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Quality Control of [ 78-39-7 ]

COA NMR CNMR HPLC LC-MS

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Product Citations

Building bioorthogonal click-release capable artificial receptors on cancer cell surface for imaging, drug targeting and delivery

Chen, Jing ; Ji, Peng ; Gnawali, Giri , et al. APSB,2023,13(6):2736-2746. DOI: 10.1016/j.apsb.2022.12.018 PubMed ID: 37425049

Abstract: The current targeting drug delivery mainly relies on cancer cell surface receptors. However, in many cases, binding affinities between protein receptors and homing ligands is relatively low and the expression level between cancer and normal cells is not significant. Distinct from conventional targeting strategies, we have developed a general cancer targeting platform by building artificial receptor on cancer cell surface via a chemical remodeling of cell surface glycans. A new tetrazine (Tz) functionalized chemical receptor has been designed and efficiently installed on cancer cell surface as "overexpressed" biomarker through a metabolic glycan engineering. Different from the reported bioconjugation for drug targeting, the tetrazine labeled cancer cells not only locally activate TCO-caged prodrugs but also release active drugs via the unique bioorthogonal Tz-TCO click-release reaction. The studies have demonstrated that the new drug targeting strategy enables local activation of prodrug, which ultimately leads to effective and safe cancer therapy.

Keywords: Artificial receptor ; Click and release ; Local activation ; Protein degradation

Purchased from AmBeed: 3212-75-7 ; 5505-63-5 ; 25316-40-9 ; 1345866-66-1 ; 2645443-13-4 ; 501-52-0 ; 1949837-12-0 ; 107-96-0 ; 78-39-7 ; 67131-33-3 ; 2915291-31-3

Product Details of [ 78-39-7 ]

CAS No. :	78-39-7	MDL No. :	MFCD00009223
Formula :	C₈H₁₈O₃	Boiling Point :	-
Linear Structure Formula :	CH₃C(OCH₂CH₃)₃	InChI Key :	-
M.W :	162.23	Pubchem ID :	-
Synonyms :

Safety of [ 78-39-7 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P403+P235	UN#:	3272
Hazard Statements:	H225	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 78-39-7 ]

* 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 [ 78-39-7 ]
Downstream synthetic route of [ 78-39-7 ]

[ 78-39-7 ] Synthesis Path-Upstream 1~3

1
[ 16867-03-1 ]
[ 78-39-7 ]
[ 86467-39-2 ]

Yield	Reaction Conditions	Operation in experiment
65.8%	Stage #1: at 120℃; for 4 h; Stage #2: Cooling	80 mL of ethyl orthoacetate was added to 15 g (136 mmol) of 2-amino-3-hydroxypyridine, followed by addition of p-toluenesulfonic acid in a catalytic amount, and the mixture was reacted at 120° C. for 4 hours. After the reaction solution was cooled, triethylamine was added to the solution, to neutralize p-toluenesulfonic acid. Then, the solution was subjected to distillation under reduced pressure by using an evaporator, and then purified by silica gel column chromatography.Amount of the product: 12.0 g, Yield: 65.8percent.

Reference： [1] Monatshefte fur Chemie, 2011, vol. 142, # 1, p. 87 - 91
[2] Heterocycles, 1995, vol. 41, # 3, p. 477 - 486
[3] Monatshefte fur Chemie, 2007, vol. 138, # 7, p. 663 - 667
[4] Patent: US2009/247736, 2009, A1, . Location in patent: Page/Page column 13
[5] Tetrahedron Letters, 1990, vol. 31, # 8, p. 1155 - 1156
[6] Synthetic Communications, 1992, vol. 22, # 20, p. 2891 - 2901

2
[ 78-39-7 ]
[ 5202-85-7 ]
[ 7142-09-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With acetic acid In ethanol at 110℃; for 24 h; Inert atmosphere; Sealed tube	General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2–3 equiv) and absolute ethanol (2–3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 °C for 12–72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5percentether in pentane. The following compounds were prepared:

Reference： [1] Molecules, 2018, vol. 23, # 11,

3
[ 78-39-7 ]
[ 63286-28-2 ]
[ 68774-78-7 ]

Yield	Reaction Conditions	Operation in experiment
2 g	Reflux	Step 2: 8-chloro-3-methyl-[l,2,4]triazolo[4,3-a]pyrazine [0197] To a stirred solution of 2-chloro-3-hydrazinylpyrazine (2.0 g, 14 mmol) in xylene (20 mL) was added triethyl orthoformate (5.8 mL, 32 mmol). The mixture was heated under reflux overnight and then cooled to room temperature. The resulting precipitate was collected by filtration to afford the title compound as a brown powder (2.0 g, 87percent). MS (ESI) calcd forC₆H₅CIN₄: 168.0 ; found: 169.2 [M+H]. *H NM (400 MHz, CDCI₃) δ 7.80 (d, J = 4.8 Hz, 1H), 7.71 (d, J = 4.8 Hz, 1H), 2.83 (s, 3H).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 20, p. 4606 - 4613
[2] Patent: WO2016/100349, 2016, A2, . Location in patent: Paragraph 0197

[ 78-39-7 ] Synthesis Path-Downstream 1~14

1
[ 22972-51-6 ]
[ 78-39-7 ]
[ 107602-58-4 ]

Reference： [1]Helvetica Chimica Acta,1986,vol. 69,p. 2026 - 2037

2
[ 51806-20-3 ]
alcoholic KOH [ No CAS ]
[ 141-78-6 ]
[ 78-39-7 ]
[ 621-63-6 ]

Reference： [1]Journal of the American Chemical Society,1936,vol. 58,p. 531

3
[ 452-58-4 ]
[ 78-39-7 ]
[ 68175-07-5 ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 1719 - 1722
[2]Tetrahedron Letters,2009,vol. 50,p. 1828 - 1833
[3]Journal of Chemical Research - Part S,2000,p. 584 - 585

4
[ 480-63-7 ]
[ 78-39-7 ]
[ 1754-55-8 ]

Reference： [1]Synthetic Communications,2002,vol. 32,p. 2209 - 2213
[2]Tetrahedron,2006,vol. 62,p. 1309 - 1317

5
[ 623-57-4 ]
[ 78-39-7 ]
[ 951247-78-2 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4269 - 4278

6
[ 71682-97-8 ]
[ 78-39-7 ]
2-(3,4-Difluorobenzoyl)-3-hydroxycrotononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; water;	EXAMPLE 55 2-(3,4-Difluorobenzoyl)-3-hydroxycrotononitrile A solution of 10.2 g. of <strong>[71682-97-8]3,4-difluorobenzoylacetonitrile</strong>, 9.2 g. of triethyl orthoacetate and 20 ml. of acetic anhyride is heated on a steam bath for 0.5 hour and then poured into 200 ml. of water which is then heated on the steam bath for 2 hours. On cooling, the solid is filtered and then dissolved in methylene chloride. This solution is extracted with two portions of aqueous sodium bicarbonate and the aqueous extracts are combined and acidified with concentrated hydrochloric acid. The precipitate is extracted into methylene chloride, passed through a pad of Magnesol.(R)., heated and diluted with hexane. Upon cooling, colorless crystals result, yielding the title compound, m.p. 51°-54° C. Similarly prepared are 2-(2,5-difluorobenzoyl)-3-hydroxycrotononitrile, 2-(3,4,5-trimethoxybenzoyl)-3-hydroxycrotononitrile, 2-(2,4,6-trimethylbenzoyl)-3-hydroxycrotononitrile, and 2-(2,5-dichlorobenzoyl)-3-hydroxycrotononitrile.

Reference： [1]Patent: US4173650,1979,A

7
[ 89415-54-3 ]
[ 78-39-7 ]
[ 92260-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 140℃; for 38.5h;	A solution of 5-bromo-N2-methyl-pyridine-2 3-diamine (Stage 67.1.4, 960 mg, 4 75 mmol) in triethylorthoacetate (Aldrich, Buchs, Switzerland, 25 ml) was stirred for 38 5 h at 140C. The reaction mixture was evaporated to dryness. The residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over Na2SO4, filtered and evaprated. The crude product was dry loaded on silica gel and purified by MPLC (DCM/MeOH 0% - 4%) to give the title compound as a brown solid (HPLC. tR 1 95 mm (Method A); M+H = 226, 228 MS-ES).
	With acetic acid; at 80℃; for 2h;	To a suspension of <strong>[89415-54-3]5-bromo-N2-methylpyridine-2,3-diamine</strong> (510 mg, 2.51 mmol) in AcOH (20 mL) was added MeC(OEt)3 (1 mL) and the solution was warmed to 80 C. for 2 hours. The reaction mixture was allowed to cool to room temperature and was concentrated in vacuo. The crude residue was purified by silica gel column chromatography (0-25% THF/CH2Cl2 gradient) to afford the desired product. 1H NMR (400 MHz, CDCl3) delta 8.36 (d, J=1.8 Hz, 1H), 8.06 (d, J=1.9 Hz, 1H), 3.80 (s, 3H), 2.65 (s, 3H).

Reference： [1]Patent: WO2010/139731,2010,A1 .Location in patent: Page/Page column 181-182
[2]Patent: US2013/281433,2013,A1 .Location in patent: Paragraph 1373

8
[ 38191-34-3 ]
[ 78-39-7 ]
[ 151230-42-1 ]

Yield	Reaction Conditions	Operation in experiment
88.5%	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; at 25.0℃; for 0.166667h;	2-Amino-5-bromophenol (561 mg, 3.00 mmol)Was added to triethyl orthoacetate (656 muL, 3.6 mmol),1,3-Dibromo-5,5-dimethylhydantoin (17.2 mg, 6.00 × 10 -2 mmol) was added,And the mixture was stirred at room temperature for 10 minutes.And extracted with ethyl acetate (50 mL × 2).The organic layer was washed with saturated brine,After dehydration with anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure,The residue was subjected to silica gel column chromatography using ethyl acetate / hexane (1/4 (volume ratio)) as an elution solvent,Compound 16 was obtained in a yield of 560 mg (88.5%).
65%	With acetic acid; for 0.5h;Reflux;	To 2-amino-5- bromophenol ( l .OOg, 5.32 mmol) , acetic acid ((0.006 ml) and triethylorthoacetate ( 1.75 ml, 9.58 mmol) were added and refluxed for 3o min. The reaction mixture was quenched with water, extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate : petroleum ether to afford the title compound as a orange solid ((0.756 g, 65%). -NMR (delta ppm, CDC13, 400 MHz): delta 7.64 (d, 7 = 1.7 Hz, 1 H), 7.51 (d, 7 = 8.4 Hz, 1 H), 7.43 (dd, 7 = 8.4, 1.7 Hz, 1 H), 2.67 (s, 3H).
65%	With acetic acid; for 0.5h;Reflux;	Intermediate 126 6-bromo-2-methylbenzo[d]oxazole: To 2-amino-5-bromophenol (1.00 g, 5.32 mmol), acetic acid ((0.006 ml) and triethylorthoacetate (1.75 ml, 9.58 mmol) were added and refluxed for 30 min. The reaction mixture was quenched with water, extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate: petroleum ether to afford the title compound as a orange solid ((0.756 g, 65%). 1H-NMR (delta ppm, CDCl3, 400 MHz): delta 7.64 (d, J=1.7 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.43 (dd, J=8.4, 1.7 Hz, 1H), 2.67 (s, 3H).

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 7241 - 7257
[2]Patent: JP2016/79108,2016,A .Location in patent: Paragraph 0063
[3]Patent: WO2012/151525,2012,A1 .Location in patent: Page/Page column 128
[4]Patent: US2012/289496,2012,A1 .Location in patent: Page/Page column 113

9
[ 78-39-7 ]
[ 121-88-0 ]
[ 5683-43-2 ]

Reference： [1]ARKIVOC,2012,vol. 2012,p. 262 - 279

10
[ 570-08-1 ]
[ 78-39-7 ]
[ 3044-06-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With zinc(II) chloride; at 95℃; for 4h;Inert atmosphere;	a) diethyl 2-(1-ethoxyethylidene)malonate. A mixture of diethyl 2-acetylmalonate (10 g, 0.049 mol), 1 , 1 ,1 -triethoxyethane (24 g, 0.15 mol) and ZnCI2 (70 mg, 0.0049 mol) was stirred at 95 C for 4 h under an inert atmosphere. The mixture was concentrated and the residue was purified by silica gel chromatography (10% pet. ether in ethyl acetate) to give the desired product as an oil (6.4 g, 56%). LC/MS: MS (ES+) m/e 231 (MH+); 1H NMR (300 MHz, CDCI3) delta ppm 1.22-1.33 (m, 9 H), 2.43 (s, 3H), 4.06 (q, J = 6.9 Hz, 2 H), 4.16 (q, J = 7.2 Hz, 2 H), 4.26 (q, J = 7.2 Hz, 2 H).

Reference： [1]Patent: WO2013/96153,2013,A1 .Location in patent: Page/Page column 162

11
[ 1575-36-6 ]
[ 78-39-7 ]
[ 20223-87-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3794 - 3797

12
[ 39549-79-6 ]
[ 78-39-7 ]
[ 194473-09-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With acetic acid; In ethanol; at 110℃; for 24h;Inert atmosphere; Sealed tube;	General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2?3 equiv) and absolute ethanol (2?3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 °C for 12?72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5percentether in pentane. The following compounds were prepared:2,7-Dimethylquinazolin-4(3H)-one (8a). This compound was prepared from<strong>[39549-79-6]2-amino-4-methylbenzamide</strong> (100 mg, 0.67 mmol), triethyl orthoacetate (217 mg, 245 L, 1.34 mmol)and acetic acid (121 mg, 115 L, 2.01 mmol) in absolute ethanol (2 mL) at 110 °C for 24 h to give105 mg (90percent) as a white solid, m.p. 260?262 °C (lit [49] m.p. 263?264 °C); IR (CHCl3): 3169, 1677 cm-1;1H-NMR (400 MHz, CDCl3): delta 11.6 (br s, 1H), 8.16 (d, J = 8.1 Hz, 1H), 7.47 (br s, 1H), 7.29 (dd, J =8.1, 1.0 Hz, 1H), 2.57 (s, 3H), 2.51 (s, 3H); 13C-NMR (101 MHz, CDCl3): delta 163.9, 153.2, 149.5, 146.0,128.0, 126.8, 126.1, 117.9, 22.1, 22.0; HRMS (ESI): m/z for C10H10N2O [M + 1]+: calcd.: 175.0871; found:175.0867.

Reference： [1]Molecules,2018,vol. 23

13
[ 5900-59-4 ]
[ 78-39-7 ]
[ 7012-88-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With acetic acid; In ethanol; at 110℃; for 24h;Inert atmosphere; Sealed tube;	General procedure: The 2-aminobenzamide (1 equiv), the orthoester (2?3 equiv) and absolute ethanol (2?3 mL) wereplaced in a 15-mL Chemglass screw-cap pressure tube (No. CG-1880-01, Chemglass, Vineland, NJ,USA). Glacial acetic acid (3 equiv) was added, N2 was introduced to the vessel and the cap wastightened. The vessel was heated at 110 °C for 12?72 h, then cooled and concentrated to give thequinazolinone, which was purified by crystallization from absolute ethanol or trituration from 5percentether in pentane. The following compounds were prepared:

Reference： [1]Molecules,2018,vol. 23

14
[ 40925-68-6 ]
[ 78-39-7 ]
[ 5676-56-2 ]

Yield	Reaction Conditions	Operation in experiment
59%	at 100℃; for 6h;	[0339] Compound 8e: A solution of Comp-8d (15 g, 79.78 mmol) in 1,1,1-triethoxy ethane (75 mL) was heated at 100C for 6h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated in vacuo and the crude obtained was purified by column chromatography (silica, 100-200 mesh, 10% Ethyl acetate in Hexane) to afford 5-bromo-2-methylbenzo[d]oxazole (8e; 10 g, 59%) as a yellow solid. (0602) [0340] MS (ESI) m/e [M+H]+ Rt %: 211.95/1.93/93.3%. (0603) [0341] XH NMR (400 MHz, CDCl3) delta 2.65 (s, 3H) 7.33 - 7.37 (m, 1H) 7.39 - 7.44 (m, 1H) 7.79 (s, l

Reference： [1]Patent: WO2019/152731,2019,A1 .Location in patent: Paragraph 0339-0341

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Code	Phrase
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P222	Do not allow contact with air.
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P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 78-39-7 ] {[proInfo.proName]}

Quality Control of [ 78-39-7 ]

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Product Details of [ 78-39-7 ]

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[ 78-39-7 ] Synthesis Path-Upstream 1~3

[ 78-39-7 ] Synthesis Path-Downstream 1~14

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Ethers

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[ 78-39-7 ]