ 22265-37-8 ]
YieldReaction ConditionsOperation in experiment
96% With amino(methyl)aluminum chloride In toluene at 80℃;
85% With trimethylaluminum; ammonium chloride In toluene at 80℃; for 16h;
85% With trimethylaluminum; ammonium chloride In toluene at 0 - 80℃; for 16.7h; 1.1 To a suspension of NH4CI (5.0 g, 93.5 mmol) in toluene (100 mL) with stirring was added AI(CH3)3 in toluene (47 mL, 2.0 M) at 0 °C over 10 min. The mixture was allowed to reach room temperature, stirred for 30 min, and a solution of 4-methoxybenzonitrile (12.6 g, 93.5 mmol) in toluene (20 mL) was injected. The mixture was heated at 80 °C for 16 hours, then cooled to room temperature, and poured into a slurry of silica gel (200 g) in CHCI3 (500 mL). The mixture was stirred for 5 min and the silica gel was filtered. The filter cake was further washed with methanol (300 mL). Evaporation of the filtrate gave product (12.0 g, 85%) as a white solid.
81% With trimethylaluminum; ammonium chloride In toluene at 80℃; for 18h; Inert atmosphere; IV Scheme IV To a suspension of NH4CI (631 mg, 11.799mmol) in anhydrous toluene (12mL) at 0°C under nitrogen was slowly added AI(CH3)3solution (5.9mL, 2.0 in toluene) over 5 minutes. Suspension stirred at 0°C for 5 minutes and then slowly warmed to room temperature, stirring an additional 30 minutes at room temp. To this stirring solution was then added 4-methoxybenzonitrile (1.57g, 11.79mmol) in 2.5mL of toluene. The reaction was heated to 80°C. After 18 hours, the reaction solution was cooled to room temperature and was carefully poured into a slurry of Si02 (25g) in CHCI3 (60mL). After stirring for 10 minutes, the mixture was filtered and the filter cake was rinsed with MeOH (50mL). The filtrate was concentrated to give 1.43g (81%) of benzimidamide as a white solid, which was used without further purification. A suspension of benzimidamide (459mg, 3.056mmol), carbondisulfide (460mL, 7.62mmol) and sulfur (121mg, 3.774mmol) in MeOH (3.8ml_) was stirred under nitrogen at room temperature. To this was slowly added 1.9mL of sodium methoxide solution (25% w/v in MeOH). Upon complete addition, solution was heated to reflux. After 24 hours, the reaction solution was cooled to room temperature and the pH of the solution was adjusted to 4 with aqueous HCI (1 M). The yellow precipitate that formed was filtered and dried to afford 249mg (36%) of 3-(4-methoxyphenyl)-1,2,4-thiadiazole-5-thiol, which was used without further purification.
22.2% Stage #1: 4-methoxybenzonitrile With lithium bis(trimethylsilyl)amide diethyl etherate In diethyl ether for 20h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; ethanol; water Stage #3: With sodium hydroxide In water
With ammonia; ammonium bromide
With lithium hexamethyldisilazane In diethyl ether for 2h; Ambient temperature;
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 48 h / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / water / 1 h / 20 °C
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium hydrogencarbonate / methanol / 5 h / Reflux 2: nickel; acetic acid; hydrogen / methanol / 12 h / 20 °C
Stage #1: 4-methoxybenzonitrile With ethanol; acetyl chloride In ethyl acetate at 20℃; for 24h; Stage #2: With sodium; ammonium chloride In methanol; ethyl acetate at 20℃;

Reference: [1]Garigipati [Tetrahedron Letters, 1990, vol. 31, # 14, p. 1969 - 1972]
[2]Sehon, Clark A.; Wang, Gren Z.; Viet, Andrew Q.; Goodman, Krista B.; Dowdell, Sarah E.; Elkins, Patricia A.; Semus, Simon F.; Evans, Christopher; Jolivette, Larry J.; Kirkpatrick, Robert B.; Dul, Edward; Khandekar, Sanjay S.; Yi, Tracey; Wright, Lois L.; Smith, Gary K.; Behm, David J.; Bentley, Ross; Doe, Christopher P.; Hu, Erding; Lee, Dennis [Journal of Medicinal Chemistry, 2008, vol. 51, # 21, p. 6631 - 6634]
[3]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2006/9889, 2006, A1 Location in patent: Page/Page column 30
[4]Current Patent Assignee: UNIVERSITY OF MINNESOTA SYSTEM - WO2013/74059, 2013, A2 Location in patent: Page/Page column 71
[5]Location in patent: experimental part Boere, Rene T.; Roemmele, Tracey L.; Yu, Xin [Inorganic Chemistry, 2011, vol. 50, # 11, p. 5123 - 5136]
[6]Schaefer,F.C.; Krapcho,A.P. [Journal of Organic Chemistry, 1962, vol. 27, p. 1255 - 1258]
[7]Thurkauf, Andrew; Hutchison, Alan; Peterson, John; Cornfield, Linda; Meade, Robin; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 12, p. 2251 - 2255]
[8]Lu, Xiaodong; Xin, Xiaoyi; Wan, Boshun [Tetrahedron Letters, 2018, vol. 59, # 4, p. 361 - 364]
[9]Current Patent Assignee: NANKAI UNIVERSITY - CN109422734, 2019, A
[10]Liu, Kai-Li; Li, Xin-Yang; Wang, De-Pu; Xue, Wen-Han; Qian, Xin-Hua; Li, Yu-Heng; Lin, Qi-Qi; Li, Shuai; Meng, Fan-Hao [Journal of Medicinal Chemistry, 2021, vol. 64, # 18, p. 13356 - 13372]
  • 5
  • [ 684-16-2 ]
  • [ 22265-37-8 ]
  • [ 74177-56-3 ]
YieldReaction ConditionsOperation in experiment
73% With pyridine; trichlorophosphate In diethyl ether at -15℃; for 72h;
  • 6
  • [ 38064-02-7 ]
  • [ 22265-37-8 ]
  • [ 95674-88-7 ]
YieldReaction ConditionsOperation in experiment
46% With triethylamine In diethyl ether at 0 - 5℃; for 2h;
  • 7
  • [ 38064-02-7 ]
  • [ 22265-37-8 ]
  • [ 95675-03-9 ]
YieldReaction ConditionsOperation in experiment
53% With triethylamine In diethyl ether at 0 - 5℃; for 2h;
  • 8
  • [ 22265-37-8 ]
  • [ 933-01-7 ]
  • [ 95675-02-8 ]
YieldReaction ConditionsOperation in experiment
46% With triethylamine In diethyl ether at 0 - 5℃; for 2h;
  • 9
  • [ 22265-37-8 ]
  • [ 118377-76-7 ]
YieldReaction ConditionsOperation in experiment
With trithiazyl trichloride In acetonitrile for 16h; Heating; Yield given;
  • 10
  • [ 22265-37-8 ]
  • [ 76843-77-1 ]
YieldReaction ConditionsOperation in experiment
3.8% With sulfur dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 24h; Ambient temperature;
  • 11
  • [ 62147-49-3 ]
  • [ 22265-37-8 ]
  • [ 53292-67-4 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide; ammonium chloride at 80℃; for 0.5h;
  • 12
  • [ 1867-38-5 ]
  • [ 22265-37-8 ]
  • 4-amino-2-(p-anisyl)-6-(p-chlorophenyl)-pyrimidine-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% In methanol for 7h; Heating;
With piperidine In methanol for 6h; Reflux; Preparation of 4-amino-2,6-diaryl-5-cyanopyrimidines, 3a-s General procedure: An appropriate bisnitrile 2a-s and arylamidine 1a-s (Meloet al. 2002; Do Monte et al. 2016; Melo et al. 2017) inequimolar quantity (3.46 mmol) were dissolved in methanol(10 mL) and refluxed for 6h. The contents were cooled toroom temperature and solvent evaporated to give a solidmass which was crystallized and recrystallized from anappropriate solvent.
  • 13
  • [ 2972-76-1 ]
  • [ 22265-37-8 ]
  • [ 475995-39-2 ]
YieldReaction ConditionsOperation in experiment
31% In methanol for 7h; Heating;
Stage #1: 2-(2,4-dichlorobenzylidene)malononitrile; 4-methoxybenzamidine With potassium carbonate In methanol at 50℃; for 3h; Stage #2: With potassium permanganate In acetone at 20℃; for 3h;
  • 14
  • [ 22265-37-8 ]
  • (E)-2-benzyloxy-3-hydroxybut-2-enedioic acid 4-tert-butyl ester 1-methyl ester [ No CAS ]
  • 5-benzyloxy-2-(4-methoxy-phenyl)-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With sodium methylate In methanol at 20℃; for 30h;
  • 15
  • [ 2826-26-8 ]
  • [ 22265-37-8 ]
  • 4-amino-2,6-bis-(4-methoxy-phenyl)-pyrimidine-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In methanol for 7h; Heating;
With piperidine In methanol for 6h; Reflux; Preparation of 4-amino-2,6-diaryl-5-cyanopyrimidines, 3a-s General procedure: An appropriate bisnitrile 2a-s and arylamidine 1a-s (Meloet al. 2002; Do Monte et al. 2016; Melo et al. 2017) inequimolar quantity (3.46 mmol) were dissolved in methanol(10 mL) and refluxed for 6h. The contents were cooled toroom temperature and solvent evaporated to give a solidmass which was crystallized and recrystallized from anappropriate solvent.
  • 16
  • [ 2700-23-4 ]
  • [ 22265-37-8 ]
  • [ 886761-27-9 ]
YieldReaction ConditionsOperation in experiment
91% With piperidine In methanol for 6h; Reflux; Preparation of 4-amino-2,6-diaryl-5-cyanopyrimidines, 3a-k General procedure: An appropriate bisnitrile 2a-k[8,11] and arylamidine 1a-k[6,10] in equimolar quantity (3.46 mmol) were dissolved in methanol (10 mL) and refluxed for 6h, in the presence piperidine as base. The contentes were cooled to room temperture and solvente evaporated to give a solid mass which was crystallized and recrystalllized from an appropriate solvent.
32% In methanol for 7h; Heating;
With piperidine In methanol for 6h; Reflux; Preparation of 4-amino-2,6-diaryl-5-cyanopyrimidines, 3a-s General procedure: An appropriate bisnitrile 2a-s and arylamidine 1a-s (Meloet al. 2002; Do Monte et al. 2016; Melo et al. 2017) inequimolar quantity (3.46 mmol) were dissolved in methanol(10 mL) and refluxed for 6h. The contents were cooled toroom temperature and solvent evaporated to give a solidmass which was crystallized and recrystallized from anappropriate solvent.
  • 17
  • [ 950203-40-4 ]
  • [ 22265-37-8 ]
  • C27H38N6O8 [ No CAS ]
  • C27H38N6O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 38% 2: 31% Stage #1: methyl 3-tert-butoxycarbonylazo-2-butenoate; 4-methoxybenzamidine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Stage #2: In tetrahydrofuran Heating; Further stages.;
  • 18
  • [ 146000-72-8 ]
  • [ 22265-37-8 ]
  • C21H26N6O8 [ No CAS ]
  • C21H26N6O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 31% 2: 22% Stage #1: (2-methoxycarbonyl-1-methyl-vinyl)-diazenecarboxylic acid methyl ester; 4-methoxybenzamidine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Stage #2: In tetrahydrofuran Heating; Further stages.;
  • 19
  • C13H14N2O4 [ No CAS ]
  • [ 22265-37-8 ]
  • C33H34N6O8 [ No CAS ]
  • C33H34N6O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 32% 2: 20% Stage #1: C13H14N2O4; 4-methoxybenzamidine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Stage #2: In tetrahydrofuran Heating; Further stages.;
  • 20
  • C16H20N2O4 [ No CAS ]
  • [ 22265-37-8 ]
  • C33H42N6O8 [ No CAS ]
  • C33H42N6O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 48% 2: 30% Stage #1: C16H20N2O4; 4-methoxybenzamidine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Stage #2: In tetrahydrofuran Heating; Further stages.;
  • 21
  • C13H23N3O3 [ No CAS ]
  • [ 22265-37-8 ]
  • C16H21N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: C13H23N3O3; 4-methoxybenzamidine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Stage #2: In tetrahydrofuran Heating; Further stages.;
  • 22
  • [ 22265-37-8 ]
  • [ 95675-27-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 46 percent / Et3N / diethyl ether / 2 h / 0 - 5 °C 2: 53 percent / K2CO3, PbO2 / benzene / 0.03 h
  • 23
  • [ 22265-37-8 ]
  • [ 5466-70-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5-ethyl-2-methyl-pyridine 2: formic acid; Na2S2O4+2H2O / 190 - 200 °C
  • 24
  • [ 22265-37-8 ]
  • [ 70613-93-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: CHCl3 / 25 °C 2: aq. HBr, AcOH / Heating 3: (i) NaH, DMF, (ii) /BRN= 4272534/
  • 25
  • [ 22265-37-8 ]
  • [ 70552-22-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: CHCl3 / 25 °C 2: aq. HBr, AcOH / Heating
  • 26
  • [ 579-39-5 ]
  • [ 22265-37-8 ]
  • 5,5-bis(4-fluorophenyl)-2-(4-methoxyphenyl)-3,5-dihydro-4H-imidazol-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydroxide In ethanol; water at 80℃; for 8h; 1.2 Step 2. Preparation of 5,5-bis(4-fluorophenyl)-2-(4-methoxyphenyl)-3,5-dihydro-4H- imidazol-4-one A 50 ML round bottomed flask was charged with 4-methoxy-benzamidine (500 mg, 3.33 mmol) and difluorobenzil (820 mg, 3.33 mmol). The solids were dissolved in ETOH (20 ML) and a 2 N aq solution OF NAOH (5 ML) was added. The reaction flask was fitted with a condenser and heated to 80°C for 8 h. The reaction mixture was cooled to 23°C and then concentrated IIZ vacuo. The remaining solid was diluted with EtOAc (100 ML), washed with H2O (2 x 20 mL), and brine (15 mL). The organic layer was dried over NA2S04 and concentrated in vacuo. The crude oil was purified by flash column chromatography [ (35 g silica gel) 4: 1 Hex: EtOAc] to provide the desired product (943.8 mg, 75% yield) as a white POWDER.'H NMR (300 MHz, CD30D) : 8 10.20 (s, br, 1H), 8.00 (m, 2H), 7.57 (m, 3H), 7.23 (m, 2H), 6.95 (m, 6H), 3.80 (s, 3H); LC-MS RT = 3.04 min (M + H) + 379. 1 calc'd for C22HL7F2N202, found 379.2.
  • 27
  • [ 61072-56-8 ]
  • [ 105-45-3 ]
  • [ 22265-37-8 ]
  • [ 874120-06-6 ]
YieldReaction ConditionsOperation in experiment
36% With potassium acetate; In dimethyl sulfoxide; at 80℃; for 16h; A mixture of 4-(methyloxy)benzenecarboximidamide (3.0 g, 20.0 mmol), <strong>[61072-56-8]4-chloro-2-fluorobenzaldehyde</strong> (2.22 g, 14.3 mmol), methyl acetoacetate (2.0 g, 17.2 mmol), and potassium acetate (1.4 g, 14.3 mmol) was dissolved in DMSO (100 mL) with stirring, and heated at 80 C for 16 hours. The reaction mixture was diluted with ethyl acetate, washed with brine (3 x 100 mL), and dried (MgS04). The solvent was removed via rotovap and the residue was purified by ISCO silica column to afford a greenish solid product (2.0 g, 36 %). MS (ES+) m/z 390 [M+H]+.
  • 28
  • [ 459-57-4 ]
  • [ 6023-70-7 ]
  • [ 22265-37-8 ]
  • 4-(4-fluorophenyl)-N-1H-indazol-5-yl-6-methyl-2-[4-(methyloxy)phenyl]-1,4-dihydro-5-pyrimidinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With potassium acetate In dimethyl sulfoxide at 100℃; for 3h;
32% With potassium acetate In dimethyl sulfoxide at 100℃; for 3h; 1.2 A mixture of 4-(methyloxy)benzenecarboximidamide (50 mg, 0.33 mmol), 4-fluorobenzaldehyde (35 mg, 0.28 mmol), A/-1W-indazol-5-yl-3-oxobutanamide (60 mg, 0.28 mmol), and potassium acetate (55 mg, 0.56 mmol) was dissolved in DMSO (1 mL) with stirring, and heated at 100 °C for 3 hours. The reaction mixture was cooled to room temperature, poured into water (10 mL) to form a precipitate. The precipitate was filtered, washed with water, and purified by HPLC (RP, 25-75 % CH3CN/H20 with 0.05 M NH4HCO3) to afford the desired product (41 mg, 32 %) as a yellow solid. MS (ES+)m/z456[M+H]+.
  • 29
  • [ 22265-37-8 ]
  • [ 6851-99-6 ]
  • 2-(4-methoxyphenyl)-4-(2-nitrophenyl)-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile I EXAMPLE I STR32 EXAMPLE I STR32 A mixture of 2-bromo-2'-nitroacetophenone (18 g), 4-methoxybenzamidine (20 g), and silica gel (20 g) in acetonitrile (500 ml) is heated at 40° C. for 24 hours. The reaction is evaporated and the residue put on a layer of silica gel and eluted with 50% ethyl acetate/hexane (1500 ml). The solution is evaporated under reduced pressure to approximately 250 ml and extracted with 5% HCl (3*250 ml). The combined aqueous solution is basified with K2 CO3 and extracted with ethyl acetate (3*400 ml) to afford 2-(4-methoxyphenyl)-4-(2-nitrophenyl)-imidazole (17 g) as a dark yellow oil which is used in the next step without further purification.
  • 30
  • [ 141-97-9 ]
  • [ 22265-37-8 ]
  • [ 16858-19-8 ]
YieldReaction ConditionsOperation in experiment
8.58 g (75%) In chloroform; water 2.A Step A: Step A: Preparation of 6-hydroxy-4-methyl-2-p-methoxyphenylpyrimidine Under N2, a solution of ethyl acetoacetate (7.15 g, 0.053 mol) in CHCl3 (200 ml) was added dropwise to a suspension of 4-methoxybenzamidine in CHCl3 (200 ml). After stirring at room temperature overnight, water was added to the solution. The aqueous phase was separated and extracted with CHCl3 and the organic layers were combined, dried (Na2 SO4), filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product was eluted with 2% CH3 OH--CHCl3 to yield 8.58 g (75%) of product, m.p. 198°-199° C.
  • 31
  • [ 1105665-33-5 ]
  • [ 22265-37-8 ]
  • [ 1105662-75-6 ]
YieldReaction ConditionsOperation in experiment
In ethanol for 14h; Heating / reflux; 14.a 6-[1-Dimethylamino-meth-(E)-ylidene]-2-ethoxy-cyclohex-2-enone (WO 2004/104007) (1 g; 5 mmol) and 4-methoxybenzamidine (0.92 g; 6.1 mmol) are refluxed in EtOH (20 ml) for 14 hours. The reaction mixture is evaporated to dryness, taken up in CH2Cb and purified via chromatography (SiO2; acetone/hexanes 5:95) to yield the title compound as yellow resin. 1 H-NMR (400MHz; DMSO-d6): 8.58 (s, 1 H); 8.31 (d, 2H); 7.07 (d, 2H); 5.64 (t, 1 H); 3.93 (q, 2H); 3.84 (s, 3H); 2.78 (t, 2H); 2.40 (m, 2H); 1.40 (t, 3H). MS (m/z) ES+: 283 (MH+).
  • 32
  • [ 3240-35-5 ]
  • [ 6023-70-7 ]
  • [ 22265-37-8 ]
  • 4-[4-(aminosulfonyl)phenyl]-N-1H-indazol-5-yl-6-methyl-2-[4-(methyloxy)phenyl]-1,4-dihydro-5-pyrimidinecarboxamide [ No CAS ]
  • 33
  • [ 5398-77-6 ]
  • [ 6023-70-7 ]
  • [ 22265-37-8 ]
  • N-1H-indazol-5-yl-6-methyl-2-[4-(methyloxy)phenyl]-4-[4-(methylsulfonyl)phenyl]-1,4-dihydro-5-pyrimidinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium acetate In dimethyl sulfoxide at 100℃; for 3h;
  • 34
  • [ 61072-56-8 ]
  • [ 6023-70-7 ]
  • [ 22265-37-8 ]
  • 4-(4-chloro-2-fluorophenyl)-N-1H-indazol-5-yl-6-methyl-2-[4-(methyloxy)phenyl]-1,4-dihydro-5-pyrimidinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium acetate In dimethyl sulfoxide at 100℃; for 3h;
  • 36
  • [ 6023-70-7 ]
  • [ 22265-37-8 ]
  • [ 89763-93-9 ]
  • 4-[2-fluoro-4-(trifluoromethyl)phenyl]-N-1H-indazol-5-yl-6-methyl-2-[4-(methyloxy)phenyl]-1,4-dihydro-5-pyrimidinecarboxamide [ No CAS ]
  • 37
  • [ 1171113-63-5 ]
  • [ 22265-37-8 ]
  • [ 3424-93-9 ]
  • [ 1171113-80-6 ]
YieldReaction ConditionsOperation in experiment
48.5% With water; potassium hydrogencarbonate In tetrahydrofuran at 80℃;
  • 38
  • [ 367-86-2 ]
  • [ 22265-37-8 ]
  • [ 1224442-19-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In dimethyl sulfoxide at 110℃; for 0.5h; Microwave irradiation;
  • 39
  • [ 552-16-9 ]
  • [ 22265-37-8 ]
  • [ 1224442-32-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ortho-nitrobenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 4-methoxybenzamidine In N,N-dimethyl-formamide at 0 - 20℃;
  • 40
  • [ 3113-72-2 ]
  • [ 22265-37-8 ]
  • [ 1224442-33-4 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 5-methyl-2-nitrobenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 4-methoxybenzamidine In N,N-dimethyl-formamide at 0 - 20℃;
  • 41
  • [ 33844-21-2 ]
  • [ 22265-37-8 ]
  • [ 1224442-34-5 ]
  • 42
  • [ 446-34-4 ]
  • [ 22265-37-8 ]
  • [ 1224442-18-5 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In dimethyl sulfoxide at 110℃; for 0.5h; Microwave irradiation;
  • 43
  • [ 1493-27-2 ]
  • [ 22265-37-8 ]
  • 4-methoxy-N-(2-nitrophenyl)benzene carboximidamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In dimethyl sulfoxide at 110℃; for 0.5h; Microwave irradiation;
  • 44
  • [ 1239602-78-8 ]
  • [ 22265-37-8 ]
  • [ 1239602-83-5 ]
YieldReaction ConditionsOperation in experiment
87% In ethanol Reflux; 10 Example 10 Preparation of 2-(4-methoxyphenyl)-4-[2-((2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yloxy)-indan-5-yl]-pyrimidine (Compound 5C) A solution of 3-dimethylamino-1-[2-(3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yloxy)-indan-5-yl]-propenone (Compound E-27; 100 mg, 0.238 mmol) and 4-methoxybenzamidine (107 mg, 0.715 mmol) in EtOH (3 mL) was heated at reflux overnight. The mixture was concentrated to a solid which was purified by silica gel chromatography (1:1 CH2Cl2/EtOAc) to afford the title compound (105 mg, 87%): 1H NMR (CDCl3) δ 8.76 (d, J=5.2 Hz, 1H), 8.53 (d, J=9.0 Hz, 2H), 8.10 (d, J=8.7 Hz, 1H), 8.03-8.00 (m, 1H), 7.51 (d, J=5.4 Hz, 1H), 7.37 (d, J=8.0 Hz, 1H), 7.03 (d, J=9.0 Hz, 2H), 5.01 (m, 1H), 4.69 (m, 1H), 3.90 (s, 3H), 3.65-3.40 (m, 3H), 3.56 (s, 3H), 3.52 (s, 3H), 3.46 (s, 3H), 3.35-3.02 (m, 5H), 1.34 (d, J=6.2 Hz, 3H); ESIMS m/z 506 ([M+H]+, 100).
  • 45
  • [ 615-37-2 ]
  • [ 22265-37-8 ]
  • [ 32622-18-7 ]
YieldReaction ConditionsOperation in experiment
52% With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere;
  • 46
  • [ 353-85-5 ]
  • [ 22265-37-8 ]
  • [ 1309044-49-2 ]
YieldReaction ConditionsOperation in experiment
56% In acetonitrile at -196 - 60℃; Inert atmosphere;
  • 47
  • [ 22265-37-8 ]
  • [ 1309044-53-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / -196 - 60 °C / Inert atmosphere 2: hydrogenchloride / diethyl ether / Inert atmosphere
  • 48
  • [ 22265-37-8 ]
  • [ 1308251-14-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetonitrile / -196 - 60 °C / Inert atmosphere 2: hydrogenchloride / diethyl ether / Inert atmosphere 3: sulfur dichloride / acetonitrile / Reflux; Inert atmosphere
  • 49
  • [ 22265-37-8 ]
  • [ 1308251-19-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetonitrile / -196 - 60 °C / Inert atmosphere 2: hydrogenchloride / diethyl ether / Inert atmosphere 3: sulfur dichloride / acetonitrile / Reflux; Inert atmosphere 4: triphenylantimony / acetonitrile / 20 °C / Inert atmosphere
  • 50
  • [ 22265-37-8 ]
  • [ 289-96-3 ]
  • [ 69491-44-7 ]
YieldReaction ConditionsOperation in experiment
93% In acetonitrile at 25 - 60℃; for 2h; regioselective reaction;
  • 51
  • [ 420-04-2 ]
  • potassium 4-(methoxy)phenyltrifluoroborate [ No CAS ]
  • [ 22265-37-8 ]
YieldReaction ConditionsOperation in experiment
70% With palladium(II) trifluoroacetate; trifluoroacetic acid; 6-methyl-2,2'-bipyridine In methanol at 120℃; for 0.333333h; Microwave irradiation;
  • 52
  • [ 22265-37-8 ]
  • [ 3433-80-5 ]
  • [ 67205-04-3 ]
YieldReaction ConditionsOperation in experiment
72% With C24H22N6Ni; sodium t-butanolate In N,N-dimethyl-formamide at 100℃; for 36h; Inert atmosphere; Schlenk technique;
57% With copper(I) oxide; caesium carbonate; N,N`-dimethylethylenediamine In water at 100℃; for 40h; air;
  • 53
  • [ 75-15-0 ]
  • [ 22265-37-8 ]
  • 3-(4-methoxyphenyl)-1,2,4-thiadiazole-5-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With sodium methylate; sulfur In methanol for 24h; Inert atmosphere; Reflux; IV Scheme IV To a suspension of NH4CI (631 mg, 11.799mmol) in anhydrous toluene (12mL) at 0°C under nitrogen was slowly added AI(CH3)3solution (5.9mL, 2.0 in toluene) over 5 minutes. Suspension stirred at 0°C for 5 minutes and then slowly warmed to room temperature, stirring an additional 30 minutes at room temp. To this stirring solution was then added 4-methoxybenzonitrile (1.57g, 11.79mmol) in 2.5mL of toluene. The reaction was heated to 80°C. After 18 hours, the reaction solution was cooled to room temperature and was carefully poured into a slurry of Si02 (25g) in CHCI3 (60mL). After stirring for 10 minutes, the mixture was filtered and the filter cake was rinsed with MeOH (50mL). The filtrate was concentrated to give 1.43g (81%) of benzimidamide as a white solid, which was used without further purification. A suspension of benzimidamide (459mg, 3.056mmol), carbondisulfide (460mL, 7.62mmol) and sulfur (121mg, 3.774mmol) in MeOH (3.8ml_) was stirred under nitrogen at room temperature. To this was slowly added 1.9mL of sodium methoxide solution (25% w/v in MeOH). Upon complete addition, solution was heated to reflux. After 24 hours, the reaction solution was cooled to room temperature and the pH of the solution was adjusted to 4 with aqueous HCI (1 M). The yellow precipitate that formed was filtered and dried to afford 249mg (36%) of 3-(4-methoxyphenyl)-1,2,4-thiadiazole-5-thiol, which was used without further purification.
  • 54
  • [ 92427-19-5 ]
  • [ 22265-37-8 ]
  • [ 1438287-57-0 ]
YieldReaction ConditionsOperation in experiment
84% With caesium carbonate In ethylene glycol at 120℃; for 0.3h; Microwave irradiation; Green chemistry; regioselective reaction;
  • 55
  • [ 127956-11-0 ]
  • [ 22265-37-8 ]
  • [ 1450790-55-2 ]
  • 56
  • [ 7677-24-9 ]
  • [ 100-52-7 ]
  • [ 22265-37-8 ]
  • N-benzylidene-2-(4-methoxyphenyl)-4-phenyl-1H-imidazol-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With sodium sulfate In N,N-dimethyl-formamide for 0.166667h; Sealed tube; Microwave irradiation; Heating; 4.2 General procedure for the synthesis of scaffold 12, exemplified for 12a General procedure: In a sealed vessel, benzamidine (60 mg, 0.5 mmol) and sodium sulfate (284 mg, 2 mmol) were dissolved in 2.5 mL anhydrous DMF. Benzaldehyde (204 μL, 2 mmol) and TMSCN (133 μL, 1 mmol) were then added. The solution was microwave irradiated at 150 °C for 10 min. The solvent was removed in vacuo, and the crude product was purified by column chromatography employing either a Teledyne Isco chromatographic system (Hex/EtOAc) or an HPLC purification system (reverse phase, water/acetonitrile). Note: when compounds of generic structure 12 were purified by HPLC, acetonitrile traces were sometimes observed in the 1H NMR spectra (s, 2.10 ppm) and could not be removed despite prolonged rotary evaporation and oven-drying under vacuum.
  • 57
  • [ 98-03-3 ]
  • [ 7677-24-9 ]
  • [ 22265-37-8 ]
  • 2-(4-methoxyphenyl)-4-(thiophen-2-yl)-N-(thiophen-2-ylmethylene)-1H-imidazol-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With sodium sulfate In N,N-dimethyl-formamide for 0.166667h; Sealed tube; Microwave irradiation; Heating; 4.2 General procedure for the synthesis of scaffold 12, exemplified for 12a General procedure: In a sealed vessel, benzamidine (60 mg, 0.5 mmol) and sodium sulfate (284 mg, 2 mmol) were dissolved in 2.5 mL anhydrous DMF. Benzaldehyde (204 μL, 2 mmol) and TMSCN (133 μL, 1 mmol) were then added. The solution was microwave irradiated at 150 °C for 10 min. The solvent was removed in vacuo, and the crude product was purified by column chromatography employing either a Teledyne Isco chromatographic system (Hex/EtOAc) or an HPLC purification system (reverse phase, water/acetonitrile). Note: when compounds of generic structure 12 were purified by HPLC, acetonitrile traces were sometimes observed in the 1H NMR spectra (s, 2.10 ppm) and could not be removed despite prolonged rotary evaporation and oven-drying under vacuum.
  • 58
  • [ 100-83-4 ]
  • [ 22265-37-8 ]
  • 3-(4,6-bis(4-methoxyphenyl)-1,2-dihydro-1,3,5-triazin-2-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With sodium sulfate In N,N-dimethyl-formamide at 100℃; for 0.666667h; Sealed tube; Microwave irradiation; 4.5 General procedure for the synthesis of 13, exemplified for 13a General procedure: In a sealed vessel, benzamidine (120 mg, 1 mmol) and benzaldehyde (101 μL, 1 mmol) were dissolved in 1.5 mL anhydrous DMF. The solution was microwave irradiated at 100 °C for 40 min. The solvent was removed in vacuo, and the crude product was purified by column chromatography employing a Teledyne Isco chromatographic system (Hex/EtOAc). Note: Notwithstanding multiple attempts to remove them by chromatographic techniques, recrystallization from different solvents and scavenging, small traces of the starting aldehydes were sometimes detectable in the final compounds.
  • 59
  • [ 117-80-6 ]
  • [ 22265-37-8 ]
  • [ 1329681-59-5 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 4-methoxybenzamidine With sodium dodecyl-sulfate; potassium carbonate In water for 0.0833333h; Stage #2: 2,3-Dichloro-1,4-naphthoquinone In water at 70 - 80℃; for 8h; regioselective reaction; Representative procedure for synthesis: General procedure: 1 mmol nucleophile (2, 7 or 9) was added to 5 mL aqueous suspension of surfactant (0.5 mol % SDS). After stirring for five minutes, quinone 1 or 5 (1 mmol) was added and stirred at temperatures represented in Tables or Schemes. The products were filtered and purified after neutralization with 5% HCl, followed by column chromatography (if required) of the reaction mixture (hexane/EtOAc) leading to desired products.
  • 60
  • [ 22265-37-8 ]
  • [ 2216-94-6 ]
  • (Z)-4-benzylidene-2-(4-methoxyphenyl)-1H-imidazol-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tributylphosphine In toluene at 110℃; for 2h; Inert atmosphere;
  • 61
  • [ 51718-85-5 ]
  • [ 22265-37-8 ]
  • [ 1356003-65-0 ]
YieldReaction ConditionsOperation in experiment
76% With tributylphosphine In toluene at 110℃; for 2h; Inert atmosphere;
  • 62
  • [ 1736-31-8 ]
  • [ 22265-37-8 ]
  • (Z)-4-(4-fluorobenzylidene)-2-(4-methoxyphenyl)-1H-imidazol-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tributylphosphine In toluene at 110℃; for 2h; Inert atmosphere;
  • 63
  • [ 80220-94-6 ]
  • [ 22265-37-8 ]
  • (Z)-4-(2-methoxybenzylidene)-2-(4-methoxyphenyl)-1H-imidazol-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tributylphosphine In toluene at 110℃; for 2h; Inert atmosphere;
  • 64
  • [ 35283-11-5 ]
  • [ 22265-37-8 ]
  • (Z)-4-(4-(dimethylamino)benzylidene)-2-(4-methoxyphenyl)-1H-imidazol-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With tributylphosphine In toluene at 110℃; for 2h; Inert atmosphere;
  • 65
  • (3-methyl-3H-imidazol-4-yl)-propynoic acid ethyl ester [ No CAS ]
  • [ 22265-37-8 ]
  • (Z)-2-(4-methoxyphenyl)-4-((1-methyl-1H-imidazol-5-yl)methylene)-1H-imidazol-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tributylphosphine In toluene at 110℃; for 2h; Inert atmosphere;
  • 66
  • [ 1030-07-5 ]
  • [ 22265-37-8 ]
  • (Z)-4-([1,1′-biphenyl]-4-ylmethylene)-2-(4-methoxyphenyl)-1H-imidazol-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tributylphosphine In toluene at 110℃; for 2h; Inert atmosphere;
  • 67
  • [ 66869-70-3 ]
  • [ 22265-37-8 ]
  • (Z)-2-(4-methoxyphenyl)-4-(pyridin-2-ylmethylene)-1H-imidazol-5(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tributylphosphine In toluene at 110℃; for 2h; Inert atmosphere;
  • 68
  • [ 22265-37-8 ]
  • [ 609-15-4 ]
  • 5-chloro-2-(4-methoxyphenyl)-6-methylpyrimidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.8% With potassium <i>tert</i>-butylate In methanol at 0℃; for 4.5h; Reflux;
  • 69
  • [ 5373-87-5 ]
  • [ 22265-37-8 ]
YieldReaction ConditionsOperation in experiment
93% With hydrogen; nickel; acetic acid In methanol at 20℃; for 12h; 1 23-1:Take a 250 mL four-necked flask, add compound 22-1 (0.99 g, 3 mmol), and add 150 mL of MeOH.Add wet weight nickel 0.6g,Add to HOAc (3 mL) hydrogen atmosphere and stir at room temperature for 12 h.After the reaction is completed, the solution is desolvated, water is added, and the solid is precipitated.Obtained white solid, yield 93%
With mitochondrial amidoxime reducing component In aq. phosphate buffer at 37℃; Enzymatic reaction;
  • 70
  • [ 22265-37-8 ]
  • [ 22596-45-8 ]
  • [ 31483-79-1 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: 4-methoxybenzamidine With sodium methylate In methanol at 25℃; for 0.5h; Green chemistry; Stage #2: 2-methyl-2-nitro-3-phenyloxirane In methanol at 25℃; for 8h; Green chemistry;
  • 71
  • 5-methoxy-1,2,3-triazine [ No CAS ]
  • [ 22265-37-8 ]
  • 2-(4-methoxyphenyl)-5-methoxypyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% In acetonitrile at 90℃; for 24h; Inert atmosphere;
  • 72
  • 5-(N-acetylamino)-1,2,3-triazine [ No CAS ]
  • [ 22265-37-8 ]
  • N-(2-(4-methoxyphenyl)pyrimidin-5-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In acetonitrile at 90℃; for 72h; Inert atmosphere;
  • 73
  • 5-(methylthio)-1,2,3-triazine [ No CAS ]
  • [ 22265-37-8 ]
  • 2-(4-methoxyphenyl)-5-(methylthio)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In acetonitrile at 40℃; for 24h; Inert atmosphere;
  • 74
  • [ 13323-81-4 ]
  • [ 22265-37-8 ]
  • [ 100-51-6 ]
  • [ 78509-13-4 ]
YieldReaction ConditionsOperation in experiment
91% With platinum on activated charcoal; potassium <i>tert</i>-butylate In toluene for 24h; Reflux;
77% With [(4-(4-CF3)-Ph)Tr(NP(iPr)2)(NHP(iPr)2)Ir(cod)]; potassium hydroxide In tert-Amyl alcohol for 24h; Inert atmosphere; Reflux; regioselective reaction;
  • 75
  • [ 22265-37-8 ]
  • [ 2632-13-5 ]
  • [ 97978-70-6 ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate In acetonitrile at 0 - 80℃; 3; 12 Example 12: Synthesis of 2,4-Bis-(4-methoxy-phenyl)-1 H-imidazole 10 To a suspension of the commercially available 4-methoxythiobenzamide 8 (1 eq, 9.1 g, 60.59 mmol) in 200 mL of acetonitrile was added 25 g of K2C03 (3 eq, 181.78 mmol) and at 0°C 12.49 g of bromo-1 -(4-methoxyphenyl)-ethanone 9 (0.9 eq, 54.53 mmol). The mixture was stirred at 0°C for 8h then warmed to room temperature overnight. The reaction mixture was warmed to 80°C for 1 h, cooled to room temperature and filtered. The solid was washed with acetonitrile then triturated with water and filtered to give 12.6 g of 2,4-Bis-(4-methoxy-phenyl)-1 H-imidazole (74% yield). 1 H NMR (400 MHz, DMSO-d6) δ ppm 12.35 (br. s., 0.7 H) 12.22 (br. s, 0.3 H) 7.95 (d, J=8.8 Hz, 2 H) 7.76 (d, J=8.0 Hz, 1.4 H) 7.68 (br. s, 0.6 H) 7.56 (s, 0.7 H) 7.28 (br. s., 0.3 H) 7.03 (d, J=8.8 Hz, 2 H) 6.94 (d, J=8.0 Hz, 2 H) 3.81 (s, 3 H) 3.77 (s, 3 H) (2 tautomer's forms 70/30) LCUV-MS: Rt = 1.64 min m/z = 281 (method 5)
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