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CAS No. : | 56643-85-7 | MDL No. : | MFCD06660785 |
Formula : | C10H11N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DGHAOTHIDTUSJY-UHFFFAOYSA-N |
M.W : | 173.21 | Pubchem ID : | 1265319 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 52.38 |
TPSA : | 43.84 Ų |
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) : | -6.7 cm/s |
Log Po/w (iLOGP) : | 1.37 |
Log Po/w (XLOGP3) : | 0.92 |
Log Po/w (WLOGP) : | 1.52 |
Log Po/w (MLOGP) : | 0.75 |
Log Po/w (SILICOS-IT) : | 1.12 |
Consensus Log Po/w : | 1.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.99 |
Solubility : | 1.78 mg/ml ; 0.0103 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.43 |
Solubility : | 6.49 mg/ml ; 0.0375 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.97 |
Solubility : | 0.186 mg/ml ; 0.00108 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.2 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With hydrogenchloride; zinc; In ethanol; water; for 1h;Reflux; | 1-(4-nitrobenzyl)-1H-imidazole (1) (7.11 g, 0.035 mol) wasdissolved in ethanol (100 mL) and 25% HCl (100 mL) mixture.Zinc powder (39.49 g, 0.35 mol) was divided into tenequal portions and each portion was added to the stirringsolution in 15 min intervals. Once the addition of the zincwas completed, reaction mixture was refluxed for 1 h. Hotsolution was allowed to cool down, poured into ice waterand then neutralized by using 10% NaOH solution. The precipitatewas extracted with ethyl acetate (3100 mL). The extracts were combined and filtered over anhydrous Na2SO4.The solvent was evaporated and the residue was recrystallized from ethanol to give the 1-(4-aminobenzyl)-1H-imidazole(2). Yield: 67%; m.p. 126 C. Literature m.p. 127 C.[32] |
With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; ethyl acetate; at 20℃; under 2550.26 Torr; | A solution of H-5a (2.1 g, 10 mmol) in 10 mL ethanol, 10 mL ethyl acetate and 13 mL 1 M hydrochloric acid is combined with palladium (10% on activated charcoal, 0.27 g) in a hydrogenation reactor and stirred overnight at RT under 3.4 bar hydrogen pressure. The reaction mixture is filtered, evaporated down and codistilled three times with ethanol. Yield: 1.8 g. | |
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 760.051 Torr; for 4.5h; | Potassium carbonate (2.00 g; 14.6 mmol) was added to a stirred solution of 1-(bromomethyl)-4-nitrobenzene (3.20 g; 14.8 mmol) and imidazole (1.00 g; 14.7 mmol) in acetonitrile (60 mL). The mixture was stirred at room temperature for 17 hr and then concentrated under reduced pressure. The residue was partitioned between EA and water and the phases separated. The aqueous phase was extracted twice with EA; and the combined organic layers washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 1-(4-nitrobenzyl)-1H-imidazole (1.27 g) as a red/brown oil. A solution of 1-(4-nitrobenzyl)-1H-imidazole (2.67 g; 13.1 mmol) in ethanol (100 mL) was hydrogenated at atmospheric pressure with 10% palladium on carbon (0.285 g) at room temperature for 4.5 hr. The mixture was filtered through diatomaceous earth and then concentrated under reduced pressure to give 4-[(1H-imidazol-1-ylmethyl]benzenamine (2.24 g) as a white solid. |
With hydrogen;palladium 10% on activated carbon; In ethanol; for 0.583333h; | To a nitrogen purged solution of l-[(4- nitrophenyl)methyl]imidazole (0.8 g, 3.98 mmol) in EtOH (10 mL) was added 10% Pd/C (0.08 g). The reaction mixture was flushed with H2 (g) for 5 min and stirred for 0.5 h. The reaction mixture was filtered through Celite and concentrated under reduced pressure to afford the title compound. 1H NMR (DMSO- e) δ 7.65 (s, 1H), 7.10 (t, 1H), 6.97 (dt, 2H), 6.85 (t, 1H), 6.51 (dt, 2H), 5.11 (s, 2H), 4.94 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36.2 1-(4-aminobenzyl)-1H-imidazole: The experimental protocol used is the same as that described for intermediate 33.2, 1-(4-nitrobenzyl)-1H-imidazole replacing 1-(4-aminophenyl)-1H-imidazole. Pale yellow powder. Melting point: 121-122 C. NMR 1H (CDCl3, 100 MHz, δ): 2.87 (wide s, 2H, NH2), 4.98 (s, 2H, CH2), 6.88 (m, 1H, H imidazole), 7.06 (m, 1H, H imidazole), 7.52 (m, 1H, H imidazole), 6.60-6.69-6.95-7.05 (4s, 4H, arom. H). | ||
EXAMPLE 4 N-[p-(1-Imidazolylmethyl)phenyl]alanine ethyl ester dihydrochloride In a 200 ml round-bottom flask is placed a solution of 8.0 g of p-(1-imidazolylmethyl)aniline prepared as described in Reference Example 3, and 30 ml of formic acid in 80 ml of toluene. The flask was fitted with a water separator, and the solution was refluxed for 4 hours. | ||
36.2 1-(4-aminobenzyl)-1H-imidazole The experimental protocol used is the same as that described for intermediate 33.2, 1-(4-nitrobenzyl)-1H-imidazole replacing 1-(4-aminophenyl)-1H-imidazole. Pale yellow powder. Melting point: 121-122 C. NMR 1H (CDCl3, 100 MHz, δ): 2.87 (wide s, 2H, NH2), 4.98 (s, 2H, CH2), 6.88 (m, 1H, H imidazole), 7.06 (m, 1H, H imidazole), 7.52 (m, 1H, H imidazole), 6.60-6.69-6.95-7.05 (4s, 4H, arom. H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; N,N-dimethyl-formamide; at 160℃; for 0.333333h;Microwave irradiation; | [0323] A mixture of intermediate 33 (0.10 g, 0.28 mmol), 4-imidazol-l-ylmethyl- phenylamine (60 mg, 0.35 mmol), Pd2(dba)3 (25 mg, 0.027 mmol), Xantphos (30 mg, 0.052 mmol) and cesium carbonate (0.20 g, 0.61 mmol) in dioxane/DMF (3/1, 4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 C for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered. The filtered solid was washed with DCM, the filtrate concentrated and the residue purified by HPLC. The corrected fractions were combined and poured into saturated NaHCO3 solution (30 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and then taken up in minimum amount of EtOAc. Hexanes were added until solid precipitated. After filtration, the title compound was obtained as a white solid (40 mg, 29%).[0324] 1H NMR (500 MHz, DMSO-d6): δ 1.12 (s, 9H), 2.13 (s, 3H), 5.07 (s, 2H), 6.89 (s, IH), 7.12 (d, J= 8.6 Hz, 2H), 7.15 (s, IH), 7.46 (t, J= 7.9 Hz, IH), 7.49-7.52 (m, IH), 7.56 (s, IH), 7.63 (d, J= 8.6 Hz, 2H), 7.72 (s, IH), 7.94 (s, IH), 8.09 (s, IH), 8.14 (d, J= 8.1 Hz, IH), 8.60 (s, IH), 9.02 (s, IH). MS (ES+): m/z 492 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of sodium nitrite (0.77 g, 10 mmol) in 5 mL water is added at -10 C. to a solution of H-5b (1.8 g, 10 mmol) in 10 mL 37% hydrochloric acid. After 20 min stirring at 0 C. a solution of tin(II)chloride dihydrate (8.9 g, 39 mmol) in 10 mL 37% hydrochloric acid is again added at -10 C. The reaction mixture is heated to RT, made basic with 10 N sodium hydroxide solution and extracted with ethyl acetate. The aqueous phase is filtered and extracted with dichloromethane. The combined organic phases are dried and evaporated down. Yield: 0.32 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In N,N-dimethyl acetamide; at 20℃; | A mixture of (2E)-3- [5- (4-fluorophenyl)-l-methyl-lH- PYRAZOL-4-YL] ACRYLIC acid (1.0 g), oxalyl chloride (618 mg), tetrahydrofuran (60 ML) AND N, N-dimethylformamide (2 drops) was stirred at room temperature for 2 hrs. The reaction mixture was concentrated and diluted with N, N-dimethylacetamide (50 mL). 4- (LH-IMIDAZOL-1-YLMETHYL) aniline (844 mg) was added and the mixture was stirred overnight at room temperature. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MGSO4) and concentrated. The obtained solid was recrystallized from acetone-hexane to give (2E)-3- [5- (4- FLUOROPHENYL)-1-METHYL-LH-PYRAZOL-4-YL]-N- [4- (LH-IMIDAZOL-1- YLMETHYL) PHENYL] ACRYLAMIDE as pale-yellow prism crystals (1.41 g, yield 86%). melting point: 213-214C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In N,N-dimethyl-formamide; | 4.6 3-{(Z)-1-[4-((imidazol-1-yl)methyl)anilino]-1-phenylmethylidene}-5-nitro-2-indolinone Prepared from 3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone and 1.5 equivalents of 4-(imidazol-1-yl)methyl-aniline (melting point: 128-130 C.) in DMF (120 C., 1 hour), pouring into water and washing the precipitate with MeOH and ether. Yield: 90% of theory; Melting point: 355 C.; C25 H19 N5 O3; Calc.: C, 68.64; H, 4.38; N, 16.01; Found: 68.35; 4.51; 15.92; Calc.: molar peak M+ =437; Found: molar peak M+ =437. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2 parts (14.4%) | In methanol; water; ethyl acetate; | Example 18 To a stirred and heated (100 C.) solution of 10 parts of 4-(1H-imidazol-1-ylmethyl)benzenamine in 50 parts of poly phosphoric acid were added 15 parts of ethyl 3-oxobutanoate. The whole was stirred for 4 hours at 140 C. 100 Parts of water were added to the mixture and the whole was neutralized with potassium carbonate. The product was extracted with a mixture of ethyl acetate and methanol. The extract was dried, filtered and concentrated. The concentrate was crystallized from a mixture of 2-propanone and methanol. The product was filtered off and dried, yielding 2 parts (14.4%) of 6-(1H-imidazol-1-ylmethyl)-2-methyl-4(1H)quinolinone; mp. 245.5 C. (decomp.) (compound 51). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.8 parts (74.8%) | In 1,2-dichloro-ethane; | EXAMPLE 11 To a stirred solution of 10 parts of <strong>[56643-85-7]4-[(1H-imidazol-1-yl)methyl]benzenamine</strong> in 180 parts of 1,2-dichloroethane were added dropwise 3.9 parts of 4-methylene-2-oxetanone. After stirring for 1/2 hour at room temperature, the precipitate was filtered off, washed with 1,2-dichloroethane and dried, yielding 9.8 parts (74.8%) of N-[4-(1H-imidazol-1-ylmethyl)phenyl]-3-oxobutanamide; mp. 175 C.(interm. 57). In a similar manner there were also prepared the intermediates listed in Table 4: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 5 N-[p-(1-Imidazolylmethyl)phenyl]glycine ethyl ester dihydrochloride In the same procedure as described in Example 4, N-[p-(1-imidazolylmethyl)phenyl]glycine ethyl ester dihydrochloride was prepared from p-(1-imidazolylmethyl)aniline which was prepared as described in Reference Example 2, and ethyl bromoacetate. M.P.: 156-159 C. (decomp.) (pale yellow prisms; recrystallized from ethanol-diethyl ether). IR-Absorption Spectrum (KBr): νCO 1740 cm-1. NMR Spectrum (DMSO-D6): δ1.17 (t, 3H), 3.92 (s, 2H), 4.10 (q, 2H), 5.27 (s, 2H), 6.62 (d, 2H), 7.0-8.0 (m, 7H), and 9.35 (m, 1H). Elemental Analysis as C14 H19 O2 N3 Cl2: Calcd. C, 50.61; H, 5.76; N, 12.65. Found C, 50.33; H, 5.78; N, 12.51. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;palladium; In ethanol; dichloromethane; toluene; | REFERENCE EXAMPLE 2 p-(1-Imidazolylmethyl)aniline A mixture of 13.6 g of imidazole, 43.2 g of p-bromomethylnitrobenzene and 55.2 g of anhydrous potassium carbonate in 300 ml of dry toluene was refluxed for 18 hours. After concentration under reduced pressure, 200 ml of dichloromethane was added to the residue and insoluble salts were filtered off. The filtrate was evaporated and the residue was chromatographed on silica gel using dichloromethane-ethanol (20:1 by volume) to give 27.9 g of p-(1-imidazolylmethyl)nitrobenzene as pale yellow platelets. Then, a solution of 2.0 g of this product in 50 ml of ethanol was hydrogenated over 0.2 g of palladium on carbon at room temperature under a hydrogen pressure of 4 atms. After filtration and evaporation, the residual solid was recrystallized from ethanol-diethyl ether-petroleum ether to give 1.4 g of p-(1-imidazolylmethyl)aniline as colorless needles. M.P.: 134-137 C. IR-Absorption Spectrum (KBr): νNH 3300 cm-1 and 3450 cm-1. NMR Spectrum (CDCl3): δ3.96 (br, 2H), 5.01 (s, 2H), 6.70 (d, 2H), 6.95 (t, 1H), 7.04 (d, 2H), 7.12 (m, 1H), and 7.59 (br-s, 1H). Elemental Analysis as C10 H11 N3: Calcd. C, 69.34; H, 6.40; N, 24.26. Found C, 69.23; H, 6.41; N, 24.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A cooled (0 0C) solution of 6-(cyclopropylmethyl(propyl)amino)pyhmidine-4- carboxylic acid (Intermediate 21 , 112 mg; 0.45 mmol) in DCM was treated with diisopropylethylamine (78.4 mL; 0.52 mmol) and methyl chloroformate (36.2 mL; 0.47 mmol). After stirring at 0 0C for 15 minutes, 4-(1 H-imidazol-1- ylmethyl)aniline (Maybridge, 117 mg; 0.67 mmol) was added and the mixture stirred for 72 hours. The solvent was evaporated and the compound purified by preparative HPLC to give the title compound as a white solid. 1H NMR (400MHz, CDCI3) δ 10.01 (1 H, s), 8.56 (1 H, s), 7.76 (2H, d, J = 8.2 Hz), 7.55 (1 H, s), 7.35 (1 H, s), 7.19 (2H, d, J = 8.2 Hz), 7.09 (1 H, s), 6.91 (1 H, s), 5.11 (2H, s), 3.52 (4H, s), 1.75-1.60 (2H, m), 1.08 (1 H, m), 0.96 (3H, t, J = 7.3 Hz), 0.57 (2H, d, J = 7.7 Hz), 0.35-0.29 (2H, m). MS (ESI+) 391. HPLC (Condition C) Rt 2.32 min (HPLC purity 99.7%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | With tri-tert-butyl phosphine; potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; N,N-dimethyl-formamide; toluene; at 160℃; for 0.5h;Microwave irradiation; | A mixture of 1 (0.155 g, 0.622 mmol), 4-imidazol- 1-ylmethyl-phenylamine (0.14 g, 0.809 mmol), Pd2(dba)3 (0.057 g, 0.062 mmol), tri-te/t-butyl-phosphine (IM in toluene, 0.125 mL, 0.13 mmol) and potassium tert-butoxide (0.350 g, 3.11 mmol) were suspended in dioxane (2 mL) and DMF (2 mL) and microwaved at 160 0C for 30 min. The reaction mixture was cooled to room temperature, diluted with DCM (30 mL), filtered and concentrated in vacuo. ηPLC purification afforded the title compound (0.015 g, 6%).[0435] 1H NMR (500 MHz, DMSO-J6): δ 2.32 (s, 3H), 5.01 (s, 2H), 6.85 (d, J = 2.6 Hz, IH), 6.89 (s, IH), 7.18-7.22 (m, 3H), 7.29-7.30 (m, IH), 7.39 (s, IH), 7.74 (s, IH), 7.87 (d, J = 8.6 Hz, 2H), 7.91 (s, IH), 9.26 (s, IH), 11.6 (s, IH)MS (ES+): m/z 387 (M+H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 90℃; for 14h;Inert atmosphere; | 5-(2-Chloropyrimidin-4-yl)-2-(tetrahydro-2H-pyran-4- yloxy)benzonitrile (0.10 g, 0.31 mmol), 4-(imidazol-l-ylmethyl)aniline (0.08 g, 0.47 mmol), cesium carbonate (0.31 g, 0.95 mmol), Pd(OAc)2 (0.10 g, 0.05 mmol) and BINAP (0.05 g, 0.08 mmol) and toluene (10 mL) were added to a flask and the reaction mixture sparged with nitrogen (3 min). The reaction mixture was placed in an oil bath at 90 C and stirred for 14 h. The reaction was cooled to rt, H20 (5.0 mL) and EtOAc (25 mL) were added, the aqueous layer extracted with EtOAc (3 x 15 mL), the organic layers combined, dried over sodium sulfate, filtered and evaporated. Purification by column chromatography (Hexanes/EtOAc to EtOAc/ 10% MeOH/CH2Cl2 with 1% NH4OH) followed by recrystallization/precipitation from Hexanes/EtOAc afforded the title compound (0.035 g, 25%). 1H NMR (DMSO- e) δ 10.1 (br s, 1H), 8.62 (d, 2H), 8.48 (s, 1H), 7.90 (s, 1H), 7.72 (d, 1H), 7.59 (t, 2H), 7.39 (d, 1H), 4.98-4.96 (m, 1H), 3.90-3.86 (m, 2H), 3.88 (s, 3H), 3.76 (s, 3H), 3.59-3.56 (m, 2H), 2.08-2.03 (m, 2H), 1.69 (m, 2H); TOF [M+H]+ 461.1816. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 100℃; for 1h; | mixture of Example 1E (0.060 g, 0.167 mmol) and <strong>[56643-85-7]4-((1H-imidazol-1-yl)methyl)aniline</strong> (0.046 g, 0.267 mmol) was heated in a capped vial at 100 C. for 1 hour. The reaction mixture was treated with ethyl acetate and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered, and concentrated. The crude material was purified on a 12 g column using the ISCO Companion flash system eluting with methanol/ethyl acetate (5:95 to 10:90) to provide the title compound. 1H NMR (400 MHz, CD3OD) δ 5.23 (s, 2H), 7.00 (s, 1H), 7.04 (d, J=1.9 Hz, 1H), 7.14 (s, 1H), 7.35-7.29 (m, 2H), 7.61-7.51 (m, 3H), 7.71-7.64 (m, 1H), 7.87-7.75 (m, 4H), 9.14 (s, 1H). MS (ESI+) m/z 468.8 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With trifluoroacetic acid; at -15 - 20℃; for 40h;Inert atmosphere; | Cooled (-15 C) trifluoroacetic acid (40 mL) was added to 2 (2 g, 11.547 mmol) at -15 C then paraformaldehyde (0.55 g, 18.46 mmol) added to the reaction mixture at same temperature and stirred for 40 h at RT, reaction progress was monitored by TLC. After completion of the reaction, the reaction mixture was poured into crushed ice (150 g), then 30% aq ammonia solution (40 mL) was added to the reaction mixture (until pH = 9-10) then extracted with dichloromethane (3 × 15 mL) and the organic extract was washed with brine solution, dried over an anhydrous Na2SO4, organic solvent was evaporated under reduced pressure to result crude gummy compound. Crude compound was purified by column chromatography (100-200 silica gel) and the desired product 3 was eluted by 8% MeOH: DCM as a yellow solid. Yield: 45% (based on 2). M.p., 194-196 C (decomp). HRMS (Calcd. for C23H22N6 is 382.1906): 383.1954 (M + H molecular ion peak). 1H NMR (CDCl3, 400 MHz): δ 7.45 (s, 2H, ImH), 7.07-7.09 (d, J = 8.2 Hz, 2H, ArH), 7.02 (s, 2H, ArH), 6.94-6.96 (dd, J = 1.6, 6.6 Hz, 2H, ArH), 6.83 (s, 2H, ImH), 6.65 (s, 2H, ImH), 4.95 (s, 4H, ArCH2-Im), 4.59-4.63 (d, J = 16.8 Hz, 2H, exo CH), 4.24 (s, 2H, NCH2N), 4.05-4.09 (d, J = 16.8 Hz, 2H, endo CH) ppm. 13C NMR (CDCl3, 100 MHz): δ 147.9, 137.1, 131.7, 129.5, 128.1, 126.4, 125.7, 125.5, 119.1, 66.6, 58.4, 50.2 ppm. FT-IR (neat, ῡ) 3108(w), 3043(w), 2945(w), 1613(m), 1575(w), 1494(s), 1439(m), 1280(m), 1206(m), 1072(m) cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; dichloromethane; at 20℃; for 4h; | Procedure for synthesis of compound 88. A mixture of compound 86 (128 mg, 0.44mmol, 1.00 eq.), 4-imidazol-l-ylmethyl-phenylamine (87) (92 mg, 0.53 mmol, 1.2 eq.), TBTU (241 mg, 0.75 mmol, 1.7 eq.), triethylamine (0.2 mL, 1.44 mmol, 3.3 eq.), DCM (3 mL) and THF (5 mL) was stirred at room temperature for 4 hours, diluted with equal volume of saturated aqueous NaHC03 solution and stirred at room temperature for 2 hours. The resulting mixture was extracted with DCM. The organic phase was dried over sodium sulfate and concentrated at reduced pressure. The obtained residue was purified by column chromatography (silica gel, ethyl acetate/MeOH, 20: 1) giving compound 88 (80 mg, 41%) as a yellowish solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; acetonitrile; at 20℃; for 24h; | Example 106 5-(4-((4-((1H-imidazol-1-yl)methyl)phenyl)amino)-1,3,5-triazin-2-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile To an appropriate sized microwave vial, 5-(4-chloro-1,3,5-triazin-2-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile (50 mg, 0.158 mmol) and <strong>[56643-85-7]4-((1H-imidazol-1-yl)methyl)aniline</strong> (33 mg, 0.189 mmol) were dissolved in acetonitrile (1.5 ml) and N,N-dimethylformamide (1.5 ml) and stirred at room temperature for 24 hr. The mixture was purified via preparative HPLC (10-95% acetonitrile in water, 0.1% trifluoroacteic acid buffer). Clean fractions poured into a saturated solution of sodium bicarbonate in water and extracted with dichloromethane. Organic layer was dried over Mg2SO4 and evaporate under reduces pressure to yield 5-(4-((4-((1H-imidazol-1-yl)methyl)phenyl)amino)-1,3,5-triazin-2-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile. 1H NMR (400 MHz, DMSO-d6) δ 10.37 (s, 1H), 8.80 (s, 1H), 8.62-8.50 (m, 2H), 7.82-7.68 (m, 3H), 7.56 (d, J=9.6 Hz, 1H), 7.27 (d, J=8.2 Hz, 2H), 7.17 (s, 1H), 6.88 (s, 1H), 5.15 (s, 2H), 4.97-4.9 (m, 1H), 3.91-3.83 (m, 2H), 3.61-3.50 (m, 2H), 2.08-1.96 (m, 2H), 1.74-1.62 (m, 2H). LCMS-ESI+ (m/z): [M+H]+ calcd for C25H23N7O2: 454.19. found: 454.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.5% | With trifluoroacetic acid; In iso-butanol; at 100℃; | General procedure: A flask was charged with compound 10a-c (0.70 mmol), 11a-g (0.70 mmol), TFA (0.08 mL, 1.05 mmol), and 2-BuOH (10 mL). The slurry was heated to 100 C for 5 h. The reaction mixture was allowed to cool to room temperature and was neutralized with a saturated aqueous sodium bicarbonate solution. The aqueous mixture was then extracted with CH2Cl2 (20 mL) three times. The crude product was purified using flash chromatography with dichloromethane/methanol (v/v, 1:1) as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36.7% | With trifluoroacetic acid; In iso-butanol; at 100℃; | General procedure: A flask was charged with compound 10a-c (0.70 mmol), 11a-g (0.70 mmol), TFA (0.08 mL, 1.05 mmol), and 2-BuOH (10 mL). The slurry was heated to 100 C for 5 h. The reaction mixture was allowed to cool to room temperature and was neutralized with a saturated aqueous sodium bicarbonate solution. The aqueous mixture was then extracted with CH2Cl2 (20 mL) three times. The crude product was purified using flash chromatography with dichloromethane/methanol (v/v, 1:1) as eluents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38.9 mg | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 10 - 35℃;Inert atmosphere; | Example 275 (2E)-N-(4-(1H-Imidazol-1-ylmethyl)phenyl)-3-(4-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)acrylamide HATU (118 mg) was added to a mixture of (2E)-3-(4-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl)acrylic acid (50 mg), <strong>[56643-85-7]4-((1H-imidazol-1-yl)methyl)aniline</strong> (36 mg), DIEA (0.109 mL) and DMF (1 mL) at room temperature, and the resulting mixture was stirred overnight under nitrogen atmosphere at the same temperature. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane). The obtained solid was washed with IPE to obtain the title compound (38.9 mg). 1H NMR (300 MHz, DMSO-d6) δ 3.93 (3H, s), 5.29 (2H, s), 6.27 (1H, t, J=2.0 Hz), 6.84 (1H, d, J=15.6 Hz), 7.21 (2H, d, J=8.7 Hz), 7.43-7.52 (2H, m), 7.62-7.82 (5H, m), 8.08 (1H, s), 8.52 (1H, d, J=5.1 Hz), 8.77 (1H, s), 10.32 (1H, s). |
38.9 mg | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | At room temperature,HATU (118 mg)Add to(2E) -3- (4- (1-methyl-1H-pyrazol-4-yl) pyridin-3-yl)4 - ((1H-imidazol-1-yl) methyl) aniline (36 mg)A mixture of DIEA (0.109 mL) and DMF (1 mL)The resulting mixture was stirred in a nitrogen atmosphere,Stir at room temperature overnight.After removal of the solvent by distillation under reduced pressure, the residue was purified by silica gel column chromatography (NH, ethyl acetate / hexane).The resulting solid was washed with IPE to give the title compound (38.9 mg). |
Tags: 56643-85-7 synthesis path| 56643-85-7 SDS| 56643-85-7 COA| 56643-85-7 purity| 56643-85-7 application| 56643-85-7 NMR| 56643-85-7 COA| 56643-85-7 structure
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