[ CAS No. 235426-30-9 ] {[proInfo.proName]}

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Quality Control of [ 235426-30-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 235426-30-9 ]

Product Details of [ 235426-30-9 ]

CAS No. :	235426-30-9	MDL No. :	MFCD06659903
Formula :	C₅H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	175.03	Pubchem ID :	-
Synonyms :

Safety of [ 235426-30-9 ]

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

Application In Synthesis of [ 235426-30-9 ]

* 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 [ 235426-30-9 ]

[ 235426-30-9 ] Synthesis Path-Downstream 1~16

1
[ 6338-45-0 ]
[ 60-29-7 ]
[ 506-68-3 ]
[ 235426-30-9 ]

Reference： [1]Langenbeck [Journal fur praktische Chemie (Leipzig 1954), 1928, vol. <2> 119, p. 79]

2
[ 235426-30-9 ]
[ 105983-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	beim Nitrieren;
	durch Nitrierung;

Reference： [1]Langenbeck [Journal fur praktische Chemie (Leipzig 1954), 1928, vol. <2> 119, p. 79]
[2]Langenbeck [Journal fur praktische Chemie (Leipzig 1954), 1928, vol. <2> 119, p. 79]

3
[ 6338-45-0 ]
[ 235426-30-9 ]

Yield	Reaction Conditions	Operation in experiment
29%	With bromocyane In acetonitrile Ambient temperature;

Reference： [1]McCallum, Peter B.W.; Weavers, Rex T.; Grimmett, M. Ross; Blackman, Allan G. [Australian Journal of Chemistry, 1999, vol. 52, # 3, p. 159 - 165]

4
[ 6338-45-0 ]
[ 235426-30-9 ]

Reference： [1]Langenbeck [Journal fur praktische Chemie (Leipzig 1954), 1928, vol. <2> 119, p. 79]

5
[ 235426-30-9 ]
[ 1201641-36-2 ]
[ 1201641-37-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In methanol at 120℃; for 0.5h; Microwave irradiation; Inert atmosphere;	34.ii Step ii) N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(l,4-dimethyl-lH-imidazol-2- yl)phenethoxy)propanamide N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenethoxy)propanamide [Example 34, Step i)] (390 mg), potassium carbonate (220 mg), Pd(Ph3P)4 (46 mg) and 2-bromo-l,4-dimethyl-lH-imidazole (279 mg) in MeOH (3 mL) was loaded into a microwave vial, flushed with nitrogen and sealed. The vial was heated within a Discover microwave at 1200C for 30 min. After cooling, the reaction and the filtrate washed with DCM. Volatiles were removed and the residue purified on silica using 20% - 100% EtOAc/ iso gradient to afford the subtitled compound (358 mg).MS [M+H]+ = 458 (MultiMode+)1H NMR (400 MHz, CDCl3) δ 7.51 - 7.47 (m, IH), 7.43 - 7.40 (m, IH), 7.37 - 7.30 (m, IH), 7.27 - 7.22 (m, IH), 6.67 (s, IH), 4.61 and 4.37 ( 2 x t, J = 5.2 Hz, IH), 4.25 - 4.16 and 3.61 - 3.51 ( 2 x m, IH), 3.81 - 3.74 (m, 2H), 3.73 - 3.65 (m, 2H), 3.68 (s, 3H), 3.41 (s, 3H), 3.39 (s, 3H), 3.37 and 3.29 ( 2 x d, J = 4.9 Hz, 2H), 2.96 - 2.89 (m, 2H), 2.73 - 2.65 (m, 2H), 2.26 (s, 3H), 1.85 - 1.74 (m, 2H), 1.73 - 1.05 (m, 8H); a -2:1 mixture of rotamers is observed.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2009/154557, 2009, A1 Location in patent: Page/Page column 143-144

6
[ 235426-30-9 ]
[ 1040275-42-0 ]
C₂₆H₃₅N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; N,N-dimethyl-formamide at 110℃; for 4h;

Reference： [1]Eda, Masahiro; Kuroda, Tomoko; Kaneko, Satoshi; Aoki, Yoshiyuki; Yamashita, Masami; Okumura, Chieko; Ikeda, Yoshitaka; Ohbora, Tomoko; Sakaue, Masaki; Koyama, Natsumi; Aritomo, Keiichi [Journal of Medicinal Chemistry, 2015, vol. 58, # 12, p. 4918 - 4926]

7
[ 235426-30-9 ]
2-(2-isopropylphenyl)-7-methyl-9-(piperidin-4-ylmethyl)-7,9-dihydro-8H-purin-8-one [ No CAS ]
9-((1-(1,4-dimethyl-1H-imidazol-2-yl)piperidin-4-yl)methyl)-2-(2-isopropylphenyl)-7-methyl-7,9-dihydro-8H-purin-8-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 220℃; for 0.5h; Microwave irradiation;	43 9-((l-(l,4-Dimethyl-lH-imidazol-2-yl)piperidin-4-yl)methyl)-2-(2-isopropylphi methyl-7,9-dihydro-8H-purin-8-one (1-501) 9-((l-(l,4-Dimethyl-lH-imidazol-2-yl)piperidin-4-yl)methyl)-2-(2-isopropylphi methyl-7,9-dihydro-8H-purin-8-one (1-501) A mixture of Intermediate B-80 (0.2M solution in pyridine, 150 μ, 30 μιηο) and (1999) 2-bromo-l,4-dimethyl-lH-imidazole (0.2M solution in pyridine, 300 μ, 60 μιηο) was heated for 30 min at 220 °C in a Biotage Initiator microwave. After cooling to ambient temperature, the volatiles were removed under reduced pressure. The residue was treated with IN NaOH (0.5 mL) and the mixture extracted with EtOAc (2 x 0.5 mL). The volatiles were removed under reduced pressure and the residue was purified using mass-triggered preparatory HPLC to afford 9-((l-(l,4-Dimethyl-lH-imidazol-2-yl)piperidin-4-yl)methyl)-2-(2-isopropylphenyl)-7-methyl- 7,9-dihydro-8H-purin-8-one (1-501). LCMS Rt (min): 0.9096, m/z 460.48 [M+H]+.

Reference： [1]Current Patent Assignee: FORMA THERAPEUTICS, INC. - WO2017/87837, 2017, A1 Location in patent: Paragraph 00521

8
[ 235426-30-9 ]
N-(2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-methylmethanesulfonamide [ No CAS ]
C₁₃H₁₈N₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.78%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 110℃; for 2h;	175 Synthesis of compound 175.1 To a mixture of compound 2-bromo-1,4-dimethyl-1H- imidazole (1 g, 3 .Ommol, 1. Oeq) and N-(2-amino-5-(4,4,5, 5-tetramethyl- 1,3 ,2-dioxaborolan-2- yl)phenyl)-N-methylmethane-Sulfonamide (0.8g, 4.5mmol, 1.5eq) in a mixture of dioxane (0.8mL) and water (0.2mL), potassium carbonate (1.2g, 0.9lmmol, 3.Oeq) was added. Reaction mixture was degassed for 15 mm and then stirred at 110 °C for 2h. After completion of the reaction, the reaction mixture was transferred to water and extracted with ethyl acetate. Organic layer were combined, dried over Na2SO4, filtered and concentrated in vacuo to get the crude material. This was purified by column chromatography using 8% ethyl acetate in hexane as eluant to obtain 175.1 (0.4g, 23.78%). MS(ES): m/z 295.47 [M+H]t

Reference： [1]Current Patent Assignee: NIMBUS THERAPEUTICS INC - WO2018/75937, 2018, A1 Location in patent: Paragraph 00905; 00906

9
[ 235426-30-9 ]
1-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-1H-pyrazole-5-carboxamide [ No CAS ]
N-(4-(1,4-dimethyl-1H-imidazol-2-yl)benzyl)-1-methyl-1H-pyrazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 110℃; for 2h; Microwave irradiation; Sealed tube;

Reference： [1]Le, Thuy G.; Kundu, Abhijit; Ghoshal, Atanu; Nguyen, Nghi H.; Preston, Sarah; Jiao, Yaqing; Ruan, Banfeng; Xue, Lian; Huang, Fei; Keiser, Jennifer; Hofmann, Andreas; Chang, Bill C. H.; Garcia-Bustos, Jose; Jabbar, Abdul; Wells, Timothy N. C.; Palmer, Michael J.; Gasser, Robin B.; Baell, Jonathan B. [Journal of Medicinal Chemistry, 2018, vol. 61, # 23, p. 10875 - 10894]

10
[ 235426-30-9 ]
[ 2935-90-2 ]
methyl 3-((1,4-dimethyl-1H-imidazol-2-yl)thio)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate In N,N-dimethyl acetamide at 20℃; for 16h; Inert atmosphere; Irradiation;

Reference： [1]Sandfort, Frederik; Knecht, Tobias; Pinkert, Tobias; Daniliuc, Constantin G.; Glorius, Frank [Journal of the American Chemical Society, 2020, vol. 142, # 15, p. 6913 - 6919]

11
[ 235426-30-9 ]
7-chloro-2-(3,5-dimethoxybenzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
7-chloro-2-(3,5-dimethoxybenzyl)-5-(1,4-dimethyl-1H-imidazol-2-yl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); potassium carbonate In water; toluene at 110℃; Inert atmosphere;	A Step A. Preparation of 7-chloro-2-(3,5-dimethoxybenzyl)-5-(l,4-dimethyl-l/ - imidazol-2-yl)-3,4-dihydroisoquinolin-l(2/ )-one To a mixture of 7-chloro-2-(3,5- dimethoxybenzyl)-5-(4,4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin- l(2H)-one (Intermediate 25, 192 mg, 0.42 mmol), 2-bromo-l,4-dimethyl- lH-imidazole (88 mg, 0.5 mmol), K2CO3 (116 mg, 0.84 mmol), and toluene (6 mL)/water (0.5 mL) was added 4-(di- tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium (9 mg, 0.013 mmol). The resulting mixture was degassed and back filled with Argon, and heated at 110 °C overnight. The solvent was removed under reduced pressure. The residue was purified by flash chromatography (Combi-flash Rf, Hex/EtOAc = 10-100% gradient) to afford the title compound (94 mg, 52%). NMR (400 MHz, CDCh) d 8.22 (s, 1H), 7.44 (s, 1H), 6.69 (s, 1H), 6.45 (d, J= 2.0 Hz, 2H), 6.37 (m, 1H),4.71 (s, 2H), 3.77 (s, 6H), 3.47 (s, 3H), 3.42 (t, J = 6.4 Hz, 2H), 2.85 (t, J= 6.4 Hz, 2H), 2.23 (s, 3H).

Reference： [1]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2020/86857, 2020, A1 Location in patent: Paragraph 00238

12
[ 235426-30-9 ]
[ 146631-00-7 ]
2-(4-(benzyloxy)phenyl)-1,4-dimethyl-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 18h;	1 Step 1. 2-(4-(benzyloxy)phenyl)-l,4-dimethyl-lH-imidazole [00203] To a solution of (4-(benzyloxy)phenyl)boronic acid (1.30 g, 5.70 mmol) in 1,4- dioxane (20 mL) was added 2-bromo-l, 4-dimethyl- lH-imidazole (1.00 g, 5.71 mmol), Pd(dppf)Cl2 (417 mg, 0.58 mmol), potassium carbonate (1.60 g, 11.6 mmol), and water (6 mL). The resulting mixture was stirred for 18 h at 100 °C and then cooled to rt. The reaction mixture was poured into water (20 mL) and then extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The resulting crude product was purified by silica gel chromatography (eluting with 0: 100 to 40:60 ethyl acetate/petroleum ether) to afford 2-(4-(benzyloxy)phenyl)-l,4-dimethyl- lH-imidazole as a black solid (1.00 g, 63%). LCMS (ESI, m/z ) 279 [M+H]+.

Reference： [1]Current Patent Assignee: FORMA THERAPEUTICS, INC. - WO2020/139988, 2020, A1 Location in patent: Paragraph 00203

13
[ 235426-30-9 ]
4-(1,4-dimethyl-1H-imidazol-2-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 18 h / 100 °C 2: hydrogen; palladium 10% on activated carbon / ethanol / 3 h / 20 °C

Reference： [1]Current Patent Assignee: FORMA THERAPEUTICS, INC. - WO2020/139988, 2020, A1

14
[ 235426-30-9 ]
4-(1,4-dimethyl-1H-imidazol-2-yl)phenyl trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 18 h / 100 °C 2: hydrogen; palladium 10% on activated carbon / ethanol / 3 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: FORMA THERAPEUTICS, INC. - WO2020/139988, 2020, A1

15
[ 235426-30-9 ]
1,4-dimethyl-1H-imidazole-2-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thiourea In tetrahydrofuran at 100℃; for 0.333333h; Sealed tube; Microwave irradiation; Inert atmosphere;

Reference： [1]Garrison, Aaron T.; Orsi, Douglas L.; Capstick, Rory A.; Whomble, David; Li, Jinming; Carter, Trever R.; Felts, Andrew S.; Vinson, Paige N.; Rodriguez, Alice L.; Han, Allie; Hajari, Krishma; Cho, Hyekyung P.; Teal, Laura B.; Ragland, Madeline G.; Ghamari-Langroudi, Masoud; Bubser, Michael; Chang, Sichen; Schnetz-Boutaud, Nathalie C.; Boutaud, Olivier; Blobaum, Anna L.; Foster, Daniel J.; Niswender, Colleen M.; Conn, P. Jeffrey; Lindsley, Craig W.; Jones, Carrie K.; Han, Changho [Journal of Medicinal Chemistry, 2022, vol. 65, # 8, p. 6273 - 6286]

16
[ 235426-30-9 ]
1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)-4-(((1,4-dimethyl-1H-imidazol-2-yl)thio)methyl)piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thiourea / tetrahydrofuran / 0.33 h / 100 °C / Sealed tube; Microwave irradiation; Inert atmosphere 2: Cs₂CO₃ / N,N-dimethyl-formamide / 0.5 h / Sealed tube; Microwave irradiation; Inert atmosphere; Heating

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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. 235426-30-9 ] {[proInfo.proName]}

Quality Control of [ 235426-30-9 ]

Related Doc. of [ 235426-30-9 ]

Product Details of [ 235426-30-9 ]

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Application In Synthesis of [ 235426-30-9 ]

[ 235426-30-9 ] Synthesis Path-Downstream 1~16

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