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[ CAS No. 57667-50-2 ] {[proInfo.proName]}

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Chemical Structure| 57667-50-2
Chemical Structure| 57667-50-2
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Product Details of [ 57667-50-2 ]

CAS No. :57667-50-2 MDL No. :MFCD00964693
Formula : C10H13N3 Boiling Point : -
Linear Structure Formula :- InChI Key :MGKUHRRJQCKXOW-UHFFFAOYSA-N
M.W :175.23 Pubchem ID :799602
Synonyms :

Safety of [ 57667-50-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 57667-50-2 ]

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

  • Upstream synthesis route of [ 57667-50-2 ]
  • Downstream synthetic route of [ 57667-50-2 ]

[ 57667-50-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 934-32-7 ]
  • [ 106-94-5 ]
  • [ 57667-50-2 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: With potassium hydroxide In tetrahydrofuran; ethanol at 20℃; for 0.333333 h; Inert atmosphere
Stage #2: at 65℃; for 72 h; Inert atmosphere
lH-Benzimidazol-2-amine (3.9 g, 22.5 mmol) was dissolved in THF (30 mL) and ethanol(15 mL) in a sealed flask followed by addition of finely ground KOH (1.52 g, 27.0 mmol). The mixture was stirred at room temperature for 20 min., and then 1 -bromopropane (2.77 g, 22.53 mmol) added. The reaction mixture was heated to 65° C for 72 h, and then allowed to cool to room temperature. The reaction mixture was filtered, and the filtrate concentrated in vacuo. The crude residue was purified by silica gel chromatography (eluent: 1percent NH4OH/9percent MeOH/90percent CHCl3) to afford the product as a yellow solid (2.5 g, 63percent). LC-MS (ES) m/z = 176.0 (M + H)+ 1H NMR (400 MHz, DMSO-d6) 57.14 (s, IH), 7.10 (d, J = 8.0 Hz, IH), 6.86-6.92 (m, 2H), 6.38 (s, 2H), 3.90 (t, J = 6.9 Hz, 2H), 1.62-1.68 (m, 2H), 0.84 (t, J = 7.3 Hz, 3H).
Reference: [1] Patent: WO2010/126922, 2010, A1, . Location in patent: Page/Page column 15
  • 2
  • [ 100-51-6 ]
  • [ 57667-50-2 ]
YieldReaction ConditionsOperation in experiment
98% at 100℃; for 24 h; Amide-containing compounds with (benz)imidazol-2-yl groups can undergo catalytic directed cleavage with an alcohol nucleophile 11 in the presence of a metal catalyst. The following examples as depicted in Example Scheme ES can be listed.:_Using 9.30 molpercent Zn(OAc)2.17H20, 1.0 equiv 9b, 4.67 equiv lib, tBuOAc, 100 °C, 24 h Benzyl (1-propyl-1H-benzo[d]imidazol-2-yl)carbamate (21f) was obtained in 98percent (0.140 g, 0.46mmol) yield. Colorless oil. 13C-NMR (100 MHz, CDCI3): : 163.8, 154.3, 137.3, 129.8, 128.2,128.1, 127.9, 127.5, 122.5, 122.4, 110.5, 108.9, 66.9, 43.2, 21.4, 11.0. Also 1-propyl-1H- benzo[d]imidazol-2-amine (20e) was obtained in 69percent (60.0 mg, 0.34 mmol) yield. White crystals; m.p. 133 °C. 13C-NMR (100 MHz, DMSO-d6): : 155.4, 143.3, 134.8, 120.6, 118.3, 115.1, 107.9,43.3,22.2,11.4.
Reference: [1] Patent: WO2017/46133, 2017, A1, . Location in patent: Page/Page column 58; 59; 60
  • 3
  • [ 934-32-7 ]
  • [ 107-08-4 ]
  • [ 57667-50-2 ]
YieldReaction ConditionsOperation in experiment
61% With potassium carbonate; potassium hydroxide In acetone for 3 h; Reflux General procedure: #10;A mixture of 2-aminobenzimidazole 7 (1.33 g, 10.0 mmol), 10.0 mmol of the proper alkyl halide, 1.0 g of finely powdered KOH mixed with 2.0 g of anhydrous K2CO3 and acetone (50 mL) was heated at reflux for 3 h, with stirring. The solvent was removed in vacuo and the residue was partitioned between water (100 mL) and CH2Cl2 (100 mL), and the aqueous phase was further extracted twice with CH2Cl2. The combined extracts, dried over anhydrous Na2SO4, after removal of solvent afforded an oily or solid residue which was treated with a small amount of ethyl ether to give compounds 8a–e,l–o as whitish solids which were crystallized from the proper solvent. Only in the case of compound 8f, a preliminary purification by column chromatography [SiO2/ethyl acetate-acetone (1:1)] was necessary to obtain a crystalline compound.
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 62, p. 564 - 578
  • 4
  • [ 100-51-6 ]
  • [ 3459-92-5 ]
  • [ 57667-50-2 ]
YieldReaction ConditionsOperation in experiment
60% at 100℃; for 24 h; Amide-containing compounds with (benz)imidazol-2-yl groups can undergo catalytic directed cleavage with an alcohol nucleophile 11 in the presence of a metal catalyst. The following examples as depicted in Example Scheme ES can be listed.:_Using 10.0 molpercent anhydrous Zn(OAc)2, 1.0 equiv of ACDG-NH-CO-NH-ACDG 19a, 5.0 equiv anhydrous lib, anhydrous tBuOAc, 100 °C, 24 h; R = 1-propyl-1H-benzo[d]imidazol-2-yl, R3 = NHR1Benzyl (l-propyl-IH-benzo[d]imidazol-2-yl)carbamate (21f) was obtained in 60percent (0.093 g, 0.30mmol) yield. Dibenzyl carbonate (14a) was obtained in 21percent (0.025 g, 0.10 mmol) yield. Also 1-propyl-1H-benzo[d]imidazol-2-amine (20e) was obtained in 66percent (0.058 g, 0.33 mmol) yield.
Reference: [1] Patent: WO2017/46133, 2017, A1, . Location in patent: Page/Page column 58; 59; 60
  • 5
  • [ 506-68-3 ]
  • [ 55899-42-8 ]
  • [ 57667-50-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 7, p. 2414 - 2419
  • 6
  • [ 300707-15-7 ]
  • [ 57667-50-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 18, p. 6291 - 6297
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 8, p. 3362 - 3367
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