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Quality Control of [ 1711-06-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1711-06-4 ]

SDS Specification

Alternatived Products of [ 1711-06-4 ]

Product Citations

Selective and Cell-Active PBRM1 Bromodomain Inhibitors Discovered through NMR Fragment Screening

Shifali Shishodia ; Raymundo Nu?ez ; Brayden P. Strohmier , et al. J. Med. Chem.,2022,65(20):13714-13735. DOI: 10.1021/acs.jmedchem.2c00864 PubMed ID: 36227159

Abstract: PBRM1 is a subunit of the PBAF

Purchased 2 mM. Structure–activity relationship studies on the tightest-binding hit resulted in nanomolar inhibitors with selectivity for PBRM1 over SMARCA2 and SMARCA4. These chemical probes inhibit the association of full-length PBRM1 to acetylated histone peptides and selectively inhibit growth of a PBRM1-dependent prostate cancer cell line.

from AmBeed: class="">77326-36-4 ; class="">104-87-0 ; class="">2148-56-3 ; class="">63329-53-3 ; class="">1591-37-3 ; class="">387-45-1 ; class="">936-08-3 ; class="">1123-56-4 ; class="">2819989-75-6 ; class="">703-80-0 ; class="">1885-29-6 ; class="">115643-59-9 ; class="">15764-16-6 ; class="">487-68-3 ; class="span_more span_less">145737-61-7 ; class="span_more span_less">5779-95-3 ; class="span_more span_less">88-68-6 ; class="span_more span_less">6575-11-7 ; class="span_more span_less">77326-62-6 ; class="span_more span_less">88-65-3 ; class="span_more span_less">4635-59-0 ; class="span_more span_less">5779-94-2 ; class="span_more span_less">56043-01-7 ; class="span_more span_less">5779-93-1 ; class="span_more span_less">1591-38-4 ; class="span_more span_less">446-52-6 ; class="span_more span_less">62803-47-8 ; class="span_more span_less">1885-31-0 ; class="span_more span_less">620-23-5 ; class="span_more span_less">54166-95-9 ; class="span_more span_less">22179-72-2 ; class="span_more span_less">529-20-4 ; class="span_more span_less">100-52-7 ; class="span_more span_less">123-11-5 ; class="span_more span_less">1711-06-4 ; class="span_more span_less">454-89-7 ; class="span_more span_less">170875-01-1 ; class="span_more span_less">883032-29-9 ; class="span_more span_less">2819989-61-0 ; class="span_more span_less">1915012-21-3 ; class="span_more span_less">2819989-58-5 ; class="span_more span_less">2819989-60-9 ; class="span_more span_less">2819989-57-4 ; class="span_more span_less">2819989-68-7 ; class="span_more span_less">2819989-67-6 ; class="span_more span_less">111478-13-8 ; class="span_more span_less">73096-42-1 ; class="span_more span_less">2835-78-1 ; class="span_more span_less">118-92-3 ; class="span_more span_less">22458-07-7 ; class="span_more span_less">80258-99-7 ; class="span_more span_less">24782-64-7 ; class="span_more span_less">1108790-90-4 ; class="span_more span_less">175204-03-2 ; class="span_more span_less">97-96-1 ; class="span_more span_less">780802-33-7 ; class="span_more span_less">89-98-5 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

Product Details of [ 1711-06-4 ]

CAS No. :	1711-06-4	MDL No. :	MFCD00000681
Formula :	C₈H₇ClO	Boiling Point :	-
Linear Structure Formula :	CH₃C₆H₄C(O)Cl	InChI Key :	YHOYYHYBFSYOSQ-UHFFFAOYSA-N
M.W :	154.59	Pubchem ID :	74375
Synonyms :

Calculated chemistry of [ 1711-06-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.59
TPSA :	17.07 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.02
Log Po/w (XLOGP3) :	3.35
Log Po/w (WLOGP) :	2.37
Log Po/w (MLOGP) :	2.37
Log Po/w (SILICOS-IT) :	2.8
Consensus Log Po/w :	2.58

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.29
Solubility :	0.0798 mg/ml ; 0.000516 mol/l
Class :	Soluble
Log S (Ali) :	-3.39
Solubility :	0.0636 mg/ml ; 0.000411 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.33
Solubility :	0.0718 mg/ml ; 0.000465 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.1

Safety of [ 1711-06-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1711-06-4 ]

* 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 [ 1711-06-4 ]
Downstream synthetic route of [ 1711-06-4 ]

[ 1711-06-4 ] Synthesis Path-Upstream 1~1

1
[ 393-52-2 ]
[ 1711-06-4 ]
[ 80277-41-4 ]
[ 5955-74-8 ]

Reference： [1] Patent: US6359156, 2002, B1, . Location in patent: Page column 10

[ 1711-06-4 ] Synthesis Path-Downstream 1~10

1
[ 109-89-7 ]
[ 1711-06-4 ]
[ 134-62-3 ]

Yield	Reaction Conditions	Operation in experiment
97.5%	With sodium hydroxide; In water; at 45℃; for 0.05h;	438.8 g (6 mol) of diethylamine and 1052 g of an aqueous sodium hydroxide solution (19%) were mixed and stirred.Forming a diethylamine-hydrogen peroxide system, m-methylbenzoyl chloride is an acid chloride system,The two systems were injected into the reactor through a metering pump at a flow rate of 45 ml/min and 35 ml/min, respectively, where n (m-methylbenzoyl chloride): n (diethylamine) = 1:2,Using the microchannel reactor of Figure 2, the temperature is controlled at 45 C and the residence time is 180 s.The quantitative collection reaction solution is transferred to a separatory funnel for separation.The organic phase was retained and the aqueous phase was extracted three times with diethyl ether.Drying over anhydrous sodium sulfate, distilling off diethyl ether to give a crude product.After distillation under reduced pressure, fractions of 165 to 175 C were collected.A pale yellow liquid was obtained, and the yield of the product calculated by weighing was 97.5%.Chromatographic detection The purity of the product was 98.3%.

Reference： [1]Patent: CN107840805,2018,A .Location in patent: Paragraph 0032; 0035; 0038; 0041; 0044; 0047-0050; 0053
[2]Chemical Abstracts,1930,vol. 24,p. 94
Chemisches Zentralblatt,1929,vol. 100,p. 2324
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 1225 - 1228
[4]Journal of the American Chemical Society,2014,vol. 136,p. 10258 - 10261
[5]Chemical Science,2019,vol. 10,p. 7399 - 7406

2
[ 35441-10-2 ]
[ 1711-06-4 ]
3-Methyl-benzoic acid 5-cyano-6-oxo-1,6-dihydro-pyridin-2-yl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1498 - 1506

3
[ 40963-14-2 ]
[ 1711-06-4 ]
[ 100594-35-2 ]

Yield	Reaction Conditions	Operation in experiment
	With trimethylamine; In tetrahydrofuran; water;	EXAMPLE 6 (Reference) Preparation of (+-)-N-(1-carbamoyl-1,2-dimethylpropyl)-m-toluamide To a solution containing 26 g (0.20 mol), (+-)-<strong>[40963-14-2]2-amino-2,3-dimethylbutyramide</strong> and 30.7 ml trimethylamine in 200 ml dry tetrahydrofuran at 0c is added dropwise 26.4 ml (0.20 mol) m -toluoyl chloride. The temperature is kept below 15C. After the addition, stirring is continued for one hour at room temperature. The mixture is poured into 300 ml ice-cold water. The product is collected by filtration, washed with water and air dried to give 52.3 g of crude products. A 4.0 g sample is recrystallized from methylene chloride-hexane to give 2.58 g of analytically pure (+-)-N-(1-carbamoyl-1,2-dimethylpropyl)- m -toluamide, mp 186.5-187.5C. When (+)-<strong>[40963-14-2]2-amino-2,3-dimethylbutyramide</strong> is used in place of the racemic material, the product is (-)-N-(1-carbamoyl-1,2-dimethylpropyl)- m -toluamide, mp 164C-179C, [alpha] [25/D ] = -39.32 (C = 0.0509 g/ml methanol).

Reference： [1]Patent: EP158000,1991,B1

4
[ 33332-28-4 ]
[ 1711-06-4 ]
[ 1194688-06-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With pyridine; at 100℃; for 16h;	Example 24; N-(6-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyrazin-2-yl)-3-methylbenzamide; Example 24A; N-(6-chloropyrazin-2-yl)-3-methylbenzamide; <strong>[33332-28-4]2-Amino-6-chloropyrazin</strong>e (496.0 mg, 3.83 mmol) was dissolved in pyridine (15 mL). 3-Methylbenzoyl chloride (760 muL, 5.77 mmol) was added to the reaction mixture. The reaction was heated to 100° C. for 16 h then concentrated under vacuum. The residue was partitioned between 1M K2CO3 (50 mL) and CH2Cl2 (4.x.50 mL). The organic extracts were combined, washed with and brine (50 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (5percent EtOAc in CH2Cl2, Rf=0.39) to afford the title compound as a white solid (919.0 mg, 97percent). MS m/z 248 (M+H)+.

Reference： [1]Patent: US2009/281118,2009,A1 .Location in patent: Page/Page column 17

5
[ 21109-25-1 ]
[ 1711-06-4 ]
C₁₇H₁₆N₂O [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 4266 - 4269

6
[ 1081-04-5 ]
[ 1711-06-4 ]
[ 1448314-55-3 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6259 - 6272

7
[ 22259-53-6 ]
[ 1711-06-4 ]
[ 1328004-79-0 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2426 - 2429

8
[ 1260637-54-4 ]
[ 1711-06-4 ]
methyl-2-(3-methylbenzamido)-2-(tetrahydro-2H-pyran-4-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With triethylamine; In dichloromethane; for 1.0h;	To a suspension of <strong>[1260637-54-4]methyl-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetate hydrochloride</strong> (210 mg, 1.0 mmol)in dichloromethane (20 ml)was added triethylamine (303 mg, 3.0 mmol). To the mixturewas added dropwisea solution of 3-methylbenzoyl chloride(170 mg, 1.1 mmol) in dichloromethane (5 ml)at15 0CThe mixturewas stirred for 1 hour before the reaction was quenched with ice-water (10 ml). The organic layer was collectedand the aqueous layer was extracted with ethyl acetate (3 x20 ml). The combined organiclayers were dried over anhydroussodium sulfate and the solventwas removed under reduced pressure.The residue was purified by silica gel column chromatography eluting with ethyl acetate: petroleum ether= 1:1 to afford methyl-2-(3-methylbenzamido)-2-(tetrahydro-2H-pyran-4-20 yl)acetate as a colorless oil (200- mg, 68%). LCMS (ESI): m/z = 292.1 (M+Ht1H-NMR (300 MHz, CDCI3): o = 1.45-1.71 (m, 4H), 2.10-2.25 (m, 1H), 2.41 (s, 3H), 3.31-3.46 (m, 2H),3.80 (s ,3H), 3.91-4.06 (m, 2H), 4.83-4.94(m, 1H), 6.61-6.75(m, 1H), 7.31-7.34(m, 2H), 7.51-7.68 (m, 2H).

Reference： [1]Patent: WO2015/154023,2015,A1 .Location in patent: Page/Page column 99; 100; 101

9
[ 1351813-02-9 ]
[ 1711-06-4 ]
(6-bromo-5-nitro-1H-indazol-1-yl)(m-tolyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With triethylamine; In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; at 0 - 20℃;	General procedure: To 5-Nitroindazole derivative (0.2 g) in DCM (10 mL), mixture of triethylamine (1.1 equiv.) and benzoyl chloride or its derivative (1.1 equiv.) was slowly added and stirred at 0C 5-10 min and then stirred at room temperature for overnight. The reaction progress is monitored by the TLC. The reaction mass was extracted with dichloromethane (DCM) (3X10 mL) and organic layer was dried with MgSO4 and evaporated followed by the purification by column chromatography (EtOAc: Hexane = 1: 4 ~ 1: 6) to give corresponding N-benzoylindazole derivatives (6a-j).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2604 - 2608

10
[ 116668-47-4 ]
[ 1711-06-4 ]
C₁₉H₁₅NO₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 7697 - 7707

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Catalytic Hydrogenation ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Robinson Annulation ? Rosenmund Reduction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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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

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[ CAS No. 1711-06-4 ] {[proInfo.proName]}

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[ 1711-06-4 ] Synthesis Path-Upstream 1~1

[ 1711-06-4 ] Synthesis Path-Downstream 1~10

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Aryls

Chlorides

Acyl Chlorides

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[ 1711-06-4 ]