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[ CAS No. 95-14-7 ] {[proInfo.proName]}

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Product Details of [ 95-14-7 ]

CAS No. :95-14-7 MDL No. :MFCD00005699
Formula : C6H5N3 Boiling Point : -
Linear Structure Formula :- InChI Key :QRUDEWIWKLJBPS-UHFFFAOYSA-N
M.W : 119.12 Pubchem ID :7220
Synonyms :
Chemical Name :1H-Benzo[d][1,2,3]triazole

Calculated chemistry of [ 95-14-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.89
TPSA : 41.57 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) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.78
Log Po/w (XLOGP3) : 1.1
Log Po/w (WLOGP) : 0.96
Log Po/w (MLOGP) : 0.97
Log Po/w (SILICOS-IT) : 1.67
Consensus Log Po/w : 1.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.01
Solubility : 1.16 mg/ml ; 0.00974 mol/l
Class : Soluble
Log S (Ali) : -1.57
Solubility : 3.24 mg/ml ; 0.0272 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.387 mg/ml ; 0.00325 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 95-14-7 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P280-P301+P312-P305+P351+P338-P330-P337+P313-P403-P501 UN#:3077
Hazard Statements:H302-H318-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 95-14-7 ]

* 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 [ 95-14-7 ]
  • Downstream synthetic route of [ 95-14-7 ]

[ 95-14-7 ] Synthesis Path-Upstream   1~30

  • 1
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  • [ 19155-24-9 ]
Reference: [1] Heterocycles, 1994, vol. 37, # 3, p. 1913 - 1932
  • 2
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  • [ 106-95-6 ]
  • [ 52298-91-6 ]
  • [ 82813-00-1 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 1, p. 280 - 284
[2] Heterocycles, 1994, vol. 38, # 6, p. 1367 - 1374
[3] Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 11, p. 2133 - 2138
[4] Chemische Berichte, 1938, vol. 71, p. 596,602
[5] Liebigs Annalen der Chemie, 1992, # 8, p. 843 - 854
[6] Synthetic Communications, 1996, vol. 26, # 14, p. 2657 - 2670
[7] Heterocycles, 2004, vol. 63, # 5, p. 1077 - 1081
  • 3
  • [ 95-14-7 ]
  • [ 107-05-1 ]
  • [ 52298-91-6 ]
  • [ 82813-00-1 ]
Reference: [1] Synthetic Communications, 2010, vol. 40, # 17, p. 2525 - 2530
[2] Journal of Organometallic Chemistry, 2012, vol. 710, p. 1 - 5
  • 4
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  • [ 106-95-6 ]
  • [ 52298-91-6 ]
Reference: [1] Green Chemistry, 2009, vol. 11, # 8, p. 1115 - 1120
[2] J. Appl. Chem. USSR (Engl. Transl.), 1990, vol. 63, # 5, p. 1096 - 1098[3] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1990, vol. 63, # 5, p. 1194 - 1197
[4] Polish Journal of Chemistry, 1999, vol. 73, # 8, p. 1253 - 1258
[5] Journal of Structural Chemistry, 2005, vol. 46, # 1, p. 172 - 176
  • 5
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  • [ 106-96-7 ]
  • [ 52298-91-6 ]
  • [ 142321-23-1 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 32, p. 5641 - 5644
  • 6
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  • [ 107-18-6 ]
  • [ 52298-91-6 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 9, p. 1613 - 1621
  • 7
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  • [ 50-00-0 ]
  • [ 28539-02-8 ]
YieldReaction ConditionsOperation in experiment
94% at 25℃; for 0.0833333 h; Example 30 1-Hydroxymethyl-1H-benzotriazole [0464] Dissolve 10 g (83.94 mmol) of 1H-benzotriazole in 6.81 mL (83.94 mmol) of a 37percent aqueous solution of formaldehyde. Stir and bring the mixture to a temperature of 25° C. After 5 minutes, the reaction mixture solidifies. Cool the solution to ambient temperature. Filter and wash with diethyl ether. Triturate the residue in the cold in tetrahydrofuran and filter (Int. 94). [0465] Yield: 94percent [0466] Melting point: 148-150° C. (tetrahydrofuran and diethyl ether)
90% at 20℃; for 2 h; Weigh benzotriazole (5mmol, 596mg), 40percent formic acid (5mmol, 375mg) placed in 100mL round bottomBottles , 60mL of methanol was added , stirred for 2 hours at room temperature , there are a lot of white solid precipitated , suction filtered , the filter cake washed with cold methanol , and dried ,To give 1-hydroxymethyl benzene and triazole , quality 671mg ( 90percent yield ) . Weigh 1-hydroxymethyl benzo triazole (lmmol,149mg), 4_ (4_ morpholinyl ) aniline (lmmol, 178mg) a 50mL round bottom flask was added 20mL of methanol , stirred at room temperatureMixed 3h, has a large amount of solid precipitated , suction filtered , the filter cake washed with cold methanol , and dried to give the title compound . An off-white solid , mass :278mg ( 90percent yield ) .
35% at 80℃; for 1 h; (1) 11.9 g of benzotriazole,30ml water and30ml formaldehyde mixture,Heating to dissolve the solid,At 80 water bath heating 1h,Cool and filter to give white needles,Recrystallization from ethyl acetate gave white crystals,Namely hydroxymethyl benzotriazole;
Reference: [1] Patent: US2004/67998, 2004, A1, . Location in patent: Page/Page column 24
[2] Journal of the American Chemical Society, 2017, vol. 139, # 27, p. 9281 - 9290
[3] Patent: CN102688233, 2016, B, . Location in patent: Paragraph 0095; 0098
[4] Patent: CN106188103, 2016, A, . Location in patent: Paragraph 0035; 0037
[5] Journal of the American Chemical Society, 1952, vol. 74, p. 3868
[6] Justus Liebigs Annalen der Chemie, 1934, vol. 511, p. 213,240
[7] Recueil des Travaux Chimiques des Pays-Bas, 1988, vol. 107, # 11, p. 641 - 646
[8] Journal of Organic Chemistry, 1989, vol. 54, # 26, p. 6022 - 6029
[9] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 15, p. 2009 - 2014
[10] Organic Preparations and Procedures International, 1992, vol. 24, # 4, p. 475 - 478
[11] Tetrahedron Letters, 2006, vol. 47, # 50, p. 8981 - 8982
[12] Organic Letters, 2012, vol. 14, # 8, p. 2138 - 2141
[13] Patent: , 2016, , . Location in patent: Paragraph 0037
[14] Patent: CN108774252, 2018, A, . Location in patent: Paragraph 0032; 0034
  • 8
  • [ 95-14-7 ]
  • [ 50-00-0 ]
  • [ 28539-02-8 ]
  • [ 136969-48-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2, 1990, # 6, p. 921 - 924
[2] Journal of the Chemical Society, Perkin Transactions 2, 1990, # 6, p. 921 - 924
[3] Journal of the Chemical Society, Perkin Transactions 2, 1990, # 6, p. 921 - 924
  • 9
  • [ 95-14-7 ]
  • [ 591-50-4 ]
  • [ 883-39-6 ]
YieldReaction ConditionsOperation in experiment
50% With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24 h; Inert atmosphere General procedure: To a solution of Cu(OAc)2*H2O (0.01 mmol) in DMF (2 mL) were added aryl iodide (1.2 mmol), nitrogen-containing heterocycle (1.0 mmol), and Cs2CO3 (2 mmol) under nitrogen atmosphere. The mixture was stirred at 110 °C for 24 h. After cooling to ambient temperature, the mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel.
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 31, p. 5617 - 5620
[2] RSC Advances, 2015, vol. 5, # 51, p. 40628 - 40635
[3] Synthetic Communications, 2012, vol. 42, # 15, p. 2217 - 2228
[4] Journal of Organic Chemistry, 2004, vol. 69, # 17, p. 5578 - 5587
[5] Synthesis, 2012, vol. 44, # 7, p. 1063 - 1068
[6] Organic and Biomolecular Chemistry, 2014, vol. 12, # 9, p. 1475 - 1487
[7] Tetrahedron, 2011, vol. 67, # 29, p. 5282 - 5288
  • 10
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  • [ 108-86-1 ]
  • [ 883-39-6 ]
YieldReaction ConditionsOperation in experiment
70% With copper(II) ferrite; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 155℃; for 24 h; Inert atmosphere General procedure: To a solution of N-heterocycle (1 equiv), bromobenzene (1.02 equiv) and tBuOK (2 equiv) in dry DMF, CuFe2O4 (10 mol percent) was added and heated at reflux for 24 h under N2 atmosphere. After cooling to room temperature, the mixture was diluted with ethyl acetate and the catalyst was separated by a magnetic separator. The catalyst was washed with ethyl acetate. The combined ethyl acetate layer was washed with water (twice), dried over anhydrous Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel column chromatography using petroleum ether/ethyl acetate to yield N-arylated product.
Reference: [1] Chinese Journal of Chemistry, 2012, vol. 30, # 10, p. 2394 - 2400
[2] Journal of the American Chemical Society, 2007, vol. 129, # 45, p. 13879 - 13886
[3] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1924 - 1927
  • 11
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  • [ 883-39-6 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 31, p. 5621 - 5622
[2] Synlett, 2000, # 7, p. 1022 - 1024
  • 12
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  • [ 883-39-6 ]
YieldReaction ConditionsOperation in experiment
95% With potassium phosphate; CuI In <i>N</i>-methyl-acetamide 1 -Phenylbenzotriazole
Using the general procedure, benzotriazole (0.119 g, 1.00 mmol) was coupled with iodobenzene (134 μL, 1.20 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol percent), K3PO4 (2.1 mmol), trans-N,N'-dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol percent) and dimethylformamide (1.0 mL) to give the crude product.
Column chromatography (2*15 cm, hexane:ethyl acetate 9:1) provided 0.186 g (95percent yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ8.17 (m, 1H), 7.78 (m, 3H), 7.62 (m, 2H), 7.55 (m, 2H), 7.42 (m, 1H).
Reference: [1] Patent: US2003/65187, 2003, A1,
  • 13
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  • [ 88284-48-4 ]
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  • [ 1916-72-9 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 8, p. 3198 - 3209
  • 14
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  • [ 883-39-6 ]
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 47, p. 4465 - 4467
  • 15
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  • [ 883-39-6 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997, vol. 36, # 8, p. 700 - 702
  • 16
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  • [ 591-50-4 ]
  • [ 883-39-6 ]
  • [ 1916-72-9 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 12, p. 6408 - 6422
[2] Tetrahedron Letters, 1998, vol. 39, # 31, p. 5617 - 5620
[3] Tetrahedron Letters, 1998, vol. 39, # 31, p. 5617 - 5620
  • 17
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  • [ 591-50-4 ]
  • [ 429-41-4 ]
  • [ 16584-01-3 ]
  • [ 708-43-0 ]
  • [ 883-39-6 ]
Reference: [1] Synthesis, 2008, # 11, p. 1707 - 1716
  • 18
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  • [ 1916-72-9 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 31, p. 5621 - 5622
  • 19
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  • [ 6299-39-4 ]
YieldReaction ConditionsOperation in experiment
87% at 0 - 60℃; for 3.5 h; Benzotriazole (2 g, 16.8 mmol) was dissolved in concentrated sulfuric acid (70 mL) and cooled to 0° C. To this was added potassium nitrate (3.44 g, 34 mmol) in small portions over 30 min. Once this had been completed, the reaction mixture was heated to 60° C. for 3 h. After cooling, the reaction mixture was poured slowly onto ice. The resultant suspension was filtered to remove the precipitate and washed thoroughly with water until the washings were consistently of pH 7. After drying, 4(7)-nitrobenzotriazole was isolated as yellow powder, 2.39 g (87percent), m.p. 218° C.; 1H NMR (400 MHz, DMSO-d6) δ 7.65 (t, 1H), 8.47 (d, 1H), 8.61 (d, 1H).
73% at 20℃; To cool solution of 2.65 mL of nitric acid and 10 mL sulfuric acid was added drop wise in a solution of 5.37 g benzotriazole in 10 mL sulfuric acid. The reaction was kept at room temperature overnight. The reaction mixture was then over ice and yellow precipitates were formed which are filtered, washed with water, and dried. The purification was done by slurrying of nitrobenzotriazole in hot acetonitrile and product was filtered.
Reference: [1] Magnetic Resonance in Chemistry, 2009, vol. 47, # 2, p. 142 - 148
[2] Patent: US2012/130078, 2012, A1, . Location in patent: Page/Page column 5
[3] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5260 - 5267
[4] Journal of Organic Chemistry, 1992, vol. 57, # 1, p. 190 - 195
[5] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997, vol. 36, # 11, p. 1071 - 1073
[6] Justus Liebigs Annalen der Chemie, 1934, vol. 511, p. 213,240
[7] Patent: US4240822, 1980, A,
[8] Patent: US4086242, 1978, A,
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  • [ 6299-39-4 ]
  • [ 2338-12-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 17, p. 4791 - 4794
[2] Bulletin des Societes Chimiques Belges, 1984, vol. 93, # 11, p. 973 - 982
[3] Heterocycles, 2005, vol. 65, # 10, p. 2471 - 2481
  • 21
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  • [ 17374-26-4 ]
YieldReaction ConditionsOperation in experiment
68% at 60 - 80℃; for 49 h; General procedure: A slightly modification of the previously described procedure [39] was used. 1H-Benzimidazole (31, 3g) or 193 1H-benzotriazole (32, 3g) was dissolved in a mixture of 69percent 194 HNO3 (50mL) and 100percent HNO3 (3mL). Next, the solution was heated to a temperature of 80°C and 195 Br2 (6 equiv.) was added drop by drop within 1h. The reaction mixture was then vigorously stirred at 60°C for 48h, and after this time it was cooled to room temperature, the excess of unreacted Br2 was removed in the flow of 196 nitrogen and trapped in a 20percent aqueous solution of 197 Na2S2O5 (100mL). Next, the content of the flask was poured into mixture of ice-cold 15 H2O (200mL) and saturated aqueous solution of Na2S2O5 (10mL). The resulting orange precipitate was filtered off and washed with H2O (50mL) and EtOH (50mL). The resulting crude product was washed several times with hot MeOH (50mL) yielding 198 4,5,6,7-tetrabromo-1H-benzimidazole (TBBi, 33, 5.56g, 12.82mmol, 50percent) or 4,5,6,7-tetrabromo-1H-benzotriazole (TBBt, 34, 7.45g, 17.14mmol, 68percent) as white solids, respectively. The identity of both polybrominated products (33 and 34) was confirmed by high-resolution mass spectrometry (HRMS). The 1H, 13C NMR and melting point values were consistent with the literature data. For 48 TBBi 33: white solid; mp 339–340°C (MeOH) [339°C (no data)] [88]; HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C7H3Br4N2+ m/z: 434.6983, Found 434.7024; [2M+H]+ Calcd for C14H5Br8N4+ m/z: 868.3893, Found 868.4806. For TBBt 34: white solid; mp 264–266°C (MeOH) [262–266°C (acetic acid)] [89]; HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C9H7Br5N3+ m/z: 435.6941, Found 435.6629.
59% at 60 - 80℃; for 49 h; Inert atmosphere; Irradiation 1H-Benzotriazole 4 (6 g, 50.4 mmol) was dissolved in a mixture of 69percent HNO3 (150 mL) and fuming 100percent HNO3 (10 mL). Next, the solution was heated to a temperature of 80 °C and Br2 (48.3 g, 302 mmol, 15 mL) was added dropwise within 1 h. The reaction mixture was stirred vigorously using mechanical stirrer at 60 °C for 48 h and irradiated by exposure to UV light. Subsequently, content of the flask was cooled to room temperature, the excess of unreacted bromine was removed in the gentle flow of nitrogen and trapped into a 20percent solution of sodium pyrosulfite (150 mL). The suspension was poured into mixture of ice-cold H2O (300mL) and saturated Na2S2O5 (20mL). The resulting yellowish precipitate was filtered off, and washed with H2O (100mL) and EtOH (100mL), respectively. The obtained crude product was refluxed several times in the mixture of MeOH (50mL) and i-PrOH (25mL), and hot saturated solution was filtered off yielding white crystals 5 (13g, 29.9mmol, 59percent). The purity of the compound 5 was confirmed by high-resolution mass spectrometry (HRMS). The 1H, 13C NMR and m.p. were consistent with the literature data [46]. White solid; mp 264–266°C; Rf [CHCl3/MeOH (99:1, v/v)] 0.16; HRMS (ESI+, m/z): [M+H]+calcd=435.6941, [M+H]+found=435.6629.
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 307 - 333
[2] European Journal of Medicinal Chemistry, 2014, vol. 84, p. 364 - 374
[3] Journal of the American Chemical Society, 1957, vol. 79, p. 4395,4399
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1573 - 1578
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YieldReaction ConditionsOperation in experiment
27% at 20 - 50℃; To a solution of benzotriazole (5 g, 42.01 mmol) and potassium hydroxide (1 1 .76 g, 0.21 mol) in water (50 mL) was added hydroxylamine-O-sulfonic acid (9.49 g, 84.02 mmol) in several portions and the temperature of the reaction mixture was kept below 50°C. After the addition, the mixture was stirred at room temperature for 2 hours. The resulting precipitate was removed by filtration and washed thoroughly with EtOAc. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography using Petroleum Ether:EtOAc (300:1 ) as eluting solvents to afford 1 H-benzo[cfl[1 ,2,3]triazol-1-amine as a white solid (1.52 g, 27percent). MS (ESI) m/z: 135 [M+H]+.
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 15, p. 2343 - 2355
[2] Patent: WO2015/100609, 2015, A1, . Location in patent: Page/Page column 37
[3] Tetrahedron Letters, 1997, vol. 38, # 28, p. 5037 - 5040
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  • [ 6627-89-0 ]
  • [ 657-27-2 ]
  • [ 2418-95-3 ]
YieldReaction ConditionsOperation in experiment
~ 75 %Spectr. at 60℃; for 18 h; A solution of L-lysine monohydrochloride (20.0 g, 109.5 mmol) and benzotriazole (14.3 g, 120.0 mmol) in a mixture of water (66.6 mL) and THF (111.0 mL) at pH 12 was treated with t-butyl phenyl carbonate (24.3 mL, 131.4 mmol) and stirred 18 hours at 600C. The mixture, initially 2 layers, became a clear orange solution and the product was approximately 75percent (NMR) .
Reference: [1] Patent: WO2008/14811, 2008, A1, . Location in patent: Page/Page column 16
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  • [ 621-84-1 ]
  • [ 298-12-4 ]
  • [ 124676-19-3 ]
YieldReaction ConditionsOperation in experiment
87% at 120℃; for 2 h; To a 250 ml. flask equipped mechanical stirring, was added 2-oxoacetic acid hydrate (9.2 g,0.1 mol), benzyl carbamate (15.1 g, 0.1 mol) and 1H-benzo[dj[1,2,3jtriazole (9.2 g, 0.1 mol), and toluene (300 mL). The resulting solution was stirred for 2 h at 120 °C in an oil bath. The resulting mixture was filtered and the solid residue was washed with petroleum ether (3x), and dried in vacuo to give 2-(1H-benzo[dj[1,2,3jtriazol-1-yl)-2-(benzyloxycarbonylamino)aceticacid (28.6 g, 87percent) as a white solid that was used without further purification. ESI-MS m/z:327 [M+Hf
87% at 120℃; for 2 h; To a 250 mL flask equipped mechanical stirring, was added 2-oxoacetic acid hydrate (9.2 g, 0.1 mol), benzyl carbamate (15.1 g, 0.1 mol) and 1H-benzo[d][1,2,3]triazole (9.2 g, 0.1 mol), and toluene (300 mL).
The resulting solution was stirred for 2 h at 120° C. in an oil bath.
The resulting mixture was filtered and the solid residue was washed with petroleum ether (3*), and dried in vacuo to give 2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-(benzyloxycarbonylamino)acetic acid (28.6 g, 87percent) as a white solid that was used without further purification. ESI-MS m/z: 327 [M+H]+.
134.9 g for 2 h; Reflux; Dean-Stark A mixture of benzyl carbamate (82.1 g, 0.54 mol), glyoxylic acid monohydrate (50 g, 0.54 mol) and benzotriazole (64.7 g, 0.54 mol) in toluene (2.5 L) was heated at reflux with Dean and Stark water removal for 2 hours. A total of 23 mL of water was collected during the first hour before water evolution ceased. The mixture was allowed to cool to room temperature and the resulting solid filtered and washed with diethyl ether (200 mL). The damp filter cake was dried at 40 °C/50 mmHg overnight to give a cream coloured powder (134.9 g).
Reference: [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 523 - 527
[2] Patent: WO2017/15449, 2017, A1, . Location in patent: Page/Page column 51
[3] Patent: US2018/193352, 2018, A1, . Location in patent: Paragraph 0205; 0206; 0207
[4] Journal of Organic Chemistry, 1990, vol. 55, # 4, p. 2206 - 2214
[5] Journal of the Chemical Society, Chemical Communications, 1989, # 6, p. 337 - 338
[6] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 21, p. 6389 - 6392
[7] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2311 - 2319
[8] Patent: WO2004/26843, 2004, A1, . Location in patent: Page 54
[9] Patent: WO2007/34127, 2007, A1, . Location in patent: Page/Page column 27
[10] Patent: WO2016/20698, 2016, A1, . Location in patent: Page/Page column 40; 45
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  • [ 88088-95-3 ]
Reference: [1] Synthesis, 1990, # 8, p. 666 - 669
[2] Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1148 - 1152
[3] Tetrahedron Letters, 1996, vol. 37, # 3, p. 347 - 350
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Reference: [1] Heterocycles, 1983, vol. 20, # 9, p. 1787 - 1792
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  • [ 124-07-2 ]
  • [ 58068-80-7 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With 1,3,5-trichloro-2,4,6-triazine; triethylamine In dichloromethane at 0℃; for 0.5 h;
Stage #2: at 0 - 25℃; for 1 h;
General procedure: To a solution of 0.024 g TCT (0.130 mmol) in 2 cm3CH2Cl2 was added 0.033 g triethylamine (0.325 mmol) at0 C and the resulting mixture was stirred for 5 min.Carboxylic acid (0.271 mmol) was then added with continuouslystirring for 10 min. Subsequently, to this mixturewas added 0.032 g 1H-benzotriazole (0.271 mmol) and thesolution was allowed to warm up to room temperature andstirred until completion of the reaction based on TLCanalysis. The crude reaction mixture was extracted withsaturated NaHCO3, then washed with 1 M HCl and water.The combined organic layer was dried over anhydroussodium sulfate and concentrated under reduced pressure toafford the product. All known products were characterizedby 1H and 13C NMR and their spectroscopic data wereconsistent with those reported in literature
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 32, p. 7109 - 7112
[2] Monatshefte fur Chemie, 2015, vol. 146, # 6, p. 959 - 963
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  • [ 95-14-7 ]
  • [ 111-64-8 ]
  • [ 58068-80-7 ]
Reference: [1] Liebigs Annales, 1996, # 6, p. 881 - 885
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  • [ 95-14-7 ]
  • [ 50-00-0 ]
  • [ 667-27-6 ]
  • [ 103-49-1 ]
  • [ 541547-36-8 ]
Reference: [1] ACS Chemical Neuroscience, 2017, vol. 8, # 1, p. 40 - 49
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  • [ 95-14-7 ]
  • [ 4457-32-3 ]
  • [ 86832-06-6 ]
YieldReaction ConditionsOperation in experiment
59% With triethylamine In dichloromethane at 20℃; /j-Nitrobenzyloxycarbonylbenzotriazole (32a):/-Nitrobenzyl chlorofbrmate (0.5 mmol) was dissolved in 5 mL OfCH2Cl2 and treated with benzotriazole (0.5 mmol) using Et3N (2 mmol) as base. The mixture was stirred overnight at room temperature, diluted with CH2Cl2 (20 mL) and washed with 3 x 5 mL of IN HCl, 2 x 5 mL of IN NaOH and 1 x 5 mL of brine. The organic phase was dried and filtered. The volatiles were removed and the product was triturated with diethyl ether to provide a pale yellow solid (59percent yield), mp 160 - 162 0C. 1H NMR (CDCl3) δ 8.27 (d, IH5 J= 8.9 Hz), 8.17 (m, 3H), 7.72 (d, IH, J= 8.9 Hz), 7.65 (td, IH, J= 8.3 Hz, 1.1 Hz), 7.53 (m, 2H), 5.26 (s, 2H). 13C NMR (CDCl3) δ 154.84, 146.17, 142.27, 141.30, 132.01, 130.82, 128.78, 126.37, 124.16, 120.86, 113.58, 68.66. HRMS (FAB) calcd for Ci4H11N4O4 ([M+H]+): 299.0775, found 297.0775.
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 15, p. 5766 - 5775
[2] Patent: WO2008/144933, 2008, A1, . Location in patent: Page/Page column 71
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