Production Method 1

109-01-3

138500-85-3

938043-30-2

Reaction Conditions

1.1 Reagents: 4-Methylmorpholine Solvents: Tetrahydrofuran ;  35 min, 150 °C
1.2 Reagents: Tris(hydroxymethyl)aminomethane ,  Methyl isocyanate Solvents: Tetrahydrofuran ;  5 min, 150 °C

Reference

Microwave-mediated synthesis of an arylboronate library

Spencer, John; Baltus, Christine B.; Patel, Hiren; Press, Neil J.; Callear, Samantha K.; et al, ACS Combinatorial Science, 2011, 13(1), 24-31

Production Method 2

109-01-3

302348-51-2

938043-30-2

Reaction Conditions

1.1 Catalysts: Sodium carbonate ,  Bis(dichloro(η6-p-cymene)ruthenium) ,  Bis[2-(diphenylphosphino)phenyl] ether Solvents: Xylene ;  rt → 155 °C; 24 h, 155 °C

Reference

Synthesis of Amines with Pendant Boronic Esters by Borrowing Hydrogen Catalysis

Ma, Winson M. J.; James, Tony D.; Williams, Jonathan M. J., Organic Letters, 2013, 15(18), 4850-4853

Production Method 3

368879-17-8

73183-34-3

938043-30-2

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  3 h, 110 °C

Reference

Preparation of novel 3-(substituted amino)-6-alkyl-pyrazine-2-carboxamide derivatives and uses thereof

, Korea, , ,

Production Method 4

368879-17-8

73183-34-3

938043-30-2

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  3 h, 110 °C

Reference

Preparation of peptidyl nitrile compounds as dipeptidyl peptidase I (DPPI) inhibitors

, World Intellectual Property Organization, , ,

Production Method 5

368879-17-8

73183-34-3

938043-30-2

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  overnight, reflux

Reference

Preparation of peptidyl nitrile compounds as dipeptidylpeptidase I inhibitors

, World Intellectual Property Organization, , ,

Production Method 6

368879-17-8

73183-34-3

938043-30-2

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  12 h, 80 °C

Reference

Preparation of pyrrolo[2,3-b]pyridines or pyrrolo[2,3-b]pyrazines as HPK1 inhibitor and the use thereof

, World Intellectual Property Organization, , ,

Production Method 7

368879-17-8

73183-34-3

938043-30-2

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  2 h, 80 °C

Reference

Synthesis of fused heterocyclic PI3kα inhibitors treating cancers

, World Intellectual Property Organization, , ,

Production Method 8

109-01-3

138500-85-3

938043-30-2

Reaction Conditions

1.1 4 h, 70 °C

Reference

Preparation of spiro-oxazolidinone compounds and their use as metabotropic glutamate receptor potentiators

, World Intellectual Property Organization, , ,

Production Method 9

368879-17-8

73183-34-3

938043-30-2

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  rt; 12 h, 110 °C

Reference

Preparation of peptidyl nitriles as dipeptidylpeptidase I inhibitors

, World Intellectual Property Organization, , ,

Production Method 10

109-01-3

138500-85-3

938043-30-2

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Acetonitrile ;  3 h, rt
1.2 rt

Reference

Bis(het)aryl-1,2,3-triazole quinuclidines as α7 nicotinic acetylcholine receptor ligands: Synthesis, structure affinity relationships, agonism activity, [18F]-radiolabeling and PET study in rats

Ouach, Aziz; Vercouillie, Johnny; Bertrand, Emilie; Rodrigues, Nuno; Pin, Frederic; et al, European Journal of Medicinal Chemistry, 2019, 179, 449-469

Production Method 11

109-01-3

138500-85-3

938043-30-2

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetonitrile ;  4 h, rt

Reference

Structure-based design, synthesis, and evaluation of inhibitors with high selectivity for PARP-1 over PARP-2

Yu, Jiang; Luo, Lingling; Hu, Tong; Cui, Yating; Sun, Xiao; et al, European Journal of Medicinal Chemistry, 2022, 227,

Production Method 12

109-01-3

138500-85-3

938043-30-2

Reaction Conditions

1.1 Reagents: Sodium carbonate Solvents: Acetone ;  1 h, rt

Reference

Preparation of pyridine-3-sulfonamide compounds as PI3-kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 13

368879-17-8

73183-34-3

938043-30-2

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Dimethylformamide ;  overnight, 80 °C

Reference

Process for preparation of 1,5,7-tri-substituted isoquinoline derivatives and use in medicines

, World Intellectual Property Organization, , ,

Production Method 14

109-01-3

138500-85-3

938043-30-2

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  2 - 12 h, reflux

Reference

Discovery of a novel class of triazolones as Checkpoint Kinase inhibitors-Hit to lead exploration

Oza, Vibha; Ashwell, Susan; Brassil, Patrick; Breed, Jason; Deng, Chun; et al, Bioorganic & Medicinal Chemistry Letters, 2010, 20(17), 5133-5138

Production Method 15

109-01-3

138500-85-3

938043-30-2

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  45 min, rt → 80 °C

Reference

Heterocyclic compounds useful as MK2 inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases

, World Intellectual Property Organization, , ,

Production Method 16

109-01-3

138500-85-3

938043-30-2

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  20 h, rt

Reference

Preparation of bicyclic heterocyclic compounds as FGFR inhibitors

, World Intellectual Property Organization, , ,

Production Method 17

109-01-3

138500-85-3

938043-30-2

Reaction Conditions

1.1 Solvents: Diethyl ether ;  14 h, rt

Reference

Preparation of tetrazolyl (or triazolyl) substituted pyridinamines or pyrimidinamines as c-Met protein kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 18

109-01-3

138500-85-3

938043-30-2

Reaction Conditions

1.1 3 h, 70 - 75 °C; 75 °C → rt

Reference

Oxazolidinone compounds and their use as metabotropic glutamate receptor potentiators in the treatment of neurological and psychiatric disorders and preparation

, World Intellectual Property Organization, , ,

Production Method 19

938043-30-2

Reaction Conditions

Reference

4,5-Diarylisoxazole Hsp90 Chaperone Inhibitors: Potential Therapeutic Agents for the Treatment of Cancer

Brough, Paul A.; Aherne, Wynne; Barril, Xavier; Borgognoni, Jennifer; Boxall, Kathy; et al, Journal of Medicinal Chemistry, 2008, 51(2), 196-218

1-methyl-4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]piperazine Raw materials

• 1-Methylpiperazine
• 2-[4-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 1-(4-bromophenyl)methyl-4-methylpiperazine
• Bis(pinacolato)diborane
• [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol

1-methyl-4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]piperazine Preparation Products

• 1-methyl-4-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]piperazine (938043-30-2)

• 1. Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330
  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813
• 2. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
• 3. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 4. Emergence of cationic polyamine dendrimersomes: design, stimuli sensitivity and potential biomedical applications
  Partha Laskar,Christine Dufès Nanoscale Adv., 2021,3, 6007-6026
• 5. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylmethylamines

• 1221824-21-0(Dibenzyl-4-(4,4,5,5-tetramethyl-1,3,2dioxaborolan-2-yl)-benzyl-amine)
• 1012785-44-2(4-(N,N-Diethylaminomethyl)phenylboronic acid, pinacol ester)
• 1260900-80-8(3-(N,N-Diethylaminomethyl)phenylboronic acid, pinacol ester)
• 1206641-45-3(2-{Methyl-4-(4,4,5,5-tetramethyl-1,3,2dioxaborolan-2-yl)-benzyl-amino}ethanol)
• 440652-32-4(1-methyl-4-{2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenylmethyl}piperazine)
• 909391-56-6(N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine)
• 883738-27-0(1-Methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine)
• 1245505-23-0(1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine)
• 1073371-85-3(4-((N,N-Dimethylamino)methyl)phenylboronic acid pinacol ester hydrochloride)
• 878197-87-6(N,N-dimethyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine)