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Chemical Structure| 51746-85-1 Chemical Structure| 51746-85-1

Structure of 51746-85-1

Chemical Structure| 51746-85-1

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Product Details of [ 51746-85-1 ]

CAS No. :51746-85-1
Formula : C8H7N3
M.W : 145.16
SMILES Code : C1(C2=CNC=N2)=CC=CN=C1
MDL No. :MFCD10565593
InChI Key :YFOKBFRTGLSZLU-UHFFFAOYSA-N
Pubchem ID :3040177

Safety of [ 51746-85-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 51746-85-1 ]

* 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 [ 51746-85-1 ]

[ 51746-85-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 859076-83-8 ]
  • [ 51746-85-1 ]
  • 2
  • [ 51746-85-1 ]
  • 3-(1(3)<i>H</i>-imidazol-4-yl)-piperidine [ No CAS ]
  • 5
  • [ 51746-85-1 ]
  • [ 251354-75-3 ]
  • 5-methyl-1<i>H</i>-pyrrole-2-carboxylic acid 5-hydroxy-3-methoxy-2,2-dimethyl-6-{8-methyl-2-oxo-4-[2-(4-pyridin-3-yl-imidazol-1-yl)-ethoxy]-2<i>H</i>-chromen-7-yloxy}-tetrahydro-pyran-4-yl ester [ No CAS ]
  • 6
  • [ 2302-25-2 ]
  • [ 1692-25-7 ]
  • [ 51746-85-1 ]
  • 7
  • [ 96-49-1 ]
  • [ 51746-85-1 ]
  • [ 401522-20-1 ]
  • 8
  • [ 51746-85-1 ]
  • [ 100-39-0 ]
  • 3-(1-benzyl-1H-imidazol-4-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% [0338] 3-benzyl-lH-imidazol-4-ylpyridine (60). To a solution of 34 (35 mg, 0.25 mmol) in THF (5 mL) under argon was added sodium hydride (12 mg, 0.29 mmol) in one portion and the resultant slurry was stirred for 20 min. Benzyl bromide (26 uL, 0.32 mmol) was added and the resultant solution was stirred for 10 min. The reaction was quenched by the slow addition of HCl (aq) (1 N, 2 mL), diluted with 13 mL of water and washed with ethyl acetate (3 x 15 ml). Dichloromethane was added (25 mL) and the aqueous fraction was adjusted to pH 9 with NaOH (aq) (10 N). The organic fraction was collected and the aqueous was extracted with dichloromethane (20 mL), the combined organic fractions were dried (Na2S04), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (CH30H/CHC13, 2.5/97. 5, Rf= 0.26) to afford the title compound 60 (43 mg, 74% yield) as a white semisolid : 1H NMR (CDC13) 8 8.95 (br s, 1H), 8.47 (br s, 1H), 8.10 (m, 1H) 7.64 (m, 1H) 7.42-7. 17 (m, 7H) 5.17 (s, 2H); LRMS (ESI) nilz calcd for C15Hl4N3 [M + H]+ 236, found 236; HRMS (ESI) nilz calcd for C15Hl4N3 [M + H] + 236.1188, found 236.1198 ; HPLC > 99% (tR = 10 min, 60 (A): 40 (B): 0. 02 (C); tR = 6. 12 min, 60 (A): 40 (B): 0. 07 (C)).
  • 9
  • [ 51746-85-1 ]
  • [ 75-03-6 ]
  • 3-(1-ethyl-1H-imidazol-4-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% [0337] 3-Ethyl-lH-imidazol-4-yl) pyridine (59). To a solution of 34 (36 mg, 0.25 mmol) in THF (5 mL) under argon was added sodium hydride (12 mg, 0.29 mmol) in one portion and the resultant slurry was stirred for 20 min. Iodoethane (26 pL, 0. 32 mmol) was added and the resultant solution was stirred for 10 min. The reaction was stopped by the careful addition of aqueous hydrochloric acid (1 N, 2 mL), diluted with 13 mL of water and washed with ethyl acetate (3 x 15 ml). Dichloromethane was added (25 mL) and the aqueous was adjusted to pH 9 with NaOH (aq) (10 N). The organic fraction was collected and the aqueous fraction was extracted with dichloromethane (20 mL), the combined organic fractions were dried Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (CH30H/CHC13, 2.5/97. 5, Rf= 0.27) to afford the title compound 59 (34 mg, 79% yield) as a clear oil :'H NMR (CDCl3) 5 8.93 (m, 1H), 8.44 (m, 1H), 8.07 (m, 1H), 7.54 (br s, 1H), 7.28 (m, 2H), 4.02 (q, J= 7.4 Hz, 2H), 1.49 (t, J= 7.4 Hz, 3H); LRMS (ESI) m/z calcd for GioHnNs [M + H] + 174, found 174; HRMS (ESI) mlz calcd for CloHllN3 [M + H] + 174. 1031, found 174.1042 ; HPLC > 97% (tR = 13. 28 min, 60 (A): 40 (B): 0.02 (C); tR= 3. 67 min, 80 (A): 20 (B): 0. 1 (C).
  • 10
  • [ 51746-85-1 ]
  • [ 74-88-4 ]
  • 3-(1-methyl-1H-imidazol-4-yl)pyridine [ No CAS ]
  • [ 859239-29-5 ]
YieldReaction ConditionsOperation in experiment
[0336] 3- (1-Methyl-LH-imidazol-4-yl) pyridine and 3- (1-methyl-1H imidazol-5- yl) pyridine (58a, b). To a solution of 34 (37 mg, 0.26 mmol) in THF (4 mL) under argon was added sodium hydride (11 mg, 0.28 mmol) in one portion and the resultant slurry was stirred for 5 min. Iodomethane (190 pL, 0.31 mmol) was added and the resultant solution was stirred for 10 min. The reaction was stopped by the careful addition of aqueous hydrochloric acid (0.25 N, 6 mL) and washed with ethyl ether (3 x 10 ml). The aqueous fraction was adjusted to pH 9 with NaOH (aq) (10 N) and extracted with ethyl ether (3 x 30 mL), dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (CH30H/CHCl3, 2.5/97. 5, Rf= 0.15) to afford the title compounds 58a, b as an inseparable mixture (27 mg, 66% yield) of an orange oil: 58a 1H NMR (CDC13) 8 8.95 (m, 1H), 8.47 (m, 1H), 8.11 (m, 1H), 7.52 (br s, 1H), 7.31 (m, 1H), 7.26 (br s, 1H) 3.75 (s, 3H); 58b 1H NMR (CDCl3) 8 8.69 (m, 1H), 8.62 (m, 1H), 7.71 (m, 1H), 7.62 (br s, 1H), 7.39 (m, 1H), 7.19 (br s, 1H), 3.70 (s, 3H); LRMS (ESI) m/z calcd for CgHioNs [M + H] + 160, found 160; HRMS (ESI) m/z calcd forCgHsoN3 [M + H] + 160. 0875, found 160.0866 ; HPLC > 99% (tR = 19.80 min, 55 (A): 45 (B): 0.032 (C); tR = 9.47 min, 55 (A): 45 (B): 0.1 (C).
  • 11
  • [ 5460-29-7 ]
  • [ 51746-85-1 ]
  • [ 892860-06-9 ]
  • 12
  • [ 5292-43-3 ]
  • [ 51746-85-1 ]
  • [ 568629-89-0 ]
YieldReaction ConditionsOperation in experiment
With NaH; trifluoroacetic acid; In N-methyl-acetamide; dichloromethane; water; EXAMPLE 90 Preparation of 4-(3-pyridyl)imidazol-1-ylacetic Acid To a solution of 55 mg of 4-(3-pyridyl)imidazole (0.38 mmol, 1.0 eq.) in 2 ml of dry of dimethylformamide was added 15.5 mg of NaH (60%) (0.38 mmol, 1.0 eq.), and the mixture was stirred vigorously for 10 min. before dropwise addition of 0.05 ml of tert-butyl bromoacetate (0.34 mmol, 0.9 eq.). The resulting solution was heated at 70 C. for 30 min before it was diluted with 20 ml of water, and extracted with 3*30 ml of ethyl acetate. The organic extracts were combined and washed sequentially with water, and brine. The organic phase was dried with MgSO4, filtered, and evaporated to give 60 mg of a slight yellow solid. To a solution of above solid in 5 ml of CH2Cl2 was added 5 ml of trifluoroacetic acid, and the resulting solution was stirred at room temperature for 3 h. The solvent was then evaporated under vacuum to give 35 mg of final productproduct.
  • 13
  • [ 51746-85-1 ]
  • [ 325478-13-5 ]
  • 14
  • [ 51746-85-1 ]
  • C45H68N6O12 [ No CAS ]
  • 15
  • [ 51746-85-1 ]
  • C44H66N6O12 [ No CAS ]
  • 16
  • [ 51746-85-1 ]
  • [ 892860-49-0 ]
  • 17
  • [ 626-55-1 ]
  • K4[Fe(CN)6] [ No CAS ]
  • [ 51746-85-1 ]
  • 18
  • [ 51746-85-1 ]
  • [ 401522-23-4 ]
  • 19
  • [ 51746-85-1 ]
  • [ 401522-21-2 ]
  • 20
  • [ 51746-85-1 ]
  • [ 401522-22-3 ]
  • 21
  • [ 51746-85-1 ]
  • 9-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-15-ethyl-8-methoxy-4,6,8,10,12,15a-hexamethyl-3-[2-(4-pyridin-3-yl-imidazol-1-yl)-ethylsulfanyl]-octahydro-1,14-dioxa-cyclopentacyclotetradecene-2,5,11,13-tetraone [ No CAS ]
  • 22
  • [ 51746-85-1 ]
  • C44H66N4O11S [ No CAS ]
  • 23
  • [ 51746-85-1 ]
  • C44H64N4O11S [ No CAS ]
  • 24
  • [ 51746-85-1 ]
  • C60H86N4O16S [ No CAS ]
  • 25
  • [ 51746-85-1 ]
  • [ 401522-24-5 ]
  • 26
  • [ 51746-85-1 ]
  • [ 191114-48-4 ]
  • 28
  • [ 857797-77-4 ]
  • [ 51746-85-1 ]
  • 29
  • [ 857812-29-4 ]
  • [ 51746-85-1 ]
  • 30
  • [ 107-86-8 ]
  • [ 51746-85-1 ]
  • [ 261765-52-0 ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In tetrahydrofuran; for 24h;Heating / reflux; To a solution of 4-pyridin-3-yl-imidazole (1 g) in THF (34 ML) was added acetic acid (1.6 ML) and 3-methyl-2-butenal (3.3 ML) and the resulting solution was heated under gentle reflux for 24 hours. THF was then removed in vacuo and the residue was purified on a Flash 75 long column eluding with MeOH-CH2Cl2 to give the title compound as slightly yellow oil. MS: m/z 230 (M+H).
With acetic acid; In tetrahydrofuran; EXAMPLE 15 3,3-Dimethyl-3(4-Pyridin-3-yl-imidazol-1-yl)-propioaldehyde To a solution of 4-pyridin-3-yl-imidazole (1 g) in THF (34 mL) was added acetic acid (1.6 mL) and 3-methyl-2-butenal (3.3 mL) and the resulting solution was heated under gentle reflux for 24 hours. THF was then removed in vacuo and the residue was purified on a Flash 75 (silica gel column made by Biotage Division of Dyax Corp, U.S.) long column eluding with MeOH-CH2Cl2 to give the title compound as slightly yellow oil. MS: m/z 230 (M+H).
With acetic acid; In tetrahydrofuran; Example 15 3,3-Dimethyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propioaldehyde To a solution of 4-pyridin-3-yl-imidazole (1 g) in THF (34 mL) was added acetic acid (1.6 mL) and 3-methyl-2-butenal (3.3 mL) and the resulting solution was heated under gentle reflux for 24 hours. THF was then removed in vacuoand the residue was purified on a Flash 75 long column eluding with MeOH-CH2Cl2to give the title compound as slightly yellow oil. MS: m/z 230 (M+H).
  • 31
  • [ 78-85-3 ]
  • [ 51746-85-1 ]
  • [ 271795-48-3 ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In tetrahydrofuran; for 48h;Heating / reflux; 2-Methyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propioaldehyde To a solution of 4-pyridin-3-yl-imidazole (8.5 g) in THF (tetrahydrofuran) (293 ML) was added acetic acid (16.8 ML) and methacrolein (9.7 ML) and the resulting solution was heated under gentle reflux for 24 hours.. Another 9.7 ML methacrolein was added and the solution was heated under reflux for another 24 hours. THF was then removed in vacuo and the residue was purified on a Flash 75 long column eluding with MeOH-CH2Cl2 to give the title compound as slightly yellow oil. MS: m/z 215 (M+H).
With acetic acid; In tetrahydrofuran; Example 14 2-Methyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propioaldehyde To a solution of 4-pyridin-3-yl-imidazole (8.5 g) in THF (tetrahydrofuran) (293 mL) was added acetic acid (16.8 mL) and methacrolein (9.7 mL) and the resulting solution was heated under gentle reflux for 24 hours. Another 9.7 mL methacrolein was added and the solution was heated under reflux for another 24 hours. THF was then removed in vacuo and the residue was purified on a Flash 75 long column eluding with MeOH-CH2Cl2to give the title compound as slightly yellow oil. MS: m/z 215 (M+H).
With acetic acid; In tetrahydrofuran; Example 21 2-Methyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propioaldehyde To a solution of 4-pyridin-3-yl-imidazole (8.5 g) in THF (293 mL) was added acetic acid (16.8 mL) and methacrolein (9.7 mL) and the resulting solution was heated under gentle reflux for 24 hours. Another 9.7 mL methacrolein was added and the solution was heated under reflux for another 24 hours. THF was then removed in vacuoand the residue was purified on a Flash 75 long column eluding with MeOH-CH2Cl2to give the title compound as slightly yellow oil. MS: m/z 215 (M+H).
  • 32
  • [ 3492-41-9 ]
  • [ 51746-85-1 ]
  • [ 271795-49-4 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In dimethyl sulfoxide; at 70℃; for 48h; To a solution of 4-pyridin-3-yl-imidazole (50 mg) in DMSO (methyl sulfoxide) (1.7 ML) was added powered KOH (57 mg) and 3-bromo-2,2-dimethylpropyl acetate and the resulting suspension was heated at 70 C. for 48 hours.. water was added followed by CHCl3, the aqueous layer was extracted with CHCl3, the combined organic layers were washed with brine, dired over Na2SO4 and evaporated in vacuo.. The redisue was purified by preparative TLC (10% MeOH-90% CH2Cl2) the title compound as slightly yellow oil. MS: m/z 274 (M+H).
  • 33
  • C2H2O4*C8H7N3 [ No CAS ]
  • [ 51746-85-1 ]
  • 34
  • [ 254430-69-8 ]
  • [ 77287-34-4 ]
  • [ 51746-85-1 ]
YieldReaction ConditionsOperation in experiment
51% at 20 - 80℃; for 21h; Stage A2: 4-(3-pyridinyl)-1Himidazole 7.2 g of beta,beta-dimethoxy-3-pyridineethanamine in 15 ml of formamide is heated for 5 hours at 80 C. under nitrogen.. The reaction mixture is maintained under agitation at 20 C. for 16 hours.. In this way the sought product is obtained. (Yield=51%). NMR CDCl3 ppm3.24(s) 3.26(s) 6H 2 CH3O3.55(d, s after exch.) CH2-NHCO3.75(d, s after exch.) CH2-NHCO5.80(m) mobile H
  • 35
  • [ 51746-85-1 ]
  • [ 109-64-8 ]
  • 3-[1-(3-bromopropyl)-1H-imidazol-4-yl]-pyridine [ No CAS ]
 

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