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Chemistry
Organic Building Blocks
Aryls
benzyl
N-(4-Bromobenzyl)acetamide
Chemistry
Organic Building Blocks
Aryls
Amines Bromides Amides Benzene Compounds
benzyl

[ CAS No. 90561-76-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 90561-76-5
Chemical Structure| 90561-76-5
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Quality Control of [ 90561-76-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 90561-76-5 ]

Product Details of [ 90561-76-5 ]

CAS No. :90561-76-5 MDL No. :MFCD14659390
Formula : C9H10BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :HBBBWKUVJSIFKV-UHFFFAOYSA-N
M.W : 228.09 Pubchem ID :15640188
Synonyms :

Calculated chemistry of [ 90561-76-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.72
TPSA : 29.1 Ų

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) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 1.64
Log Po/w (WLOGP) : 1.93
Log Po/w (MLOGP) : 2.29
Log Po/w (SILICOS-IT) : 2.38
Consensus Log Po/w : 2.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.792 mg/ml ; 0.00347 mol/l
Class : Soluble
Log S (Ali) : -1.86
Solubility : 3.12 mg/ml ; 0.0137 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -4.05
Solubility : 0.0204 mg/ml ; 0.0000893 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.02

Safety of [ 90561-76-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 90561-76-5 ]

* 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 [ 90561-76-5 ]

[ 90561-76-5 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 3959-07-7 ]
  • [ 90561-76-5 ]
Reference： [1]Shoppee [Journal of the Chemical Society, 1931, p. 1225,1232]
  • 2
  • [ 108-24-7 ]
  • [ 107047-10-9 ]
  • [ 106-38-7 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
1: 24% 2: 21% With mercury(I) chloride; tetraethylammonium bromide; mercury In acetonitrile at 25 - 30℃; cathodic reduction (-2.1V);
Reference： [1]Knittel, Dierk [Monatshefte fur Chemie, 1986, vol. 117, p. 679 - 688]
  • 3
  • [ 107047-10-9 ]
  • [ 106-38-7 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
1: 21% 2: 24% With mercury(I) chloride; tetraethylammonium bromide; mercury In acetic anhydride; acetonitrile at 25 - 30℃; cathodic reduction (-2.1V);
Reference： [1]Knittel, Dierk [Monatshefte fur Chemie, 1986, vol. 117, p. 679 - 688]
YieldReaction ConditionsOperation in experiment
Brombenzol, Formaldehyd, Acetonitril, konz. Schwefelsaeure;
Brombenzol, Paraformaldehyd (I), Acrylnitril (III), Eg. (VII), H2SO4 (VIII);
  • 5
  • [ 90561-76-5 ]
  • [ 39549-67-2 ]
YieldReaction ConditionsOperation in experiment
84% With pyridine; dipotassium peroxodisulfate; oxygen In acetonitrile at 70℃; for 16h; Sealed tube; Green chemistry; 3. Typical procedure for oxidation of N-benzylamides General procedure: N-benzylacetamide (1a) (0.0746 g, 0.5 mmol), K2S2O8 (0.1622 g, 0.6 mmol), pyridine (0.0158 g, 0.2 mmol) and CH3CN (1.0 mL) were added to an oven-dried pressure vessel with a magnetic stir bar. Then the pressure vessel was filled with dioxygen and the reaction mixture was stirred at 70 °C for 16 hours (oil bath). After the completion of the reaction, the solvent was evaporated and the reaction mixture was purified with column chromatography (eluenet: ethyl acetate/PE = 1/4) to give N-acetylbenzamide (2a) (0.073 g yield 89%).
66% With pyridine; Py-NHPI; oxygen; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 65℃; for 24h;
Reference： [1]Hu, Yixin; Zhou, Lihong; Lu, Wenjun [Synthesis, 2017, vol. 49, # 17, p. 4007 - 4016]
[2]Wang, Jia-Rui; Liu, Lei; Wang, Ye-Feng; Zhang, Ying; Deng, Wei; Guo, Qing-Xiang [Tetrahedron Letters, 2005, vol. 46, # 27, p. 4647 - 4651]
  • 6
  • [ 108-24-7 ]
  • [ 100-46-9 ]
  • [ 337535-82-7 ]
  • N-acetyl-2-bromobenzylamine [ No CAS ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
1: 21 % Spectr. 2: 16 % Spectr. 3: 15 % Spectr. Stage #1: benzylamine With bromoisocyanuric acid monosodium salt; sulfuric acid at 0℃; for 2.5h; Stage #2: acetic anhydride With pyridine at 20℃; for 2h;
Reference： [1]Yokoyama, Yuusaku; Yamaguchi, Tomotsugu; Sato, Masanori; Kobayashi, Eri; Murakami, Yasuoki; Okuno, Hiroaki [Chemical and Pharmaceutical Bulletin, 2006, vol. 54, # 12, p. 1715 - 1719]
  • 7
  • [ 153171-22-3 ]
  • [ 90561-76-5 ]
Reference： [1]Journal of the Chemical Society,1931,p. 1225,1232
[2]Patent: WO2015/103317,2015,A1
  • 8
  • [ 858011-63-9 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq.-ethanolic hydrochloric acid
Reference： [1]Shoppee [Journal of the Chemical Society, 1931, p. 1225,1232]
  • 9
  • [ 589-15-1 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 200 °C 2: aq. NaOH solution 3: aq.-ethanolic hydrochloric acid
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrazine hydrate / ethanol / 1 h / 20 °C 3: triethylamine / dichloromethane / 1 h / 20 °C
Reference： [1]Shoppee [Journal of the Chemical Society, 1931, p. 1225,1232]
[2]Current Patent Assignee: ATTUNE PHARMACEUTICALS INC; LIFESCI PHARMACEUTICALS INC - WO2015/103317, 2015, A1
  • 10
  • [ 3959-07-7 ]
  • [ 75-36-5 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
86% With triethylamine In dichloromethane at 0 - 20℃; 1. Typical procedure of preparation of N-benzylacetamide General procedure: To a stirring solution of benzylamine (4.29 g, 40 mmol), Et3N (4.45 g, 45 mmol) in CH2Cl2 (45 mL), was added acetyl chloride (3.53 g, 45 mmol) at 0 °C (ice/water bath). The reaction mixture was stirred at 0 °C for 10 minutes. Then, the reaction mixture was stirred at room temperature overnight. After the completion, the mixture was washed with NaHCO3 (3 times) and brine, and dried over MgSO4. Then, the organic layer was concentrated and recrystallized from PE-EtOAc (v/v=6/1), affording the N-benzylacetamide (1a) (5.13 g, yield 86%).
76% With triethylamine In tetrahydrofuran; dichloromethane at 0℃; for 3h; N-(4-bromobenzyl)acetamide (14) To the solution of (4-bromophenyl)methanamine (114 mg, 0.613 mmol) in dry DCM (2 mL) and dry THF (1 mL) was added trimethylamine (342 µL, 2.464 mmol). To the resulting mixture was added acetyl chloride dropwise at 0 . The mixture solution was stirred for 3 h and concentrated under a vacuum. To the residue was added DCM (20 mL), and the organic phase was washed twice with 1 N hydrochloric acid (9 mL) and saturated sodium chloride aqueous solution (10 mL). The combined organic layers were dried over Na2SO4, concentrated in a vacuum and purified by column chromatography (silica gel, DCM MeOH = 200 : 1) to give compound 14 (106 mg, 76% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.46 (d, J = 8.3 Hz, 2H), 7.17 (d, J = 8.2 Hz, 2H), 5.89 (s, 1H), 4.39 (d, J = 5.8 Hz, 2H), 2.03 (s, 3H). ESI-MS: m/z 228.0 [M+H]+.
15.a EXAMPLE 15 N-Butyloxycarbonyl-3- [4-(N-acetylaminomethyl)phenyl]-5-iso-butylthio- phene-2-sulfonamide (a) 3- [4- (N-ACETYLAMINOMETHYL) PHENYL]-5-ISO-BUTYL-N-TERT-BUTYLTHIOPHENE- 2-sulfonamide To a nitrogen-flushed solution OF PD (OAC) 2 (17.5 mg, 0. 078 mmol) in DME (2 mL), was added triphenylphosphine (82 mg, 0.312 mmol). The solution was flushed with nitrogen again and stirred under a N2 atmosphere for 30 minutes. The brownish suspension was transferred to a nitrogen-flushed mixture of 5-ISO-BUTYL-2- (N-TERT-BUTYLAMINOSULFONYL) thiophene-3-boronic acid (0.50 g, 1.56 mmol, see Preparation A, step (c)), N-(4- bromobenzyl) acetamide (0.71 g, 3.12 mmol, prepared form 4- BROMOBENZYLAMINE and acetyl chloride), and potassium carbonate (0. 86 g, 6.24 mmol) in DME: H20 : EtOH (3.5 : 1.5 : 1 mL). The mixture was refluxed overnight under a N2 atmosphere, washed with aqueous NAOH solution (1M), water and brine, dried over anhydrous MGS04 and concentrated to afford the residue which was purified by circular chromatography (50% acetone in pet. ether) to afford pure sub-title product as a colourless solid (0.43 g, 65%). mp 171-172oC H NMR (270 MHz, CDC13) : 8 0.97 (d, 6H, J= 6.60 Hz), 1.0 (s, 9H), 1.91 (M, 1H), 2.07 (s, 3H), 2.67 (d, 2H, J = 6. 93 HZ), 4.47 (d, 2H, J = 5. 61 Hz), 6.20 (br s, 1H), 6.73 (s, 1H), 7.37 (d, 2H, J = 7.92 Hz), 7.53 (d, 2H, J = 7.92 Hz) 13C NMR (67.5 MHz, CDCl3) : 6 22.13, 23.21, 29. 48, 30.50, 39. 169 43. 28, 54. 51, 127. 76, 128. 94, 129.25, 133. 88, 136. 11, 138.61, 143.14, 148. 53, 170. 18 IR (neat, cm-1): v 3314,2963, 1650,1535, 1432, 1308, 1136,1049, 1009, 844 MS (ESI+) : INLZ at 423.1 (MI++1) Anal. Calcd for C2LH30N203S2 : C, 58. 44; H, 7.24 ; N, 6.49 ; Found: C, 58.1 ; H, 7.0 ; N, 6.5
Reference： [1]Hu, Yixin; Zhou, Lihong; Lu, Wenjun [Synthesis, 2017, vol. 49, # 17, p. 4007 - 4016]
[2]Chen, Caiping; Chen, Hui; Cheng, Keguang; Li, Minglei; Liu, Jun; Liu, Shengjie; Sun, Hongbin; Wang, Yue; Wen, Xiaoan; Xu, Qing-Long; Yuan, Haoliang; Zhou, Jin; Zhou, Shuxi; Zhou, Xinyu [European Journal of Medicinal Chemistry, 2020, vol. 199]
[3]Current Patent Assignee: MCNEENEY STEPHEN PHILLIP; VICORE PHARMA - WO2004/85420, 2004, A1 Location in patent: Page 54
  • 11
  • [ 90561-76-5 ]
  • [ 163520-14-7 ]
  • [ 769966-70-3 ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate;palladium diacetate; triphenylphosphine; In 1,2-dimethoxyethane; water; ethyl acetate;Heating / reflux; To a nitrogen-flushed solution OF PD (OAC) 2 (17.5 mg, 0. 078 mmol) in DME (2 mL), was added triphenylphosphine (82 mg, 0.312 mmol). The solution was flushed with nitrogen again and stirred under a N2 atmosphere for 30 minutes. The brownish suspension was transferred to a nitrogen-flushed mixture of 5-ISO-BUTYL-2- (N-TERT-BUTYLAMINOSULFONYL) thiophene-3-boronic acid (0.50 g, 1.56 mmol, see Preparation A, step (c)), N-(4- bromobenzyl) acetamide (0.71 g, 3.12 mmol, prepared form 4- BROMOBENZYLAMINE and acetyl chloride), and potassium carbonate (0. 86 g, 6.24 mmol) in DME: H20 : EtOH (3.5 : 1.5 : 1 mL). The mixture was refluxed overnight under a N2 atmosphere, washed with aqueous NAOH solution (1M), water and brine, dried over anhydrous MGS04 and concentrated to afford the residue which was purified by circular chromatography (50% acetone in pet. ether) to afford pure sub-title product as a colourless solid (0.43 g, 65%). mp 171-172oC H NMR (270 MHz, CDC13) : 8 0.97 (d, 6H, J= 6.60 Hz), 1.0 (s, 9H), 1.91 (M, 1H), 2.07 (s, 3H), 2.67 (d, 2H, J = 6. 93 HZ), 4.47 (d, 2H, J = 5. 61 Hz), 6.20 (br s, 1H), 6.73 (s, 1H), 7.37 (d, 2H, J = 7.92 Hz), 7.53 (d, 2H, J = 7.92 Hz) 13C NMR (67.5 MHz, CDCl3) : 6 22.13, 23.21, 29. 48, 30.50, 39. 169 43. 28, 54. 51, 127. 76, 128. 94, 129.25, 133. 88, 136. 11, 138.61, 143.14, 148. 53, 170. 18 IR (neat, cm-1): v 3314,2963, 1650,1535, 1432, 1308, 1136,1049, 1009, 844 MS (ESI+) : INLZ at 423.1 (MI++1) Anal. Calcd for C2LH30N203S2 : C, 58. 44; H, 7.24 ; N, 6.49 ; Found: C, 58.1 ; H, 7.0 ; N, 6.5
Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 7166 - 7183
[2]Patent: WO2004/85420,2004,A1 .Location in patent: Page 54-55
  • 12
  • [ 90561-76-5 ]
  • [ 62-53-3 ]
  • [ 909281-40-9 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; Inert atmosphere;
Reference： [1]Location in patent: experimental part Caiazzo, Aldo; Garcia, Paula M. L.; Wever, Ron; Van Hest, Jan C. M.; Rowan, Alan E.; Reek, Joost N. H. [Organic and Biomolecular Chemistry, 2009, vol. 7, # 14, p. 2926 - 2932]
  • 13
  • [ 90561-76-5 ]
  • [ 62-53-3 ]
  • [ 588-46-5 ]
  • [ 909281-40-9 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; Inert atmosphere;
Reference： [1]Location in patent: experimental part Caiazzo, Aldo; Garcia, Paula M. L.; Wever, Ron; Van Hest, Jan C. M.; Rowan, Alan E.; Reek, Joost N. H. [Organic and Biomolecular Chemistry, 2009, vol. 7, # 14, p. 2926 - 2932]
  • 14
  • [ 3959-07-7 ]
  • [ 141-78-6 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
87% With Novozym 435 In toluene at 100℃; Inert atmosphere; Enzymatic reaction;
Reference： [1]Location in patent: experimental part Caiazzo, Aldo; Garcia, Paula M. L.; Wever, Ron; Van Hest, Jan C. M.; Rowan, Alan E.; Reek, Joost N. H. [Organic and Biomolecular Chemistry, 2009, vol. 7, # 14, p. 2926 - 2932]
  • 15
  • [ 26177-44-6 ]
  • [ 75-36-5 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In dichloromethane; at 0 - 30℃; for 2h; Step 48a: N-(4-bromobenzyl)acetamide (Compound 0601-135)To the solution of <strong>[26177-44-6]4-bromobenzylamine hydrochloride</strong> (1.2 g, 5.4 mmol) and Et3N (5.5 g, 54 mmol) in dichloromethane (10 mL) was added CH3COCl (555 mg, 7.02 mmol) at 0 C and stirred for 2 hr at 30 C. Then the mixture was concentrated and the residue was dissolved in CH2C12 (30 mL), washed with water, dried over Na2S04 and concentrated to obtain 0601-135 (1.3 g, 100%) as a yellow solid. LCMS: 228 [M+l]+, 1H NMR (400 MHz, OMSO-d6) delta 2.00 (s, 3H), 4.33 (d, J= 6.4 Hz, 2H), 6.26 (s, 1H), 7.13 (d, J= 8.4 Hz, 2H), 7.43 (d, J= 8.4 Hz, 2H).
100% With triethylamine; In dichloromethane; at 0 - 30℃; for 2h; Step 48a: N-(4-bromobenzyl)acetamide (Compound 0601-135)[0394]To the solution of <strong>[26177-44-6]4-bromobenzylamine hydrochloride</strong> (1.2 g, 5.4 mmol) and Et3N (5.5 g, 54 mmol) in dichloromethane (10 mL) was added CH3COCl (555 mg, 7.02 mmol) at 0 C. and stirred for 2 hr at 30 C. Then the mixture was concentrated and the residue was dissolved in CH2Cl2 (30 mL), washed with water, dried over Na2SO4 and concentrated to obtain 0601-135 (1.3 g, 100%) as a yellow solid. LCMS: 228 [M+1]+, 1H NMR (400 MHz, DMSO-d6) delta 2.00 (s, 3H), 4.33 (d, J=6.4 Hz, 2H), 6.26 (s, 1H), 7.13 (d, J=8.4 Hz, 2H), 7.43 (d, J=8.4 Hz, 2H).
100% With triethylamine; In dichloromethane; at 0 - 30℃; for 2h; With the addition of dichloromethane (10mL) solution of 4-bromobenzyl amine hydrochloric acid (1.2g, 5.4mmol) and Et3N (5.5g, 54mmol) solution to CH3COCl (555mg, 7.02mmol) of at 0 , 2 hours at 30 and the mixture was stirred. Then the mixture concentrated, the residue was dissolved in CH2Cl2 (30mL), washed with water, dried over Na2SO4, to give a 0601-135 as a yellow solid concentration (1.3g, 100%).
Reference： [1]Patent: WO2011/130628,2011,A1 .Location in patent: Page/Page column 183-184
[2]Patent: US2013/102595,2013,A1 .Location in patent: Paragraph 0393; 0394
[3]Patent: JP2015/187145,2015,A .Location in patent: Paragraph 0342
  • 16
  • [ 873-75-6 ]
  • [ 75-05-8 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
93% With silica-bonded N-propylsulphamic acid In neat (no solvent) at 80℃; for 1h; Green chemistry;
Reference： [1]Shakeri, Maryam-Sadat; Tajik, Hassan; Niknam, Khodabakhsh [Journal of Chemical Sciences, 2012, vol. 124, # 5, p. 1025 - 1032]
  • 17
  • [ 3959-07-7 ]
  • [ 108-24-7 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
1.5 g With triethylamine In dichloromethane at 20℃; for 1h; 164 To a solution of 4-bromo-benzylamine (2.83 g, 15.3 mmol, 1.0 eq) in DCM (50 mL) was added the AC2O (2.34 g, 23.0 mmol, 1.5 eq) and Et3N (2.34 g, 23.0 mmol, 1.5 eq). The reaction mixture was stirred for 1 h at rt The solvent was evaporated, and water was added, and the mixture was extracted with EtOAc. The organic layer was dried over Na2S04 and evaporated to give the crude product which was subject to silica gel chromatography (PE/ EA = 5/ 1 - 2/ 1) to afford N-(4-bromo-benzyl)-acetamide as a white solid (1.5 g, 43%). 1 H NMR (DMSO-ifc, 400 2 H), 7.50 (d, 2 H), 8.36 (s, 1 H).
Reference： [1]Current Patent Assignee: ATTUNE PHARMACEUTICALS INC; LIFESCI PHARMACEUTICALS INC - WO2015/103317, 2015, A1 Location in patent: Page/Page column 272
  • 18
  • [ 90561-76-5 ]
  • methyl 5-(chloromethyl)pyridine-3-carboxylate [ No CAS ]
  • methyl 5-(4-(acetamidomethyl)benzyl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: N-(4-bromo-benzyl)-acetamide With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 80℃; for 12h; Stage #2: methyl 5-(chloromethyl)pyridine-3-carboxylate With sodium carbonate In 1,4-dioxane; water at 95℃; for 2h; 164 To a solution of N-(4-bromo-benzyl)-acetamide (1.5 g, 6.6 mmol, 1.0 eq) in dioxane (40 mL) was added 4,4,5,5,4',4',5',5'-octamethyl-[2,2']bi[[l,3,2]dioxaborolanyl] (1.7 g, 6.6 mmol,1.0 eq), Pd(dppf)Cl2CH2Ci2 (0.29 g, 0.66 mmol, 0.1 eq) and AcOK (1.94 g, 19.8 mmol, 3.0 eq). The mixture was stirred at 80 °C for 12 h and allowed to cool to rt Then to this mixture was added 5-chloromethyl-nicotinic acid methyl ester (1.47 g, 6.6 mmol, 1.0 eq), NaCOs (2.12 g, 0.19.8 mmol, 3.0 eq) and H20 (8 mL). The mixture was stirred at 95 °C for 2 h and allowed cool to rt The reaction mixture was extracted with EtOAc (100 mLx3). The organic layer was dried over Na2S04 and evaporated to give the crude product which was subject to silica gel chromatography (PE/ EA = 5/ 1 - 2/ 1) to afford 5-[4-(acetylamino-methyl)-benzyl] -nicotinic acid methyl ester as a yellow solid (1.2 g, 61%).' H NMR (DMSO-ifc, 300 MHz): δ 1.84 (s, 3 H), 3.86 (s, 3 H), 4.04 (s, 2 H), 4.19 (d, 2 H), 7.17-7.25 (m, 4H), 8.09 (t, 2 H), 8.30 (s, 1 H), 8.75 (d, 2 H), 8.91 (d, 2 H).
Reference： [1]Current Patent Assignee: ATTUNE PHARMACEUTICALS INC; LIFESCI PHARMACEUTICALS INC - WO2015/103317, 2015, A1 Location in patent: Page/Page column 272
  • 19
  • [ 90561-76-5 ]
  • 5-(4-(acetamidomethyl)benzyl)-N-((3-chloro-1H-indol-5-yl)methyl)nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bis(pinacol)diborane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / 80 °C 1.2: 2 h / 95 °C 2.1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C 3.1: HATU; triethylamine / N,N-dimethyl-formamide / 20 °C
Reference： [1]Current Patent Assignee: ATTUNE PHARMACEUTICALS INC; LIFESCI PHARMACEUTICALS INC - WO2015/103317, 2015, A1
  • 20
  • [ 90561-76-5 ]
  • 5-(4-(acetamidomethyl)benzyl)nicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis(pinacol)diborane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / 80 °C 1.2: 2 h / 95 °C 2.1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C
Reference： [1]Current Patent Assignee: ATTUNE PHARMACEUTICALS INC; LIFESCI PHARMACEUTICALS INC - WO2015/103317, 2015, A1
  • 21
  • [ 90561-76-5 ]
  • 5-(4-(acetamidomethyl)benzyl)-N-((3-chloro-6-fluoro-1H-indol-5-yl)methyl)pyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bis(pinacol)diborane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / 80 °C 1.2: 2 h / 95 °C 2.1: lithium hydroxide; water / tetrahydrofuran / 2 h / 20 °C 3.1: HATU; triethylamine / N,N-dimethyl-formamide / 20 °C
Reference： [1]Current Patent Assignee: ATTUNE PHARMACEUTICALS INC; LIFESCI PHARMACEUTICALS INC - WO2015/103317, 2015, A1
  • 22
  • [ 201230-82-2 ]
  • [ 80-43-3 ]
  • [ 3959-07-7 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
65% With copper (II)-fluoride; 1,10-Phenanthroline In chlorobenzene at 140℃; for 24h; Sealed tube; Autoclave; Inert atmosphere;
Reference： [1]Li, Yahui; Wang, Changsheng; Zhu, Fengxiang; Wang, Zechao; François Soulé, Jean; Dixneuf, Pierre H.; Wu, Xiao-Feng [Chemical Communications, 2017, vol. 53, # 1, p. 142 - 144]
  • 23
  • [ 90561-76-5 ]
  • methyl 4-((4-((3-(4-(acetamidomethyl)phenyl)-2-methyl-7-oxo-2,7-dihydro-6H-pyrazolo[4,3-d]pyrimidin-6-yl)methyl)-4-hydroxypiperidin-1-yl)methyl)-3-chlorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere; Sealed tube 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / N,N-dimethyl-formamide / 19 h / 110 °C / Inert atmosphere
Reference： [1]Chen, Caiping; Chen, Hui; Cheng, Keguang; Li, Minglei; Liu, Jun; Liu, Shengjie; Sun, Hongbin; Wang, Yue; Wen, Xiaoan; Xu, Qing-Long; Yuan, Haoliang; Zhou, Jin; Zhou, Shuxi; Zhou, Xinyu [European Journal of Medicinal Chemistry, 2020, vol. 199]
  • 24
  • [ 90561-76-5 ]
  • [ 73183-34-3 ]
  • [ 1235450-93-7 ]
YieldReaction ConditionsOperation in experiment
95% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80℃; for 3h;Inert atmosphere; Sealed tube; General procedure: A sealed tube was charged with 13 (200 mg, 0.7 mmol), bis(neopentylglycolato)diboron (197 mg, 0.77 mmol), AcOK (304 mg, 3.1 mmol), and DMSO (3.5 mL). The resulting suspension was deoxygenated by sparging with nitrogen gas. Pd(dppf)Cl2 (17 mg, 0.021 mmol) was added, and the tube was sealed tightly and heated at 80 C for 3 h. Water (6 mL) was added, and the mixture was extracted with EtOAc (3 mL × 3), washed with brine (3 mL × 3), and dried over MgSO4. The organic layer was concentrated in a vacuum, and the residue was puried by column chromatography (silica gel, petroleum ether : EtOAc = 5 : 1) to give compound 15 as a white solid (37 mg, 16% yield).
Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 199
  • 25
  • [ 106-38-7 ]
  • [ 75-05-8 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
67% With trisaminocyclopropenium; lithium hydroxide monohydrate; tetra-n-butylammonium hexafluoridophosphate; trifluoroacetic acid at 20℃; for 48h; Inert atmosphere; Irradiation; Electrochemical reaction;
0.087 g With lithium hydroxide monohydrate In dichloromethane at 23℃; Electrochemical reaction; 4.2 General electrolysis procedure General procedure: Amino acid (6.6 mmol), CH2Cl2:H2O (13:1) as solvent and KBr + Et4NBF4 (3.3 mmol) as mediator and background salt were placed into electrochemical cell at 23°C. The electrolysis time is 9 hours (at a constant current of 80 mA). After passing 4F/mol of electricity, arene (0.66 mmol) was added to the reaction mixture and another 2F/mol of electricity (at a constant current of 40 mA) was passed. At the end of electrolysis the reaction mixture was first filtered to remove potassium bromide and then was evaporated on rotary evaporator. The residue was purified through passing through chromatographic column with silica gel (hexane-ethyl acetate).
Reference： [1]Lambert, Tristan H.; Shen, Tao [Journal of the American Chemical Society, 2021, vol. 143, # 23, p. 8597 - 8602]
[2]Strekalova, Sofia; Kononov, Alexander; Budnikova, Yulia [Tetrahedron Letters, 2022, vol. 102]
  • 26
  • [ 90561-76-5 ]
  • tert-butyl 2-oxo-3-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate [ No CAS ]
  • N-(4-((2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)methyl)benzyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With chloro(2-dicyclohexylphosphino-2’,6’-dimethoxy-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II); caesium carbonate In 1,4-dioxane; water at 80℃; for 17h; Inert atmosphere; 11.A Step A: N-(4-((2-oxo-2,3-dihydro-lH-benzo[d]imidazol-l-yl)methyl)benzyl)acetamide N-(4-bromobenzyl)acetamide (6.09 g, 26.7 mmol), cesium carbonate (26.1 g, 80 mmol), sSPhos Pd G2 (2.198 g, 2.67 mmol), and tert-butyl 2-oxo-3 -((4, 4,5,5 -tetram ethyl- 1,3,2- dioxaborolan-2-yl)methyl)-2,3-dihydro-lH-benzo[d]imidazole-l-carboxylate (10 g, 26.7 mmol) (Intermediate 1) were added to a round bottom flask equipped with a stir bar. The mixture was purged with nitrogen for 5 minutes. After 5 minutes, dioxane (81 ml) and water (8.10 ml) were added to the mixture. The reaction mixture was heated to 80 °C for 17 hours, while stirring. After 17 hours, the mixture was cooled to room temperature and concentrated under reduced pressure. Ethyl acetate was added, and the reaction mixture was washed with water. The combined organics were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The material was dissolved in THF (40 ml), HC1 (4 M in dioxane) (40 ml, 160 mmol) was added dropwise to the solution. The mixture was heated to 45 °C for 45 minutes. After 45 minutes, the material was filtered, to afford the title compound. LC/MS (m/z): 296 (M+H)+.
With chloro(2-dicyclohexylphosphino-2’,6’-dimethoxy-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II); caesium carbonate In 1,4-dioxane; water at 80℃; for 17h; Inert atmosphere; 11.A Step A: N-(4-((2-oxo-2,3-dihydro-lH-benzo[d]imidazol-l-yl)methyl)benzyl)acetamide N-(4-bromobenzyl)acetamide (6.09 g, 26.7 mmol), cesium carbonate (26.1 g, 80 mmol), sSPhos Pd G2 (2.198 g, 2.67 mmol), and tert-butyl 2-oxo-3 -((4, 4,5,5 -tetram ethyl- 1,3,2- dioxaborolan-2-yl)methyl)-2,3-dihydro-lH-benzo[d]imidazole-l-carboxylate (10 g, 26.7 mmol) (Intermediate 1) were added to a round bottom flask equipped with a stir bar. The mixture was purged with nitrogen for 5 minutes. After 5 minutes, dioxane (81 ml) and water (8.10 ml) were added to the mixture. The reaction mixture was heated to 80 °C for 17 hours, while stirring. After 17 hours, the mixture was cooled to room temperature and concentrated under reduced pressure. Ethyl acetate was added, and the reaction mixture was washed with water. The combined organics were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The material was dissolved in THF (40 ml), HC1 (4 M in dioxane) (40 ml, 160 mmol) was added dropwise to the solution. The mixture was heated to 45 °C for 45 minutes. After 45 minutes, the material was filtered, to afford the title compound. LC/MS (m/z): 296 (M+H)+.
Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2021/226003, 2021, A1 Location in patent: Page/Page column 80-81
[2]Current Patent Assignee: MERCK & CO INC - WO2021/226003, 2021, A1 Location in patent: Page/Page column 80-81
  • 27
  • [ 74-90-8 ]
  • [ 586-76-5 ]
  • [ 90561-76-5 ]
YieldReaction ConditionsOperation in experiment
35% With iodobenzene; water; toluene-4-sulfonic acid; Selectfluor at 25℃; for 16h; Irradiation; Inert atmosphere;
Reference： [1]Narobe, Rok; Murugesan, Kathiravan; Schmid, Simon; König, Burkhard [ACS Catalysis, 2022, vol. 12, # 1, p. 809 - 817]

Tags: 90561-76-5 synthesis path| 90561-76-5 SDS| 90561-76-5 COA| 90561-76-5 purity| 90561-76-5 application| 90561-76-5 NMR| 90561-76-5 COA| 90561-76-5 structure

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