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Product Details of [ 98870-64-5 ]

CAS No. :98870-64-5 MDL No. :MFCD12545830
Formula : C10H17N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :AZYDWKHQWJEWGN-UHFFFAOYSA-N
M.W : 211.26 Pubchem ID :402562
Synonyms :

Safety of [ 98870-64-5 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 98870-64-5 ]

* 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 [ 98870-64-5 ]

[ 98870-64-5 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 127119-12-4 ]
  • [ 98870-64-5 ]
YieldReaction ConditionsOperation in experiment
94% With silica gel In dichloromethane at 50℃; for 10h;
82% With zinc dibromide In dichloromethane for 4h; Ambient temperature;
43% With water for 1h; Reflux;
40% With methanol; triethylamine at 20℃; for 96h; To 4-(2-tert-Butoxycarbonylamino-ethyl)-imidazole-1-carboxylic acid tert-butyl ester, were added 100 mL of methanol and 800 mL (5.73 mol) of triethylamine. The reaction mixture was allowed to stir at room temperature for four days and concentrated to oil. To the residue were added 40 mL of ether and 80 mL of hexane. This mixture was allowed to stand at room temperature resulting in precipitation of product, as a white solid, which were collected. The yield was 1.7g (8.0 mmol, 40%) (LC/MS M+H 212.1).
19% With potassium carbonate In methanol Heating; regioselective reaction;

  • 2
  • C20H33N3O6 [ No CAS ]
  • [ 98870-64-5 ]
YieldReaction ConditionsOperation in experiment
93% With silica gel In dichloromethane at 50℃; for 15h;
  • 3
  • [ 98870-64-5 ]
  • [ 205585-52-0 ]
  • tert-butyl 2-(2,5-dichloro-1H-imidazol-4-yl)ethylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 76% 2: 10% With N-chloro-succinimide In acetonitrile for 24h; Ambient temperature;
1: 40% 2: 49% With N-chloro-succinimide In acetonitrile
1: 49% 2: 40% With N-chloro-succinimide In acetonitrile at 20℃; for 20h; Inert atmosphere; Darkness; 3 4.1.1.
General protocol for the halogenation step General procedure: The N-Boc protected L-histamine, or the N-Boc protected L-histidinemethyl ester, or the N-Boc-protected L-carnosine methyl ester (1 mmol, 1 equiv) was dissolved in 20 mL of acetonitrile. Under argon atmosphere, 170 mg (1.3 mmol, 1.3 equiv) of N-halosuccinimide in 10 mL of acetonitrile were added dropwise. The mixture was stirred in the dark for 20 h at room temperature, then concentrated under vacuum. The residue was diluted with ethylacetate (30 mL) and washed with 20 mL of a saturated solution of sodium sulfite, then twice with 20 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography (eluent: CH2Cl2/CH3OH 95:5) to give the pure mono- and dihalogenated compounds. 4.1.3 tert-Butyl 2-(5-chloro-1H-imidazol-4-yl)ethylcarbamate (1a) Yield: 49%; Rf: 0.18 (DCM 9.5/MeOH 0.5); 1H NMR (400 MHz, DMSO): δ ppm 7.58 (s, 1H), 6.90 (t, J = 5.5 Hz, 1H), 3.14-3.05 (m, 2H), 2.63 (t, J = 7.3 Hz, 2H), 1.36 (s, 9H). 13C NMR (101 MHz, DMSO): δ ppm 155.47, 133.21, 122.65, 77.60, 39.15, 28.22, 24.11; MS ESI+/ESI-: m/z 246.31-248.30 (M+H)+, 244.31-246.30 (M-H)-. Anal. Calcd for C10H16ClN3O2: C, 48.88; H, 6.56; N, 17.10. Found: C, 48.82; H, 6.62; N, 17.01. 4.1.6 tert-Butyl 2-(2,5-dichloro-1H-imidazol-4-yl)ethylcarbamate (1d) Yield: 40%; Rf: 0.34 (DCM 9.5/MeOH 0.5); 1H NMR (400 MHz, DMSO): δ ppm 7.95 (s, 1H), 6.92 (t, J = 5.8 Hz, 1H), 3.12-3.05 (m, 2H), 2.58 (t, J = 7.1 Hz, 2H), 1.35 (s, 9H); 13C NMR (101 MHz, DMSO): δ ppm 155.53, 126.59, 77.70, 38.89, 28.26, 24.35; MS ESI+/ESI-: m/z 280.3-282.29 (M+H)+, 302.27-304.27 (M+Na)+, 278.17-280.16 (M-H)-. Anal. Calcd for C10H15Cl2N3O2: C, 42.87; H, 5.40; N, 15.00. Found: C, 42.85; H, 5.38; N, 15.03.
  • 4
  • [ 98870-64-5 ]
  • [ 205585-53-1 ]
  • tert-butyl 2-(2,5-dibromo-1H-imidazol-4-yl)ethylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 70% 2: 18% With N-Bromosuccinimide In acetonitrile for 24h; Ambient temperature;
1: 37% 2: 50% With N-Bromosuccinimide In acetonitrile
1: 50% 2: 37% With N-Bromosuccinimide In acetonitrile at 20℃; for 20h; Inert atmosphere; Darkness; 4 4.1.1.
General protocol for the halogenation step General procedure: The N-Boc protected L-histamine, or the N-Boc protected L-histidinemethyl ester, or the N-Boc-protected L-carnosine methyl ester (1 mmol, 1 equiv) was dissolved in 20 mL of acetonitrile. Under argon atmosphere, 170 mg (1.3 mmol, 1.3 equiv) of N-halosuccinimide in 10 mL of acetonitrile were added dropwise. The mixture was stirred in the dark for 20 h at room temperature, then concentrated under vacuum. The residue was diluted with ethylacetate (30 mL) and washed with 20 mL of a saturated solution of sodium sulfite, then twice with 20 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography (eluent: CH2Cl2/CH3OH 95:5) to give the pure mono- and dihalogenated compounds. 4.1.4 tert-Butyl 2-(5-bromo-1H-imidazol-4-yl)ethylcarbamate (1b) Yield: 50%; Rf: 0.16 (DCM 9.5/MeOH 0.5); mp: 53-55 °C; 1H NMR (400 MHz, DMSO): δ ppm 12.32 (s, 1H), 7.55 (s, 1H), 6.92 (t, J = 5.6 Hz, 1H), 3.14-2.98 (m, 2H), 2.61 (t, J = 7.4 Hz, 2H), 1.37 (s, 9H); 13C NMR (101 MHz, DMSO): δ ppm 155.49, 134.73, 77.63, 38.88, 28.27, 24.82; MS ESI+/ESI-: m/z 290.25-292.24 (M+H)+, 312.18-313.29 (M+Na)+, 289.33-290.32 (M-H)-. Anal. Calcd for C10H16BrN3O2: C, 41.39; H, 5.56; N, 14.48. Found: C, 41.43; H, 5.65; N, 14.41. 4.1.7 tert-Butyl 2-(2,5-dibromo-1H-imidazol-4-yl)ethylcarbamate (1e) Yield: 37%; Rf: 0.38 (DCM 9.5/MeOH 0.5); mp: 100-102 °C; 1H NMR (400 MHz, DMSO): δ ppm 11.06 (s, 1H), 6.92 (t, J = 5.6 Hz, 1H), 3.09 (dd, J = 13.2 Hz, J = 5.8 Hz, 2H), 2.58 (t, J = 13.3 Hz, 2H), 1.36 (s, 9H); 13C NMR (101 MHz, DMSO): δ ppm 155.47, 77.62, 38.96, 28.25, 25.04; MS ESI+/ESI-: m/z 389.42-391.38-393.35 (M+Na)+, 366.12-368.10-370.07 (M-H)-. Anal. Calcd for C10H15Br2N3O2: C, 32.54; H, 4.10; N, 11.39. Found: C, 32.56; H, 4.06; N, 11.43.
  • 5
  • [ 98870-64-5 ]
  • tert-butyl 2-(5-iodo-1H-imidazol-4-yl)ethylcarbamate [ No CAS ]
  • tert-butyl 2-(2,5-diiodo-1H-imidazol-4-yl)ethylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 71% 2: 25% With N-iodo-succinimide In acetonitrile for 24h; Ambient temperature;
1: 35% 2: 38% With N-iodo-succinimide In acetonitrile
1: 38% 2: 35% With N-iodo-succinimide In acetonitrile at 20℃; for 20h; Inert atmosphere; Darkness; 5 4.1.1.
General protocol for the halogenation step General procedure: The N-Boc protected L-histamine, or the N-Boc protected L-histidinemethyl ester, or the N-Boc-protected L-carnosine methyl ester (1 mmol, 1 equiv) was dissolved in 20 mL of acetonitrile. Under argon atmosphere, 170 mg (1.3 mmol, 1.3 equiv) of N-halosuccinimide in 10 mL of acetonitrile were added dropwise. The mixture was stirred in the dark for 20 h at room temperature, then concentrated under vacuum. The residue was diluted with ethylacetate (30 mL) and washed with 20 mL of a saturated solution of sodium sulfite, then twice with 20 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography (eluent: CH2Cl2/CH3OH 95:5) to give the pure mono- and dihalogenated compounds. 4.1.5 tert-Butyl 2-(5-iodo-1H-imidazol-4-yl)ethylcarbamate (1c) Yield: 38%; Rf: 0.26 (DCM 9.5/MeOH 0.5); mp: 55-57 °C; 1H NMR (400 MHz, DMSO): δ ppm 12.27 (s, 1H), 7.58 (s, 1H), 6.92 (t, J = 5.5 Hz, 1H), 3.11-3.05 (m, 2H), 2.60 (t, J = 7.4 Hz, 2H), 1.37 (s, 9H); 13C NMR (101 MHz, DMSO): δ ppm 155.37, 130.19, 77.62, 40.01, 28.30, 25.96; MS ESI+/ESI-: m/z 338.36 (M+H)+, 336.34 (M-H)-. Anal. Calcd for C10H16IN3O2: C, 35.62; H, 4.78; N, 12.46. Found: C, 35.58; H, 4.82; N, 12.43. 4.1.8 tert-Butyl 2-(2,5-diiodo-1H-imidazol-4-yl)ethylcarbamate (1f) Yield: 35%; Rf: 0.48 (DCM 9.5/MeOH 0.5); mp: 68-70 °C; 1H NMR (400 MHz, DMSO): δ ppm 12.76 (s, 1H), 6.90 (t, J = 5.6 Hz, 1H), 3.04-3.09 (m, 2H), 2.58 (t, J = 7.1 Hz, 2H), 1.37 (s, 9H); 13C NMR (101 MHz, DMSO): δ ppm 155.44, 136.18, 77.60, 40.15, 28.23, 26.04; MS ESI+/ESI-: m/z 464.12 (M+H)+, 486.12 (M+Na)+, 462.20 (M-H)-. Anal. Calcd for C10H15I2N3O2: C, 25.94; H, 3.27; N, 9.07. Found: C, 25.95; H, 3.28; N, 9.03.
  • 6
  • [ 6328-74-1 ]
  • [ 123-11-5 ]
  • [ 98870-64-5 ]
  • resin-bound isonitrile [ No CAS ]
  • [2-(1H-Imidazol-4-yl)-ethyl]-[2-(4-phenoxy-phenyl)-acetyl]-amino}-(4-methoxy-phenyl)-acetic acid [ No CAS ]
  • 7
  • [ 98870-64-5 ]
  • [2-(5-Chloro-2-iodo-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / NCS / acetonitrile / 24 h / Ambient temperature 2: 87 percent / NIS / acetonitrile / 24 h / Ambient temperature
  • 8
  • [ 98870-64-5 ]
  • [2-(5-Bromo-2-iodo-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 70 percent / NBS / acetonitrile / 24 h / Ambient temperature 2: 65 percent / NIS / acetonitrile / 24 h / Ambient temperature
  • 9
  • [ 98870-64-5 ]
  • 2-(5-Chloro-1H-imidazol-4-yl)-ethylamine; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / NCS / acetonitrile / 24 h / Ambient temperature 2: 71 percent / HCl / H2O / 72 h / Ambient temperature
  • 10
  • [ 98870-64-5 ]
  • 2-(5-Iodo-1H-imidazol-4-yl)-ethylamine; compound with trifluoro-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 71 percent / NIS / acetonitrile / 24 h / Ambient temperature 2: 91 percent / ethyl acetate / 2 h / Ambient temperature
  • 11
  • [ 98870-64-5 ]
  • 2-(5-Bromo-1H-imidazol-4-yl)-ethylamine; compound with trifluoro-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 70 percent / NBS / acetonitrile / 24 h / Ambient temperature 2: 85 percent / ethyl acetate / 2 h / Ambient temperature
  • 12
  • [ 98-59-9 ]
  • [ 98870-64-5 ]
  • [ 780801-96-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0 - 20℃; for 48h; 166 EXAMPLE 166, COMPOUND 166: (3,5-Dimethyl-pyridin-2-ylmethyl)-[2-(1H-imidazol-4-yl)-ethyl]-isoquinolin-1-ylmethyl-amine: EXAMPLE 166 COMPOUND 166: (3,5-Dimethyl-pyridin-2-ylmethyl)-[2-(1H-imidazol-4-yl)-ethyl]-isoquinolin-1-ylmethyl-amine: To a solution of [2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (1.66 g, 7.87 mmol) (Nigam, S. C. et al. Synth. Commun. 1989, 19, 3139-42) and Et3N (1.8 mL, 12.9 mmol) in CH2Cl2 (25 mL) at 0° C. was added p-toluene sulfonyl chloride (1.83 g, 9.62 mmol) and the reaction stirred at room temperature for 2 d. The mixture was diluted with CH2Cl2 (30 mL) and saturated aqueous NaHCO3 (40 mL) and the aqueous layer extracted with CH2Cl2 (2*10 mL). The combined organic extracts were dried (Na2SO4), concentrated and purified by column chromatography on silica gel (CH2Cl2/MeOH, 98:2) to give the tosyl-protected imidazole (2.14 g, 74%) as a beige solid. Deprotection with TFA using General Procedure F gave 2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethylamine (1.13 g, 73%) as a brown oil. 1H NMR (CDCl3) δ 1.29 (br s, 2H), 2.44 (s, 3H), 2.64 (t, 2H, J=6 Hz), 2.96 (t, 2H, J=6 Hz), 7.05 (s, 1H), 7.36 (d, 2H, J=9 Hz), 7.82 (d, 2H, J=9 Hz), 7.94 (s, 1H).
  • 13
  • [ 79982-56-2 ]
  • [ 98870-64-5 ]
  • [ 848344-90-1 ]
YieldReaction ConditionsOperation in experiment
61% With triethylamine In ethanol at 80℃; for 120h; To a mixture of 300 mg (0.52 mmol) of bis (2,2'-bipyridyl) dichloro osmium and 268 mg (1.26 mmol) of histamine t-Boc was added 54 mL of ethanol followed by 1.6 mL (11.4 mmol) of triethylamine. The mixture was allowed to stir at 80°C for five days and concentrated. The residue was purified by preparative HPLC using a gradient run with water and acetonitrile containing 0.1 % trifluoroacetic acid to give 250 mg (0.32 mmol, 61%) of osmium dibipyridyl t-Boc Histamine (compound 4) as a brown powder (LC/MS M+H 749.1).
  • 14
  • [(N,N'-dimethyl-2,2'-biimidazole)2OsCl2]Cl [ No CAS ]
  • [ 98870-64-5 ]
  • [ 848345-08-4 ]
YieldReaction ConditionsOperation in experiment
20% With triethylamine In ethanol for 18h; Heating / reflux; To 50 mg (0.080 mmol) of osmium dibiimidazole dichloride (compound 47) was added 71 mg (0.33 mmol) of [2-(1H-Imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (compound 1), followed by 300 µL (2.14 mmol) of triethylamine and 10 mL of ethanol. The mixture was heated to reflux for 18 hours and concentrated. The residue was purified by preparative reverse phase HPLC to give 13 mg (0. 016 mmol, 20%) of osmium di-biimidazole hist-t-Boc (compound 48) as a dark brown powder LC/MS M+H 761.2.
  • 15
  • [ 24424-99-5 ]
  • [ 56-92-8 ]
  • [ 98870-64-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In methanol; acetonitrile; Petroleum ether; 2 A 4-(N-(tert-butyloxycarbonyl)-2-aminoethyl) imidazole (VI) 75 ml of acetonitrile, 1.84 g (10 mmol) of histamine dihydrochloride, and 7 ml (50 mmol) of triethylamine are mixed in a 100 ml round-bottomed flask, whereupon 6.56 g (30 mmol) of di-tert-butyl dicarbonate is added. The reaction mixture is stirred at room temperature for 19 hours and then filtered. The acetonitrile solution is evaporated, and the residue is washed with 50 ml of petroleum ether. Undissolved substance is treated with 2 * 100 ml of ether. The ether phases are pooled and evaporated. A crystalline product is obtained which is identified by NMR to be histamine having both its amino group and its ring, nitrogen acylated with tert-butyloxycarbonyl. The acyl group on the ring nitrogen is removed by treatment of the product with 400 mul of triethylamine in 50 ml of methanol for 3.5 days. The solution is evaporated to thus leave an oil, the latter then being dissolved in 20 ml of ether. 40 ml of petroleum ether is added to the ether solution; this results in precipitation of an oil which crystallizes on stirring. 1.13 g of product VI is obtained the structure of which is established by NMR analysis, the NMR spectrum (CDC13) being the following: 2H 7.58 s, 5H 6.82 s, _CONHC H 2_ 3.41, 4-CH2-imidazole 2.81 t, (CH3)3C 1.43 s.
  • 16
  • [ 116-14-3 ]
  • [ 98870-64-5 ]
  • [ 943522-61-0 ]
YieldReaction ConditionsOperation in experiment
63% In tetrahydrofuran at -78 - 90℃; for 8h; 12 EXAMPLE 12; Into a 50 ml autoclave was poured 21.2 g of N-(t-butoxycarbonyl)histamine (100 mmol, melting point of 83°C) which was an imidazole compound, and the inside of the autoclave was cooled to -78°C and evacuation and replacement of atmosphere in the autoclave with nitrogen gas were carried out three times. After the inside of a system was evacuated, tetrafluoroethylene (TFE) was introduced until the inside pressure of the system reached 0.1 MPa·G. Then the temperature of the reaction system was increased to 90°C, and TFE was further introduced to maintain the inside pressure of the reaction system at 0.3 to 0.5 MPa·G. Supply of TFE was stopped when the amount of TFE reached 1.1 equivalents (11 g = 110 mmol) to N-(t-butoxycarbonyl)histamine, and stirring was continued at 90°C. Eight hours after starting of the stirring, the inside of the reaction system was brought to room temperature, followed by evacuation, dissolution in chloroform and re-crystallization with hexane to obtain 17.6 g of a solid (yield: 63 %). According to a NMR analysis, it was confirmed that this product was N-(t-butoxycarbony)-N1-(1,1,2,2-tetrafluoroethyl)histamine. To this crude reaction product was added 2.84 g (20 mmol) of ethyl trifluoroacetate, and yield by a 19F-NMR analysis based on ethyl trifluoroacetate was 91 %. 19F-NMR (CD3COCD3): δ-100.4 (2F), -139.8 (2F) ppm 1H-NMR (CD3COCD3): δ1.31 (9H, s), 2.70 - 3.10 (4H, m), 6.80 (1H, s), 7.27 (1H, m), 7.54 (1H, s) ppm
  • 17
  • [ 98870-64-5 ]
  • [ 74-88-4 ]
  • [ 200941-95-3 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: Nα-(tert-butoxycarbonyl)histamine With sodium hydride In N,N-dimethyl-formamide at -15℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at -15 - -5℃; for 3h; Inert atmosphere; regiospecific reaction;
34% Stage #1: Nα-(tert-butoxycarbonyl)histamine With sodium hydride In tetrahydrofuran at -10℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at -10℃; for 2.5h; 192 EXAMPLE 192, COMPOUND 192: (3,5-dimethyl-pyridin-2-ylmethyl)-isoguinolin-1-ylmethyl-[2-(1-methyl-1H-imidazol-4-yl)-ethyl]-amine EXAMPLE 192 COMPOUND 192: (3,5-dimethyl-pyridin-2-ylmethyl)-isoguinolin-1-ylmethyl-[2-(1-methyl-1H-imidazol-4-yl)-ethyl]-amine To a solution of [2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (512 mg, 2.42 mmol) in THF (20 mL) at -10° C. was added NaH (60%, 97 mg, 2.42 mmol). After stirring at -10° C. for 30 min, MeI (0.14 mL, 2.17 mmol) was added. After stirring at -10° C. for 2.5 h, the reaction mixture was concentrated to afford a yellow oil. Purification by flash column chromatography on silica gel using 2% MeOH/CH2Cl2 afforded [2-(1-methyl-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester as a yellow oil (144 mg, 34%).
  • 18
  • [ 24424-99-5 ]
  • [ 98870-64-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine 2: potassium carbonate / methanol / Heating
  • 19
  • [ 98870-64-5 ]
  • [ 99221-76-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-chloro-succinimide / acetonitrile 2: trifluoroacetic acid / dichloromethane
Multi-step reaction with 2 steps 1: N-chloro-succinimide / acetonitrile / 20 h / 20 °C / Inert atmosphere; Darkness 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
  • 20
  • [ 98870-64-5 ]
  • [ 22004-17-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-iodo-succinimide / acetonitrile 2: trifluoroacetic acid / dichloromethane
Multi-step reaction with 2 steps 1: N-iodo-succinimide / acetonitrile / 20 h / 20 °C / Inert atmosphere; Darkness 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
  • 21
  • [ 98870-64-5 ]
  • 2-(5-bromo-1H-imidazol-4-yl)ethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / acetonitrile 2: trifluoroacetic acid / dichloromethane
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / acetonitrile / 20 h / 20 °C / Inert atmosphere; Darkness 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
  • 22
  • [ 98870-64-5 ]
  • 2-(2,5-dichloro-1H-imidazol-4-yl)ethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-chloro-succinimide / acetonitrile 2: trifluoroacetic acid / dichloromethane
Multi-step reaction with 2 steps 1: N-chloro-succinimide / acetonitrile / 20 h / 20 °C / Inert atmosphere; Darkness 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
  • 23
  • [ 98870-64-5 ]
  • 2-(2,5-dibromo-1H-imidazol-4-yl)ethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / acetonitrile 2: trifluoroacetic acid / dichloromethane
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / acetonitrile / 20 h / 20 °C / Inert atmosphere; Darkness 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
  • 24
  • [ 100-39-0 ]
  • [ 98870-64-5 ]
  • [ 1373501-26-8 ]
YieldReaction ConditionsOperation in experiment
38% With potassium carbonate In acetone at 60 - 70℃;
  • 25
  • [ 100-39-0 ]
  • [ 98870-64-5 ]
  • [ 1373501-27-9 ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: Nα-(tert-butoxycarbonyl)histamine With sodium hydride In N,N-dimethyl-formamide at -15℃; for 1h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at -15 - -5℃; for 3h; Inert atmosphere; regiospecific reaction;
  • 26
  • [ 75-03-6 ]
  • [ 98870-64-5 ]
  • [ 1023299-75-3 ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: Nα-(tert-butoxycarbonyl)histamine With sodium hydride In N,N-dimethyl-formamide at -15℃; for 1h; Inert atmosphere; Stage #2: ethyl iodide In N,N-dimethyl-formamide at -15 - -5℃; for 3h; Inert atmosphere; regiospecific reaction;
  • 27
  • [ 75-03-6 ]
  • [ 98870-64-5 ]
  • [ 1373501-25-7 ]
YieldReaction ConditionsOperation in experiment
47% With potassium carbonate In acetone at 60 - 70℃;
  • 28
  • [ 98870-64-5 ]
  • [ 1373501-28-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -15 °C / Inert atmosphere 1.2: 3 h / -15 - -5 °C / Inert atmosphere 2.1: 85 - 90 °C / Neat (no solvent)
  • 29
  • [ 98870-64-5 ]
  • [ 1373501-29-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -15 °C / Inert atmosphere 1.2: 3 h / -15 - -5 °C / Inert atmosphere 2.1: 85 - 90 °C / Neat (no solvent)
  • 30
  • [ 98870-64-5 ]
  • [ 74-88-4 ]
  • [ 1373501-24-6 ]
YieldReaction ConditionsOperation in experiment
87% With potassium carbonate In acetone at 60 - 70℃;
  • 31
  • [ 98870-64-5 ]
  • [ 22004-37-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-iodo-succinimide / acetonitrile / 20 h / 20 °C / Inert atmosphere; Darkness 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
  • 32
  • C34H33BrO8 [ No CAS ]
  • [ 98870-64-5 ]
  • C44H49N3O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With N-ethyl-N,N-diisopropylamine; potassium iodide In acetonitrile for 24h; Reflux;
  • 33
  • (Z)-2-(2-((R)-(3,4-bis((4-methoxybenzyl)oxy)phenyl)bromomethyl)benzo[d] [1,3]dioxol-5-yl)vinyl(2,2,2-trifluoroethyl) sulfate [ No CAS ]
  • [ 98870-64-5 ]
  • (Z)-2-(2-((S)-(3,4-bis((4-methoxybenzyl)oxy)phenyl)(4-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-imidazol-1-yl)methyl)benzo[d][1,3]dioxol-5-yl)vinyl (2,2,2-trifluoroethyl) sulfate [ No CAS ]
  • (Z)-2-(2-((S)-(3,4-bis((4-methoxybenzyl)oxy)phenyl)(5-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-imidazol-1-yl)methyl)benzo[d][1,3]dioxol-5-yl)vinyl (2,2,2-trifluoroethyl) sulfate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 40℃; for 60h; Inert atmosphere; Overall yield = 36 %; Overall yield = 11 mg;
  • 34
  • [ 98870-64-5 ]
  • N-(2-(1-((benzyloxy)methyl)-5-bromo-1H-imidazol-4-yl)ethyl)cinnamamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere
  • 35
  • [ 98870-64-5 ]
  • N-(2-(1-((benzyloxy)methyl)-5-bromo-1H-imidazol-4-yl)ethyl)-N-(4-(tert-butyl)benzyl)cinnamamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere
  • 36
  • [ 98870-64-5 ]
  • (E)-N-benzyl-N-(2-(1-((benzyloxy)methyl)-5-bromo-1H-imidazol-4-yl)ethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere
  • 37
  • [ 98870-64-5 ]
  • (E)-N-benzyl-N-(2-(1-((benzyloxy)methyl)-5-bromo-1H-imidazol-4-yl)ethyl)-3-(pyridin-4-yl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere
  • 38
  • [ 98870-64-5 ]
  • (E)-N-benzyl-N-(2-(1-((benzyloxy)methyl)-5-bromo-1H-imidazol-4-yl)ethyl)-3-(4-(trifluoromethyl)phenyl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere
  • 39
  • [ 98870-64-5 ]
  • N-(2-(1-((benzyloxy)methyl)-5-bromo-1H-imidazol-4-yl)ethyl)-N-(naphthalen-2-ylmethyl)cinnamamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere
  • 40
  • [ 98870-64-5 ]
  • (Z)-4-benzylidene-3-((benzyloxy)methyl)-6-(4-methylbenzyl)-4,6,7,8-tetrahydroimidazo[4,5-d]azepin-5(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere 6.1: N-Methyldicyclohexylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
  • 41
  • [ 98870-64-5 ]
  • (Z)-4-benzylidene-3-((benzyloxy)methyl)-6-(4-fluorobenzyl)-4,6,7,8-tetrahydroimidazo[4,5-d]azepin-5(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere 6.1: N-Methyldicyclohexylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
  • 42
  • [ 98870-64-5 ]
  • (Z)-4-benzylidene-3-((benzyloxy)methyl)-6-(3,5-dimethylbenzyl)-4,6,7,8-tetrahydroimidazo[4,5-d]azepin-5(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere 6.1: N-Methyldicyclohexylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
  • 43
  • [ 98870-64-5 ]
  • (Z)-4-benzylidene-3-((benzyloxy)methyl)-6-(3-methylbenzyl)-4,6,7,8-tetrahydroimidazo[4,5-d]azepin-5(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere 6.1: N-Methyldicyclohexylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
  • 44
  • [ 98870-64-5 ]
  • (Z)-6-([1,1'-biphenyl]-4-ylmethyl)-4-benzylidene-3-((benzyloxy)methyl)-4,6,7,8-tetrahydroimidazo[4,5-d]azepin-5(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere 6.1: N-Methyldicyclohexylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
  • 45
  • [ 98870-64-5 ]
  • N-(2-(1-((benzyloxy)methyl)-5-bromo-1H-imidazol-4-yl)ethyl)-N-(4-methylbenzyl)cinnamamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere
  • 46
  • [ 98870-64-5 ]
  • (Z)-4-benzylidene-3-((benzyloxy)methyl)-6-(4-chlorobenzyl)-4,6,7,8-tetrahydroimidazo[4,5-d]azepin-5(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere 6.1: N-Methyldicyclohexylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
  • 47
  • [ 98870-64-5 ]
  • (Z)-4-benzylidene-3-((benzyloxy)methyl)-6-(4-methoxybenzyl)-4,6,7,8-tetrahydroimidazo[4,5-d]azepin-5(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere 6.1: N-Methyldicyclohexylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
  • 48
  • [ 98870-64-5 ]
  • (Z)-4-benzylidene-3-((benzyloxy)methyl)-6-(2-methylbenzyl)-4,6,7,8-tetrahydroimidazo[4,5-d]azepin-5(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere 6.1: N-Methyldicyclohexylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
  • 49
  • [ 98870-64-5 ]
  • (Z)-4-benzylidene-3-((benzyloxy)methyl)-6-(4-(tert-butyl)benzyl)-4,6,7,8-tetrahydroimidazo[4,5-d]azepin-5(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere 6.1: N-Methyldicyclohexylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
  • 50
  • [ 98870-64-5 ]
  • (Z)-6-benzyl-3-((benzyloxy)methyl)-4-(3,4,5-trimethoxybenzylidene)-4,6,7,8-tetrahydroimidazo[4,5-d]azepin-5(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 30 h / 20 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 0 °C / Inert atmosphere 5.2: 8 h / 20 °C / Inert atmosphere 6.1: N-Methyldicyclohexylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 120 °C / Inert atmosphere
  • 51
  • [ 98870-64-5 ]
  • [ 205585-53-1 ]
YieldReaction ConditionsOperation in experiment
92% With N-Bromosuccinimide In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;
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