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Chemistry
Organic Building Blocks
Amines
cyclopentane
(Aminomethyl)cyclopentane
Chemistry
Organic Building Blocks
Amines
Aliphatic Cyclic Hydrocarbons
cyclopentane
aminomethyl

[ CAS No. 6053-81-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 6053-81-2
Chemical Structure| 6053-81-2
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Quality Control of [ 6053-81-2 ]

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Product Details of [ 6053-81-2 ]

CAS No. :6053-81-2 MDL No. :MFCD04114081
Formula : C6H13N Boiling Point : -
Linear Structure Formula :- InChI Key :UBLYEVLMRSPMOG-UHFFFAOYSA-N
M.W : 99.17 Pubchem ID :80153
Synonyms :

Safety of [ 6053-81-2 ]

Signal Word:Danger Class:3,8
Precautionary Statements:P210-P261-P280-P305+P351+P338 UN#:2924
Hazard Statements:H225-H302-H315-H318-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 6053-81-2 ]

* 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 [ 6053-81-2 ]

[ 6053-81-2 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 1123-00-8 ]
  • [ 6053-81-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogen azide; chloroform
Reference： [1]v. Braun; Anton [Chemische Berichte, 1933, vol. 66, p. 1373,1375] Ney et al. [Journal of the American Chemical Society, 1943, vol. 65, p. 770,775]
  • 2
  • [ 3217-94-5 ]
  • [ 6053-81-2 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: cyclopentylamide With bis(cyclopentadienyl)dihydrozirconium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; Glovebox; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water for 2h; Glovebox; Inert atmosphere; 2. Experimental General procedure: In a nitrogen-filled glovebox, to a 15 mL reaction tube equipped with a magnetic stirrer, were added Cp2ZrH2 (0.01mmol, 2.2 mg) as the catalyst, and the appropriate amide (0.2mmol); solvent was added when necessary. HBpin (3 equiv. peramide functional group) was then added, and the reaction tube was taken out from the glovebox and stirred at room temperature for 12-48 h. The resultant crude amines were either isolated using silica gel flash chromatography, or acidified by stirring with HCl in Et2O (2 mL, 1N) for 2 h, after which time precipitation was observed. Then, the reaction solution was transferred to a centrifuge tube and centrifuged three times. The supernatant was removed and the resulting solid was dried inan oven at 80 °C for several hours to obtain the HCl salt of the amine.
With lithium aluminium tetrahydride
Reference： [1]Han, Bo; Jiao, Haijun; Wu, Lipeng; Zhang, Jiong [Cuihua Xuebao/Chinese Journal of Catalysis, 2021, vol. 42, # 11, p. 2059 - 2067]
[2]Westland; Merz; Alexander; Newton; Bauer; Conway; Barton; Khullar; Devdhar; Grenan [Journal of medicinal chemistry, 1972, vol. 15, # 12, p. 1313 - 1321] Cogdell,T.J. [Journal of Organic Chemistry, 1972, vol. 37, # 16, p. 2541 - 2545]
  • 3
  • [ 1670-82-2 ]
  • [ 6053-81-2 ]
  • [ 104447-78-1 ]
YieldReaction ConditionsOperation in experiment
42% 199.d EXAMPLE 199 (d) Indole-6-carboxylic acid was reacted with 1-cyclopentylmethylamine using a similar procedure to that described for indole GG in Example 193 to give 6-N-(cyclopentylmethyl)carbamoylindole (II) in 42% yield as a pale pink powder; NMR: 3.19 (d,2H,CH2 NH), 6.46 (d,1H, H3 -indole), 7.91 (d,1H,H7 -indole), 8.29 (t,1H,CH2 NH).
With 1,1'-carbonyldiimidazole 1.) CH2Cl2, reflux, 30 min, 2.) CH2Cl2, reflux, 30 min; Yield given. Multistep reaction;
Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US4997844, 1991, A
[2]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 4
  • [ 1670-81-1 ]
  • [ 6053-81-2 ]
  • [ 110707-71-6 ]
YieldReaction ConditionsOperation in experiment
80% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 12h;
73% With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 48h; Ambient temperature;
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
[2]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
  • 5
  • [ 6053-81-2 ]
  • [ 145889-27-6 ]
  • [ 110707-74-9 ]
YieldReaction ConditionsOperation in experiment
93% With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 48h; Ambient temperature;
Reference： [1]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
  • 6
  • [ 4254-02-8 ]
  • [ 6053-81-2 ]
YieldReaction ConditionsOperation in experiment
84% With sodium sulfate 13.a 2-[5-(N-Cyclopentylmethylcarbamoyl)-3-[2-methoxy-4-[2-(phenylsulphonyl)acetyl]benzyl]indol-1-yl]-N,N-dimethylpropionamide (a) A solution of cyclopentylnitrile (15 g) in ether (115 ml) was added dropwise, under nitrogen, to a refluxing slurry of lithium aluminum hydride (9 g) in ether (200 ml). The mixture was treated with a saturated aqueous solution of sodium sulfate and filtered. The filtrate was dried (MgSO4) and evaporated to give cyclopentylmethylamine (13 g, 84%) as a yellow liquid; IR (neat): 3300, 3340, 1600 cm-1.
77% With ammonia; hydrogen In water; isopropyl alcohol at 80℃; for 24h; Autoclave;
54% With borane-THF In tetrahydrofuran for 18h; Heating;
With borane In tetrahydrofuran for 18h; Heating;
With methanol; sodium for 5h;
With LiAlH4 In diethyl ether 3.A Synthesis of Compound 116 A. Aminomethylcyclopentane. To a solution of LiAlH4 (38 g, 1.0 mole) in diethyl ether (2 L) was added cyclopentanecarbonitrile (73.2 g, 0.77 mol) as a solution in 250 mL ether. The solution was stirred overnight at ambient temperature and then quenched by addition of the organics to 3 L of a saturated potassium, sodium tartrate solution. The amine was extracted into 3 L of ether, dried over anhydrous K2 CO3 then concentrated by distillation to approximately 400 mL total volume. The crude product was purified via distillation to give 58.2 g of the title compound as a colorless oil. (1 H)-NMR (CDCl3) consistent with structure.
58.2 g With lithium aluminium tetrahydride In diethyl ether at 20℃;
With LiAlH4 In diethyl ether 114.A Aminomethylcyclopentane A. Aminomethylcyclopentane To a solution of LiAlH4 (38 g, 1.0 mole) in diethyl ether (2L) was added cyclopentanecarbonitrile (73.2 g, 0.77 mol) as a solution in 250 mL ether. The solution was stirred overnight at ambient temperature and then quenched by addition of the organics to 3L of a saturated potassium, sodium tartrate solution. The amine was extracted into 3L of ether, dried over anhydrous K2 CO3 then concentrated by distillation to approximately 400 mL total volume. The crude product was purified via distillation to give 58.2 g of the title compound as a colorless oil. (1 H)-NMR (CDCl3) consistent with structure.
With LiAlH4 In diethyl ether 114.A A. A. Aminomethylcyclopentane To a solution of LiAlH4 (38 g, 1.0 mole) in diethyl ether (2 L) was added cyclopentanecarbonitrile (73.2 g, 0.77 mol) as a solution in 250 mL ether. The solution was stirred overnight at ambient temperature and then quenched by addition of the organics to 3 L of a saturated potassium, sodium tartrate solution. The amine was extracted into 3 L of ether, dried over anhydrous K2 CO3 then concentrated by distillation to approximately 400 mL total volume. The crude product was purified via distillation to give 58.2 g of the title compound as a colorless oil. (1 H)-NMR (CDCl3) consistent with structure.
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino]ruthenium(II); hydrogen In isopropyl alcohol at 100℃; for 3h; Autoclave; chemoselective reaction;
Stage #1: cyclopentanecarbonitrile With lithium aluminium tetrahydride In diethyl ether at 20℃; for 24.17h; Stage #2: With sodium hydroxide; water In diethyl ether at 0℃; Intermediate 104: CvclopentylmethylamineTo a 1.0M solution of lithium aluminium hydride in dry diethyl ether (27 ml) at RT was added a solution of cyclopentanecarbonitrile (2 g) in dry diethyl ether (10 ml) dropwise over 10 minutes. The purple solution was stirred at RT for 24 hours. The resulting pink solution was cooled to O0C and 5.0M sodium hydroxide solution (10 ml) was added slowly until effervescence ceased. The reaction was filtered from the white precipitate that had formed. The filtrate was dried over magnesium sulphate, filtered and concentrated in vacuo (RT, 200 mbar) to afford the title compound as a clear oil (1.6 g).1H NMR ((CDa)2SO): δ 2.63 (2H, d), 1.92 (1 H, m), 1.77 (2H, m), 1.57 (4H, m), 1.18 (2H, m). NH2 protons not observed.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US4837235, 1989, A
[2]Formenti, Dario; Mocci, Rita; Atia, Hanan; Dastgir, Sarim; Anwar, Muhammad; Bachmann, Stephan; Scalone, Michelangelo; Junge, Kathrin; Beller, Matthias [Chemistry - A European Journal, 2020, vol. 26, # 67, p. 15589 - 15595]
[3]Flosi, William J.; DeGoey, David A.; Grampovnik, David J.; Chen, Hui-ju; Klein, Larry L.; Dekhtyar, Tatyana; Masse, Sherie; Marsh, Kennan C.; Mo, Hong Mei; Kempf, Dale [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6695 - 6712]
[4]Kelley, James L.; Morris Bullock; Krochmal, Mark P.; McLean, Ed W.; Linn, James A.; Durcan, Micheal J.; Cooper, Barrett R. [Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3207 - 3216]
[5]Larsen, Janus S.; Pedersen, Erik B.; Nielsen, Claus [Synthesis, 2004, # 11, p. 1874 - 1878]
[6]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US5723490, 1998, A
[7]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US6372778, 2002, B1 Location in patent: Example 114
[8]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US5585397, 1996, A
[9]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US5783701, 1998, A
[10]Neumann, Jacob; Bornschein, Christoph; Jiao, Haijun; Junge, Kathrin; Beller, Matthias [European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 5944 - 5948]
[11]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2008/101867, 2008, A1 Location in patent: Page/Page column 105
  • 7
  • [ 6053-81-2 ]
  • [ 7782-77-6 ]
  • [ 3637-61-4 ]
  • [ 1462-03-9 ]
  • [ 108-93-0 ]
Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 4564,4567
  • 8
  • [ 6053-81-2 ]
  • [ 87119-03-7 ]
  • [ 437717-31-2 ]
YieldReaction ConditionsOperation in experiment
70% In methanol at 25℃; Electrolysis;
Reference： [1]Largeron, Martine; Neudorffer, Anne; Vuilhorgne, Marc; Blattes, Estelle; Fleury, Maurice-Bernard [Angewandte Chemie - International Edition, 2002, vol. 41, # 5, p. 824 - 827]
  • 9
  • [ 6053-81-2 ]
  • 2-amino-4-benzoyl-3-hydroxy-phenol anion [ No CAS ]
  • [ 437717-31-2 ]
  • C19H19NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 70% 2: 4% With tetraethylammonium perchlorate In methanol at 20℃; Electrochemical reaction;
Reference： [1]Blattes, Estelle; Fleury, Maurice-Bernard; Largeron, Martine [Journal of Organic Chemistry, 2004, vol. 69, # 3, p. 882 - 890]
  • 10
  • [ 6053-81-2 ]
  • [ 785796-47-6 ]
  • 8-[2-(cyclopentylmethyl-amino)-1-methyl-ethoxy]-quinolin-2-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With cyanoborane; acetic acid In methanol; 1,2-dichloro-ethane at 50℃; for 4h;
Reference： [1]Vasudevan, Anil; Wodka, Dariusz; Verzal, Mary K.; Souers, Andrew J.; Gao, Ju; Brodjian, Sevan; Fry, Dennis; Dayton, Brian; Marsh, Kennan C.; Hernandez, Lisa E.; Ogiela, Christopher A.; Collins, Christine A.; Kym, Philip R. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 19, p. 4879 - 4882]
  • 11
  • 4-dimethylamino-5-(dimethylaminomethyleneamino)thieno[8,9-b]pyridine-6-carboxylic acid methyl ester [ No CAS ]
  • [ 6053-81-2 ]
  • 3-Cyclopentylmethyl-9-dimethylamino-3H-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With toluene-4-sulfonic acid In toluene at 130℃;
Reference： [1]Zheng, Guo Zhu; Bhatia, Pramila; Daanen, Jerome; Kolasa, Teodozyj; Patel, Meena; Latshaw, Steven; El Kouhen, Odile F.; Chang, Renjie; Uchic, Marie E.; Miller, Loan; Nakane, Masaki; Lehto, Sonya G.; Honore, Marie P.; Moreland, Robert B.; Brioni, Jorge D.; Stewart, Andrew O. [Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7374 - 7388]
  • 12
  • [ 861102-81-0 ]
  • [ 6053-81-2 ]
  • 6-[(cyclopentylmethyl-amino)-methyl]-5-[4-(4-methanesulfonyl-benzylamino)-phenyl]-pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;
Reference： [1]Liu, Bo; Liu, Mei; Xin, Zhili; Zhao, Hongyu; Serby, Michael D.; Kosogof, Christi; Nelson, Lissa T.J.; Szczepankiewicz, Bruce G.; Kaszubska, Wiweka; Schaefer, Verlyn G.; Falls, H. Douglas; Lin, Chun Wel; Collins, Christine A.; Sham, Hing L.; Liu, Gang [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1864 - 1868]
  • 13
  • [ 675834-23-8 ]
  • [ 6053-81-2 ]
  • 2-(cyclopentylmethyl-amino)-<i>N</i>-(3-fluoro-2'-methanesulfonyl-biphenyl-4-yl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;
Reference： [1]Kohrt, Jeffrey T.; Filipski, Kevin J.; Cody, Wayne L.; Bigge, Christopher F.; La, Frances; Welch, Kathleen; Dahring, Tawny; Bryant, John W.; Leonard, Daniele; Bolton, Gary; Narasimhan, Lakshmi; Zhang, Erli; Peterson, J. Thomas; Haarer, Staci; Sahasrabudhe, Vaishali; Janiczek, Nancy; Desiraju, Shrilakshmi; Hena, Mostofa; Fiakpui, Charles; Saraswat, Neerja; Sharma, Raman; Sun, Shaoyi; Maiti, Samarendra N.; Leadley, Robert; Edmunds, Jeremy J. [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 13, p. 4379 - 4392]
  • 14
  • [ 911490-44-3 ]
  • [ 6053-81-2 ]
  • N-(cyclopentylmethyl)-3-[2-[3-(diethylamino)propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl] 4-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; 132 To the compound 3-[2-[3-(diethylamino)propyl]amino}-8-(2,6-difluorophenyl)-7- oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methylbenzoic acid (26 mg, 0.05 mmol) in DMF (0.5 mL) were added HBTU (28 mg, 0.075 mmol), triethylamine (21.1 uL, 0.15 mmol) and 1-cyclopentylmethanamine (9.9 mg, 0.1 mmol). The mixture was stirred at rt overnight. Separation by HPLC with TFA, afforded the title compound (10 mg, 33%). LC-MS m/z 603 (M+H)+.
Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2007/147103, 2007, A2 Location in patent: Page/Page column 195
  • 15
  • [ 6053-81-2 ]
  • 6-Chloro-9-cyclopentylmethyl-9H-purine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / butan-1-ol / 16 h / Heating 2: ethanesulfonic acid / 46 h / Ambient temperature
Reference： [1]Kelley, James L.; Morris Bullock; Krochmal, Mark P.; McLean, Ed W.; Linn, James A.; Durcan, Micheal J.; Cooper, Barrett R. [Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3207 - 3216]
  • 16
  • [ 6053-81-2 ]
  • (9-Cyclopentylmethyl-9H-purin-6-yl)-cyclopropyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Et3N / butan-1-ol / 16 h / Heating 2: ethanesulfonic acid / 46 h / Ambient temperature 3: 46 percent / Et3N / ethanol / 72 h / Ambient temperature
Reference： [1]Kelley, James L.; Morris Bullock; Krochmal, Mark P.; McLean, Ed W.; Linn, James A.; Durcan, Micheal J.; Cooper, Barrett R. [Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3207 - 3216]
  • 17
  • [ 6053-81-2 ]
  • Cyclopentylmethyl-carbamic acid 3-(1H-imidazol-4-yl)-propyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: charcoal / ethyl acetate / Heating 2: acetonitrile / Heating
Reference： [1]Stark, Holger; Purand, Katja; Ligneau, Xavier; Rouleau, Agnès; Arrang, Jean-Michel; Garbarg, Monique; Schwartz, Jean-Charles; Schunack, Walter [Journal of Medicinal Chemistry, 1996, vol. 39, # 5, p. 1157 - 1163]
  • 18
  • [ 6053-81-2 ]
  • [ 110707-74-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 73 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide, 4-(dimethylamino)pyridine / CH2Cl2 / 48 h / Ambient temperature 2: 30 percent / silver oxide / dioxane / 4 h / Heating
Multi-step reaction with 2 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h
Reference： [1]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[2]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 19
  • [ 6053-81-2 ]
  • [ 110707-80-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 73 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide, 4-(dimethylamino)pyridine / CH2Cl2 / 48 h / Ambient temperature 2: 30 percent / silver oxide / dioxane / 4 h / Heating 3: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 2 h 4: 87 percent / aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature
Multi-step reaction with 3 steps 1: 93 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 48 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 2 h 3: 87 percent / aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature
Multi-step reaction with 4 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to 25 deg C, 35 min, 2.) DMF, 25 deg C, 1 h 4: 89 percent / aq. LiOH / methanol; tetrahydrofuran
Reference： [1]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[2]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[3]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 20
  • [ 6053-81-2 ]
  • [ 110707-73-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 73 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide, 4-(dimethylamino)pyridine / CH2Cl2 / 48 h / Ambient temperature 2: 30 percent / silver oxide / dioxane / 4 h / Heating 3: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 2 h
Multi-step reaction with 2 steps 1: 93 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 48 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 2 h
Multi-step reaction with 3 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to 25 deg C, 35 min, 2.) DMF, 25 deg C, 1 h
Reference： [1]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[2]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[3]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 21
  • [ 6053-81-2 ]
  • [ 110707-84-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 73 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide, 4-(dimethylamino)pyridine / CH2Cl2 / 48 h / Ambient temperature 2: 30 percent / silver oxide / dioxane / 4 h / Heating 3: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 2 h 4: 87 percent / aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature 5: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 36 h / Ambient temperature
Multi-step reaction with 4 steps 1: 93 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 48 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 2 h 3: 87 percent / aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature 4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 36 h / Ambient temperature
Multi-step reaction with 5 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to 25 deg C, 35 min, 2.) DMF, 25 deg C, 1 h 4: 89 percent / aq. LiOH / methanol; tetrahydrofuran 5: 51 percent / Me2N(CH2)3N=C=NEt*HCl, DMAP / CH2Cl2
Reference： [1]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[2]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[3]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 22
  • [ 6053-81-2 ]
  • [ 145889-31-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 73 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide, 4-(dimethylamino)pyridine / CH2Cl2 / 48 h / Ambient temperature 2: 30 percent / silver oxide / dioxane / 4 h / Heating 3: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 18 h 4: aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature
Multi-step reaction with 3 steps 1: 93 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 48 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 18 h 3: aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature
Reference： [1]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[2]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
  • 23
  • [ 6053-81-2 ]
  • [ 145889-30-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 73 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide, 4-(dimethylamino)pyridine / CH2Cl2 / 48 h / Ambient temperature 2: 30 percent / silver oxide / dioxane / 4 h / Heating 3: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 18 h
Multi-step reaction with 2 steps 1: 93 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 48 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 18 h
Reference： [1]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[2]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
  • 24
  • [ 6053-81-2 ]
  • [ 145889-08-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 73 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide, 4-(dimethylamino)pyridine / CH2Cl2 / 48 h / Ambient temperature 2: 30 percent / silver oxide / dioxane / 4 h / Heating 3: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 18 h 4: aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature 5: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 36 h / Ambient temperature
Multi-step reaction with 4 steps 1: 93 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 48 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 18 h 3: aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature 4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 36 h / Ambient temperature
Reference： [1]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[2]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
  • 25
  • [ 6053-81-2 ]
  • 4-<<5-<(2-cyclopentylmethyl)carbamoyl>-1-propylindol-3-yl>methyl>-3-methoxy-N-<(2-methylphenyl)sulfonyl>benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 73 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide, 4-(dimethylamino)pyridine / CH2Cl2 / 48 h / Ambient temperature 2: 30 percent / silver oxide / dioxane / 4 h / Heating 3: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 18 h 4: aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature 5: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 36 h / Ambient temperature 6: 90 percent / 1N aq. NaOH, H2 / 10percent Pd/C / ethanol / 3 h / 2585.7 Torr
Multi-step reaction with 5 steps 1: 93 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 48 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 0 deg C, 0.5 h, 2.) DMF, RT, 18 h 3: aq. LiOH / tetrahydrofuran; methanol / 18 h / Ambient temperature 4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSCDI), 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 36 h / Ambient temperature 5: 90 percent / 1N aq. NaOH, H2 / 10percent Pd/C / ethanol / 3 h / 2585.7 Torr
Reference： [1]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
[2]Jacobs, Robert T.; Brown, Frederick J.; Cronk, Laura A.; Aharony, David; Buckner, Carl K.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 3, p. 394 - 409]
  • 26
  • [ 6053-81-2 ]
  • [ 104448-21-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) 1,1'-carbonyldiimidazole / 1.) CH2Cl2, reflux, 30 min, 2.) CH2Cl2, reflux, 30 min 2: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) DMF, RT, 24 h 3: 50 percent / aq. LiOH / methanol; tetrahydrofuran
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 27
  • [ 6053-81-2 ]
  • [ 110707-82-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to 25 deg C, 35 min, 2.) DMF, 25 deg C, 1 h 4: 1.) ozone, 2.) Me2S / 1.) CH2Cl2, MeOH, -78 deg C, 15 min, 2.) CH2Cl2, MeOH, from -78 deg C to RT 5: 66 percent / hydroxylamine hydrochloride, pyridine / 1.5 h / 120 °C 6: 79 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 8 h 7: 93 percent / 0.08 h / 200 °C / 0.1 Torr 8: 87 percent / aq. LiOH / methanol; tetrahydrofuran
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 28
  • [ 6053-81-2 ]
  • [ 110707-76-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to 25 deg C, 35 min, 2.) DMF, 25 deg C, 1 h 4: 1.) ozone, 2.) Me2S / 1.) CH2Cl2, MeOH, -78 deg C, 15 min, 2.) CH2Cl2, MeOH, from -78 deg C to RT 5: 66 percent / hydroxylamine hydrochloride, pyridine / 1.5 h / 120 °C 6: 79 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 8 h 7: 93 percent / 0.08 h / 200 °C / 0.1 Torr
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 29
  • [ 6053-81-2 ]
  • [ 110707-78-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to 25 deg C, 35 min, 2.) DMF, 25 deg C, 1 h 4: 1.) ozone, 2.) Me2S / 1.) CH2Cl2, MeOH, -78 deg C, 15 min, 2.) CH2Cl2, MeOH, from -78 deg C to RT
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 30
  • [ 6053-81-2 ]
  • [ 110707-79-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to 25 deg C, 35 min, 2.) DMF, 25 deg C, 1 h 4: 1.) ozone, 2.) Me2S / 1.) CH2Cl2, MeOH, -78 deg C, 15 min, 2.) CH2Cl2, MeOH, from -78 deg C to RT 5: 66 percent / hydroxylamine hydrochloride, pyridine / 1.5 h / 120 °C
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 31
  • [ 6053-81-2 ]
  • [ 104448-73-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) 1,1'-carbonyldiimidazole / 1.) CH2Cl2, reflux, 30 min, 2.) CH2Cl2, reflux, 30 min 2: 1.) NaH / 1.) DMF, 0 deg C, 1 h, 2.) DMF, RT, 24 h 3: 50 percent / aq. LiOH / methanol; tetrahydrofuran 4: 63 percent / Me2N(CH2)3N=C=NEt*HCl, DMAP / CH2Cl2
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 32
  • [ 6053-81-2 ]
  • [ 110707-77-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to 25 deg C, 35 min, 2.) DMF, 25 deg C, 1 h 4: 1.) ozone, 2.) Me2S / 1.) CH2Cl2, MeOH, -78 deg C, 15 min, 2.) CH2Cl2, MeOH, from -78 deg C to RT 5: 66 percent / hydroxylamine hydrochloride, pyridine / 1.5 h / 120 °C 6: 79 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 8 h
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 33
  • [ 6053-81-2 ]
  • [ 142535-33-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to RT, 35 min, 2.) DMF, RT, 15 min 4: 59 percent / aq. LiOH / methanol; tetrahydrofuran
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 34
  • [ 6053-81-2 ]
  • [ 142563-82-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to RT, 35 min, 2.) DMF, RT, 15 min
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 35
  • [ 6053-81-2 ]
  • [ 142535-36-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, 8 h 4: 80 percent / aq. LiOH / methanol; tetrahydrofuran
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 36
  • [ 6053-81-2 ]
  • [ 142535-35-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, 8 h
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 37
  • [ 6053-81-2 ]
  • [ 142535-26-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to 25 deg C, 35 min, 2.) DMF, 25 deg C, 1 h 4: 1.) ozone, 2.) Me2S / 1.) CH2Cl2, MeOH, -78 deg C, 15 min, 2.) CH2Cl2, MeOH, from -78 deg C to RT 5: 66 percent / hydroxylamine hydrochloride, pyridine / 1.5 h / 120 °C 6: 79 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 8 h 7: 93 percent / 0.08 h / 200 °C / 0.1 Torr 8: 87 percent / aq. LiOH / methanol; tetrahydrofuran 9: 64 percent / Me2N(CH2)3N=C=NEt*HCl, DMAP / CH2Cl2
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 38
  • [ 6053-81-2 ]
  • [ 142535-34-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, from 0 deg C to RT, 35 min, 2.) DMF, RT, 15 min 4: 59 percent / aq. LiOH / methanol; tetrahydrofuran 5: 68 percent / Me2N(CH2)3N=C=NEt*HCl, DMAP / CH2Cl2
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 39
  • [ 6053-81-2 ]
  • [ 142535-37-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 12 h 2: 1.) Ag2O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h 3: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, 8 h 4: 80 percent / aq. LiOH / methanol; tetrahydrofuran 5: 55 percent / Me2N(CH2)3N=C=NEt*HCl, DMAP / CH2Cl2
Reference： [1]Brown; Cronk; Aharony; Snyder [Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439]
  • 40
  • [ 727383-04-2 ]
  • [ 6053-81-2 ]
  • ethyl 5-{2-[2-(cyclopentyl)methylamino-pyridin-4-yl]-thiazol-4-yl}-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper In 2,4,6-trimethyl-pyridine at 160℃; for 16h; 62 Example 62; Ethyl 5-{2-[2-(Cyclopentyl)methylamino-pyridin-4-yl]-thiazol-4-yl}-2-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate A mixture of ethyl 5-(2-(2-chloro-4-pyridinyl)-1,3-thiazol-4-yl)-2-methyl-6-oxo-1,6-dihydro-3-pyridine-carboxylate (Example 40) (0.10 g, 0.27 mmol), cyclopentyl-methylamine (0.07 g, 0.54 mmol), and Cu powder (0.09 g, 0.14 mmol) in 2,4,6-collidine (3 ML) was heated at 160° C. for 16 h.The mixture was cooled, concentrated, and purified by flash column chromatography (5% MeOH/CH2Cl2) to give a light yellow solid.The solid was dissolved in warm 1,4-dioxane and treated with 1 M HCl in ether.The HCl salt was filtered and dried by air. MS (M+1): 439.1. Calc'd for C23H26N4O3S Exact Mass: 438.17. MP: 260° C. (dec).
Reference： [1]Current Patent Assignee: AMGEN INC - US2004/147561, 2004, A1 Location in patent: Page 55
  • 41
  • [ 675618-02-7 ]
  • [ 6053-81-2 ]
  • [ 675618-05-0 ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one at 180℃; for 14h; 219 [EXAMPLE 219] N-(cyclopentanemethyl)- 4-(trifluoromethyl)-6-[4-(methylsulfonyl)phenyl]pyridine- 2-amine [EXAMPLE 219] N-(cyclopentanemethyl)- 4-(trifluoromethyl)-6-[4-(methylsulfonyl)phenyl]pyridine- 2-amine A stirred solution of intermediate 9 (630mg, 1. 9mmol) and cyclopentanemethylamine (373mg, 3. [8MMOL)] in NMP (5mL) was heated at [180°C] for 14 hours. After cooling, the reaction was diluted with water [(150ML)] and filtered to give the title product (582mg) LC retention time 3.80mins MS m/z 399 (MH+) [; H-NMR (CDCIS) 8] 1.27-1. 38 (2H, m), 1.52-1. 74 (4H, m), 1.82-1. 92 (2H, m) 2.23 (1H, hept, J = 7Hz), 3.10 (3H, s), 3.33 (2H, dd, J = 7Hz & 6Hz), 4.95 (1H, t, J = 6Hz), 6.60 (1H, s), 7.22 (1H, s), 8.03 (2H, d, J = 8Hz), 8.19 (2H, d, J = 8Hz).
Reference： [1]Current Patent Assignee: SWARBRICK; PEGG; SKIDMORE (inventors); BESWICK, PAUL; GLAXOSMITHKLINE PLC; EFG INTERNATIONAL AG - WO2004/24691, 2004, A1 Location in patent: Page 41
  • 42
  • [ 51598-76-6 ]
  • [ 6053-81-2 ]
  • N-(cyclopentylmethyl)-6-methylnicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane for 4h; 96 N-(cyclopentylmethyl)-6-methylnicotinamide EXAMPLE 96 N-(cyclopentylmethyl)-6-methylnicotinamide A suspension of 6-methylnicotinic acid (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0° C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of cyclopentylmethylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 219.2 (M+H)+; 1H NMR (DMSO-d6) δ 1.20-1.31 (m, 2H), 1.45-1.64 (m, 4H), 1.64-1.74 (m, 2H), 2.09-2.19 (m, 1H), 2.59 (s, 3H), 3.18-3.24 (m, 2H), 7.55 (d, 1H), 8.29 (dd, 1H), 8.67 (t, 1H), 8.95 (d, 1H).
Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - US2004/67985, 2004, A1 Location in patent: Page/Page column 20-21
  • 43
  • [ 849350-75-0 ]
  • [ 6053-81-2 ]
  • N-{4-[(cyclopentylmethyl)amino]-3-nitrophenyl}-N-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine In ethanol at 75℃; for 5h; 55.B Step B : N-{4-[(CYCLOPENTYLMETHYL) AMINO]-3-NITROPHENYL}-N- methylbenzenesulfonamide; N-(4-FLUORO-3-NITROPHENYL)-N-METHYLBENZENESULFONAMIDE (for preparation see Example 3, Steps B and C) (50 mg, 0.161 mmol) and cyclopentylmethylamine (0.062 mL of a 1g/3 mL solution, 0.209 mmol) were stirred in 2 mL OF ETOH containing TEA (0.025 mL, 0.241 mmol) at 75°C for 5h. The solvent was evaporated. The residue was dissolved in EtOAc and washed with 5% aqueous KHSO4 solution, aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The crude product was purified by silica gel flash chromatography using 3: 1/hexanes: EtOAc as eluent. Yield: 57 mg (91%).'H NMR (400 MHz, CHLOROFORM-D): No. 1.31 (m, 3 H), 1.66 (m, 4 H), 1.91 (m, 2 H), 2. 28 (m, 1 H), 3.13 (s, 3 H), 3.24 (dd, J=7.23, 5. 08 Hz, 2 H), 6. 84 (d, J=9. 37 Hz, 1 H), 7.45 (dd, J=9. 28, 2.64 Hz, 1 H), 7. 50 (m, 2 H), 7.60 (m, 3H), 8. 17 (M, 1 H).
91% With triethylamine In ethanol at 75℃; for 5h; 35.B Step B: N-44-[(CYCLOPENTYLMETHYL) AMINOL-3-NITROPHENYL}-N- methylbenzenesulfonamide; N- (4-FLUORO-3-NITROPHENYL)-N-METHYLBENZENESULFONAMIDE (for preparation see Example 3, Steps B and C) (50 mg, 0.161 mmol) and cyclopentylmethylamine (0.062 MOL of a lg/3 mL solution, 0.209 mmol) were stirred in 2 ML OF ETOH containing TEA (0.025 mL, 0.241 mmol) at 75°C for 5h. The solvent was evaporated. The residue was dissolved in EtOAc and washed with 5% aqueous KHS04 solution, aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The crude product was purified by silica gel flash chromatography using 3: 1/hexanes : EtOAc as eluent. Yield: 57 mg (91%). 1H NMR (400 MHz, CHLOROFORM-D): 8 1.31 (m, 3 H), 1.66 (m, 4 H), 1.91 (m, 2 H), 2.28 (m, 1 H), 3.13 (s, 3 H), 3.24 (dd, J=7.23, 5.08 Hz, 2 H), 6.84 (d, J=9. 37 Hz, 1 H), 7.45 (dd, J=9.28, 2.64 Hz, 1 H), 7.50 (m, 2 H), 7.60 (m, 3 H), 8.17 (m, 1 H).
With triethylamine In ethanol Reflux;
Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2005/30761, 2005, A1 Location in patent: Page/Page column 98-99
[2]Current Patent Assignee: ASTRAZENECA PLC - WO2005/30762, 2005, A1 Location in patent: Page/Page column 66-67
[3]Location in patent: scheme or table Page, Daniel; Wei, Zhongyong; Liu, Ziping; Tremblay, Maxime; Desfosses, Helene; Milburn, Claire; Srivastava, Sanjay; Yang, Hua; Brown, William; Walpole, Christopher; Tomaszewski, Mirek; St-Onge, Stephane; Lessard, Etienne; Payza, Kemal; Panetta, Rosemarie; Yu, Xiao Hong; Groblewski, Thierry [Letters in drug design and discovery, 2010, vol. 7, # 3, p. 208 - 213]
  • 44
  • [ 690266-28-5 ]
  • [ 6053-81-2 ]
  • (2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-cyclopentylmethyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 60℃; for 20h; 1.19a 1.19a (2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-cyclopentylmethyl-amine A mixture of 1.33 g (3.0 mmol) methanesulphonate 2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl, 595 mg (6.0 mmol) cyclopentyl-methylamine and 2.57 mL (15.0 mmol) N-ethyldiisopropylamine in 30 mL DMF is stirred for 20 h at 60° C. It is evaporated down i. vac., the residue is taken up in semiconcentrated K2CO3 solution, the organic phase is separated off and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, DCM/MeOH 95:5). Yield: 0.57 g (42% of theoretical) C28H29ClN2O (M=444.995)
42% With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 60℃; for 20h;
Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2005/239826, 2005, A1 Location in patent: Page/Page column 33
[2]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2005/103031, 2005, A1 Location in patent: Page/Page column 79-80
  • 45
  • [ 6053-81-2 ]
  • [ 501-53-1 ]
  • [ 172738-63-5 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate 29.A Example 29 A. Benzyl chloroformate (0.919 g, 5.38 mmol) was added to a solution of cyclopentylmethylamine (0.445 g, 4.49 mmol) and DIEA (1.74 g, 13.5 mmol) in 50 mL of CH2 Cl2 and the mixture was strried overnight at R.T. The mixture was concentrated in vacuo and the residue was taken up in EtOAc, washed with water, sat. aq. NaHCO3, brine, dried over MgSO4 and concentrated to give the crude N-Cbz-cyclopentylmethylamine (1.275 g) which was used without further purification. 1 H NMR consistent with structure.
Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US6127372, 2000, A
  • 46
  • (2RS,3S)-2-hydroxy-3-[N-[1-[N-(4-acetylpiperazine-1-carbonyl) amino]cyclohexanecarbonyl]amino]heptanoic acid [ No CAS ]
  • [ 6053-81-2 ]
  • [ 274684-91-2 ]
YieldReaction ConditionsOperation in experiment
11% 66 Synthesis of N-[(S)-1-(N-cyclopentylmethylamino)-1,2-dioxo-3-heptyl]-1-[N-(4-acetylpiperazine-1-carbonyl)amino]cyclohexanecarboxamide STR99 Example 66 Synthesis of N-[(S)-1-(N-cyclopentylmethylamino)-1,2-dioxo-3-heptyl]-1-[N-(4-acetylpiperazine-1-carbonyl)amino]cyclohexanecarboxamide STR99 The same procedure as in Example 28 was repeated except that the (2RS,3S)-2-hydroxy-3-[1-[N-[N-(morpholine-4-carbonyl)amino]cyclohexanecarbonyl]amino]heptanoic acid was replaced by 881 mg of (2RS,3S)-2-hydroxy-3-[N-[1-[N-(4-acetylpiperazine-1-carbonyl)amino]cyclohexanecarbonyl]amino]heptanoic acid synthesised in Reference Example 28 and the 3-chlorobenzylamine was replaced by 496 mg of cyclopentylmethylamine, whereby 64 mg of the captioned N-[(S)-1-(N-cyclopentylmethylamino)-1,2-dioxo-3-heptyl]-1-[N-(4-acetylpiperazine-1-carbonyl) amino]cyclohexanecarboxamide was obtained in a yield of 11%. 1H-NMR (CDCl3, δ): 0.86-0.90 (3H, m), 1.17-1.44 (9H, m), 1.53-1.77 (8H, m), 1.86-2.14 (10H, m), 3.22 (2H, dd, J=6 Hz, 7 Hz), 3.34-3.41 (2H, m), 3.45-3.51 (5H, m), 3.67-3.70 (2H, m), 4.52 (1H, s), 5.17-5.22 (1H, m), 6.90 (1H, t, J=6 Hz), 7.79 (1H, d, J=7 Hz) IR (ν, KBr, cm-1): 3353, 2952, 1629, 1529, 1444, 1250
Reference： [1]Current Patent Assignee: SEIKAGAKU CORPORATION - US6117870, 2000, A
  • 47
  • [ 67-36-7 ]
  • [ 6053-81-2 ]
  • N-(cyclopentylmethyl)-N-(4-phenoxybenzyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.4 g (80%) With sodium cyanoborohydride In methanol; dichloromethane 101.A N-Cyclopentylmethyl-N-(4-phenoxybenzyl)amine EXAMPLE 101A N-Cyclopentylmethyl-N-(4-phenoxybenzyl)amine 4-Phenoxybenzaldehyde (3.0 g, 15.1 mmol) and cyclopentylmethylamine (1.49 g, 15.1 mmol) were dissolved in methanol (85 mL) under nitrogen at room temperature. Sodium cyanoborohydride (0.95 g, 15.1 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated, and the residue was suspended in ether, washed with brine, and dried over Na2 SO4. The ether was evaporated, and the crude product was chromatographed on silica gel eluding with 3% methanol in methylene chloride to provide 3.4 g (80%) of the title compound as a colorless oil. 1 H NMR (CDCl3, 300 MHz) δ 1.10-1.24 (m, 2H), 1.45-1.67 (m, 2H), 1.71-1.90 (m, 3H), 2.06 (p, J=7.5 Hz, 1H), 2.58 (d, J=7.5 Hz, 2H), 3.79 (s, 2H), 6.95-7.05 (m, 4H) 7.09 (tt, J=7.5, 1.5 Hz, 1H), 7.28-7.38 (m, 4H). MS (DCl/NH3) m/e 282 (M+H)+.
Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - US5631401, 1997, A
  • 48
  • [ 6053-81-2 ]
  • [ 76-05-1 ]
  • N-(cyclopentylmethyl)-3-[2-[3-(diethylamino)propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methylbenzamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% Stage #1: 3-[2-[3-(diethylamino)propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methylbenzoic acid; cyclopentylmethylamine With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; Stage #2: trifluoroacetic acid In N,N-dimethyl-formamide 132 Example 132; iy-(cvclopentylmethyl)-3-r2-(f3-(diethylamino)propyllamino)-8-r2.6- difluorophenylV7-oxo-7,8-dihydropyrido[2,3-+.
Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2006/104915, 2006, A2 Location in patent: Page/Page column 218
  • 49
  • 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride [ No CAS ]
  • [ 6053-81-2 ]
  • N-Cyclopentylmethyl 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; sodium hydrogencarbonate In dichloromethane; acetonitrile 92 EXAMPLE 92 EXAMPLE 92 Thionyl chloride (2 cc) is added to a suspension, cooled to 5° C., of 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxylic acid hydrochloride (1.6 g) in methylene chloride (50 cc). The suspension is stirred for 3 hours at 15° C. and then concentrated to dryness at 30° C. under reduced pressure (30 mm Hg; 4 kPa) to give a yellow residue which is taken up in methylene chloride (50 cc) at 5° C. Cyclopentylmethylamine (1.1 g) is added and the mixture is stirred for 12 hours at 25° C., and saturated sodium bicarbonate solution (150 cc) is then added. The mixture is extracted with ethyl acetate (2*100 cc). The organic phase is washed successively with distilled water (100 cc) and with brine (100 cc), dried over magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (30 mm Hg; 4 kPa). The yellow solid obtained (1.6 g) is dissolved in boiling acetonitrile (30 cc) and the solution is filtered. The filtrate is primed by scratching and then cooled with stirring for 1 hour. The solid is separated off by filtration, washed with acetonitrile (2*2 cc) and dried at 40° C. under reduced pressure (1 mm Hg; 0.13 kPa). N-Cyclopentylmethyl 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide (1.3 g) is obtained in the form of white crystals, m.p. 124° C. 1 Proton NMR (250 MHz, CDCl3, δ in ppm, J in Hz) 1.28, 1.64 and 1.83 (3 Mt, 2H-4H and 2H respectively, cyclopentyl --CH2 --); 1.7 (D, J=7, 3H, --CH3); 1.84 (Mt, 4H, pyrrolidine --CH2 --CH2 --); 2.18 (Mt, 1H, cyclopentyl --CH--); 2.74 (Mt, 4H, pyrrolidine STR34 3.02 (DD, J=13.5 and 6, 1H, 1H of >N--CH2 --); 3.23 (DD, J=13.5 and 6.5, 1H, 1H of >N--CH2 --); 3.4 (DD, J=7 and 5.5, 2H, --CONH--CH2 --); 4.4 (Mt, J=7, 6.5 and 6, 1H, >N--CH
Reference： [1]Current Patent Assignee: DANFOSS A/S; SANOFI - US4985419, 1991, A
  • 50
  • [ 6053-81-2 ]
  • [ 39689-58-2 ]
  • [ 530-62-1 ]
  • [ 119160-62-2 ]
YieldReaction ConditionsOperation in experiment
81% In dichloromethane; N,N-dimethyl-formamide; h. N-Cyclopentylmethylindole-6-acetamide A solution of <strong>[39689-58-2]indole-6-acetic acid</strong> (0.70 g) and 1,1'-carbonyldiimidazole (0.83 g) in methylene chloride (20 ml) and N,N-dimethylformamide (5 ml) was heated at reflux for 20 min, treated with cyclopentylmethylamine (0.59 g), and heated at reflux for an additional 3 hr. The solution was diluted with methylene chloride; washed successively with 10% v/v hydrochloric acid, water and brine; dried (MgSO4); and evaporated. The residue was purified by flash chromatography, eluding with 1:19 ethyl acetate: hexane, to give N-cyclopentylmethylindole-6-acetamide (0.83, 81%) as a white powder; partial NMR (80 MHz, CDCl3): 3.13(t, 2H, NHCH2), 3.69(s, 2H, ArCH2), 6.55(m, 1H, H3 -indole), 6.98(dd, 1H, H5 -indole), 7.62(d, 1H, H4 -indole).
Reference： [1]Patent: US4894386,1990,A
  • 51
  • [ 1670-82-2 ]
  • [ 6053-81-2 ]
  • [ 530-62-1 ]
  • [ 104447-78-1 ]
YieldReaction ConditionsOperation in experiment
91% In dichloromethane; (d) A solution of <strong>[1670-82-2]indole-6-carboxylic acid</strong> (9.41 g) and 1,1'carbonyldiimidazole (10.6 g) in methylene chloride (290 ml) was heated at reflux, under nitrogen, for 30 minutes. The solution was cooled and treated with cyclopentylmethylamine (7.0 g). This mixture was heated to reflux for 30 minutes. The resultant solution was then diluted with methylene chloride, washed successively with 10% (v/v) hydrochloric acid, 20% (w/v) aqueous sodium hydroxide, and brine, dried (MgSO4), and evaporated to give 6-(N-cyclopentylmethylcarbamoyl)indole (14.4 g, 91%) as an ivory powder, mp 148-150; NMR (80 MHz, DMSO-d6): 3.19(dd, 2H, CH2 NH), 6.46(br d, 1H, H3 -indole), 7.91(d, 1H, H7 -indole), 8.29(t, 1H, CH2 NH).
91% In dichloromethane; (d) A solution of <strong>[1670-82-2]indole-6-carboxylic acid</strong> (9.41 g) and 1,1'-carbonyldiimidazole (10.6 g) in methylene chloride (290 ml) was heated at reflux, under nitrogen, for 30 minutes. The solution was cooled and treated with cyclopentylmethylamine (7.0 g). This mixture was heated to reflux for 30 minutes. The resultant solution was then diluted with methylene chloride, washed successively with 10% (v/v) hydrochloric acid, 20% (w/v) aqueous sodium hydroxide, and brine, dried (MgSO4), and evaporated to give 6-(N-cyclopentylmethylcarbamoyl)indole (14.4 g, 91%) as an ivory powder, mp 148-150; NMR (80 MHz, DMSO-d6): 3.19(dd, 2H, C H 2NH), 6.46(br d, 1H, H3-indole), 7.91(d, 1H, H7-indole), 8.29(t, 1H, CH2N H).
Reference： [1]Patent: US4898863,1990,A
[2]Patent: EP242167,1991,B1
  • 52
  • 10,11-bis-[2-(methylsulphonyloxy)-ethyl]-5H-dibenzo[a,d]cycloheptene [ No CAS ]
  • [ 6053-81-2 ]
  • [ 7087-68-5 ]
  • 3-(cyclopentylmethyl)-1,2,3,4,5,10-hexahydro-dibenzo[3,4:6,7]cyclohepta[1,2-d]azepine methanesulphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; conc. ammonia In sodium hydroxide; ethanol; hexane; dichloromethane; water; pentane 3 EXAMPLE 3 EXAMPLE 3 To a solution of 43.6 g (0.1 mole) of 10,11-bis-[2-(methylsulphonyloxy)-ethyl]-5H-dibenzo[a,d]cycloheptane in 400 ml of absolute ethanol are added 11.9 g (0.12 mole) of (aminomethyl)-cyclopentane and 32.3 g (0.25 mole) of diisopropyl ethylamine. The reaction mixture is then concentrated in a water jet vacuum, the residue dissolved in 150 ml of methylene chloride and 500 ml of pentane, and the solution washed in succession with 200 ml of 2N sodium hydroxide solution and 200 ml of water. The organic phase is subsequently treated with 200 ml of 2N hydrochloric acid and the hydrochloride precipitates in crystals. The crystals are collected with suction and the base is set free by suspending the hydrochloride in 300 ml of methylene chloride and extraction with 100 ml of conc. ammonia solution. The methylene chloride solution is separated and concentrated until the onset of crystallisation. After the addition of hexane, the 3-(cyclopentyl-methyl)-1,2,3,4,5,10-hexahydro-dibenzo[3,4:6,7]cyclohepta[1,2-d]azepine with a melting point of 141°-142° C. crystallises out. For conversion into the methanesulphonate, the base is dissolved in methylene chloride, the solution is acidified with the theoretical amount of methanesulphonic acid, and the 3-(cyclopentylmethyl)-1,2,3,4,5,10-hexahydro-dibenzo[3,4:6,7]cyclohepta[1,2-d]azepine methanesulphonate is precipitated with ether. Melting point: 248°-249° C.
Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US4707476, 1987, A
  • 53
  • 2-bromo-10,11-bis-[2-(methylsulphonyloxy)ethyl]-dibenz[b,f]oxepin [ No CAS ]
  • [ 6053-81-2 ]
  • 3-(cyclopentylmethyl)-7-cyano-2,3,4,5-tetrahydro-1H-dibenz[2,3:6,7]oxepino[4,5-d]azepine [ No CAS ]
  • [ 79262-42-3 ]
YieldReaction ConditionsOperation in experiment
In ethanol; acetonitrile 2 EXAMPLE 2 The starting material, 7-bromo-3-(cyclopentylmethyl)-2,3,4,5-tetrahydro-1H-dibenz[2,3:6,7]oxepino[4,5-d]azepine, is prepared from 51.7 g (0.01 mol) of crude 2-bromo-10,11-bis-[2-(methylsulphonyloxy)ethyl]-dibenz[b,f]oxepin and 29.7 g (0.3 mol) of (aminomethyl)cyclopentane in 100 ml of ethanol in a manner analogous to that of the last section of Example 1. Melting point 125° to 128° (from acetonitrile).
Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US4492691, 1985, A
  • 54
  • [ 59814-20-9 ]
  • [ 6053-81-2 ]
  • [ 59815-58-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethanol; water 76 4-(4-Chloro-3-cyclopentylmethylsulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol EXAMPLE 76 4-(4-Chloro-3-cyclopentylmethylsulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol 8.8 g of 4-(4-chloro-3-chlorosulfonylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrobromide were introduced portionswise at 20° C in a stirred mixture of 4 g of cyclopentylmethyl amine, 8 g of triethyl amine and 100 ml of ethanol and the reaction mixture was allowed to stand over night. The solvent was distilled off under reduced pressure and the amorphous end product was crystallized under 80 ml of water. Colorless solid body, decomposition beginning at 80° C, γ C=N 1620 cm-1.
Reference： [1]Current Patent Assignee: SANOFI - US4061761, 1977, A
  • 55
  • t-butyloxycarbonyl anhydride [ No CAS ]
  • sodium cyanoborohydride (NaBH3CN) [ No CAS ]
  • [ 120-92-3 ]
  • [ 6053-81-2 ]
YieldReaction ConditionsOperation in experiment
90.5% With hydrogenchloride; sodium hydroxide; methylamine hydrochloride In 1,4-dioxane; methanol; HCl-dioxane; water 1 Synthesis of cyclopentyl-methylamine Preparation 1 Synthesis of cyclopentyl-methylamine To a solution of cyclopentanone(10ml, 113 mmol) in methanol (50ml) and water(50ml) were added methylamine hydrochloride(7.6g, 113 mmol) and sodium cyanoborohydride (NaBH3CN) (7.1g, 113 mmol). The mixture was heated to reflux for 12hrs at pH 6. Methanol was evaporated under reduced pressure and the residue was cooled to 0°C, adjusted to pH 2 using 3N hydrochloric acid and then washed three times with diethyl ether. The aqueous layer was cooled again to 0°C and then adjusted to pH 11 using 6N sodium hydroxide solution. To this mixture was added t-butyloxycarbonyl anhydride (24.5g, 113 mmol) in dioxane(50 ml). The solution was stirred for 3 hours at room temperature and concentrated under reduced pressure to about 30ml. The residue was extracted with ethyl acetate and washed with aqueous 0.5N hydrochloric acid and saturated sodium bicarbonate solutions. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the white solid which was then purified by column chromatography(eluent = ethyl acetate:hexane = 7:3 (v/v)). Upon purification, the obtained solid product was dissolved in 4N HCl-dioxane solution(60ml) and the resulting solution was stirred for 30 minutes at room temperature. The solvent was evaporated in vacuo to obtain the title compound (13.7g Yield:90.5%).
Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - EP739886, 1996, A2
  • 56
  • [ 935527-17-6 ]
  • [ 6053-81-2 ]
  • N-cyclopentylmethyl-3,5-dimethoxy-4-(2-propynyloxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran at 20℃; for 1h; 29 Production Example 29; To a mixture of 5 ml of THF and 0.30 g of 3,5- dimethoxy-4- (2-propynyloxy) benzoyl chloride were added 0.15 g of 1- (cyclopentyl) methylamine and 0.21 g of triethylamine in order at room temperature. The mixture obtained was stirred at room temperature for 1 hour. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.13 g of N- cyclopentylmethyl-3, 5-dimethoxy- (2-propynyloxy) benzamide (hereinafter, described as the compound 30 of the present invention) represented by the formula: The compound 30 of the present invention:1H-NMR (CDCl3) δ: 1.21-1.34 (2H, m) , 1.51-1.72 (4H, m) ,1.73-1.87 (2H, m) , 2.10-2.24 (IH, m) , 2.43 (IH, t, J = 2.4Hz), 3.39 (2H, dd, J = 7.4, 5.9 Hz), 3.90 (6H, s) , 4.77 (2H, d, J = 2.4 Hz), 6.10 (IH, br s) , 6.98 (2H, s) .
Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - WO2007/49728, 2007, A1 Location in patent: Page/Page column 88-89
  • 57
  • [ 935527-19-8 ]
  • [ 6053-81-2 ]
  • N-cyclopentylmethyl-4-(2-propynyloxy)-3-methoxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran at 0 - 20℃; for 4h; 11 Production Example 11; To a mixture of 10 ml of• THF and 0.3 g of 3-methoxy-4- (2-propynyloxy) benzoyl chloride were added dropwise 0.15 g of cyclopentylmethylamine and 0.16 g of triethylamine in order under ice cooling. The mixture obtained was stirred at room temperature for 4 hours. Then, ethyl acetate was added to the reaction mixture and it was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.31 g of N-cyclopentylmethyl-4- (2-propynyloxy) -3-methoxybenzamide (hereinafter, described as the compound 11 of the present invention) represented by the formula:The compound 11 of the present invention: 1H-NMR (CDCl3) δ: 1.21-1.32 (2H, m) , 1.50-1.85 (6H, m) , 2.09-2.22 (IH, m) , 2.53 (IH, t, J = 2.3 Hz), 3.38 (2H, dd, J = 7.1, 5.9 Hz), 3.92 (3H, s) , 4.80 (2H, d, J = 2.4 Hz), 6.20 (IH, br s) , 7.02 (IH, d, J = 8.3 Hz), 7.25 (IH, dd, J = 8.3, 2.0 Hz), 7.46 (IH, d, J = 2.0 Hz).
Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - WO2007/49728, 2007, A1 Location in patent: Page/Page column 73-74
  • 58
  • [ 935527-28-9 ]
  • [ 6053-81-2 ]
  • N-cyclopentylmethyl-3,5-difluoro-4-(2-propynyloxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethyl acetate at 20℃; for 12h; 56 Production Example 56; A mixture of 0.50 g of cyclopentylmethylamine, 0.4 ml of triethylamine and 2 ml of ethyl acetate was added dropwise under ice cooling to a mixture of 3 ml of ethyl acetate and 0.46 g of 3, 5-difluoro-4- (2-propynyloxy) benzyl chloride. The mixture obtained was stirred at room temperature for 12 hours. Then, the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.24 g of N-cyclopentylmethyl-3, 5-difluoro-4- (2- propynyloxy) benzamide (hereinafter, described as the compound 58 of the present invention) represented by the formula:The compound 58 of the present invention: 1H-NMR (CDCl3) δ: 1.21-1.84 (8H, m) , 2.10-2.18 (IH, m) ,2.52 (IH, t, J = 2.4 Hz), 3.37 (2H, dd, J = 7.2, 5.8 Hz),4.87 (2H, d, J = 2.4 Hz), 6.11 (IH, br s) , 7.31-7.38 (2H, m) .
Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - WO2007/49728, 2007, A1 Location in patent: Page/Page column 109-110
  • 59
  • [ 3222-47-7 ]
  • [ 6053-81-2 ]
  • N-(cyclopentylmethyl)-6-methylnicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; triethylamine; trifluoroacetic acid In dichloromethane; water; acetonitrile 96 N-(cyclopentylmethyl)-6-methylnicotinamide EXAMPLE 96 N-(cyclopentylmethyl)-6-methylnicotinamide A suspension of 6-methylnicotinic acid (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0° C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of cyclopentylmethylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), l0 filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 219.2 (M+H)+; 1H NMR (DMSO-d6) δ 1.20-1.31 (m, 2H), 1.45-1.64 (m, 4H), 1.64-1.74 (m, 2H), 2.09-2.19 (m, 1H), 2.59 (s, 3H), 3.18-3.24 (m, 2H), 7.55 (d, 1H), 8.29 (dd, 1H), 8.67 (t, 1H), 8.95 (d, 1H).
Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - US2004/116479, 2004, A1
  • 60
  • [ 1018481-30-5 ]
  • [ 6053-81-2 ]
  • [ 1018480-53-9 ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine
Reference： [1]Orjales, Aurelio; Mosquera, Ramon; Lopez, Beatriz; Olivera, Roberto; Labeaga, Luis; Nunez, M. Teresa [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2183 - 2199]
  • 61
  • [ 1050494-43-3 ]
  • [ 6053-81-2 ]
  • C17H26N6O [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 170℃; for 0.0333333h; Microwave irradiation; Intermediate 105: 8-Bromo-/V2-(cvclopentylmethyl)-9-(tetrahvdro-2H-pyran-4- ylmethyl)-9H-purine-2,6-diamine A solution of 2-chloro-9-(tetrahydro-2/-/-pyran-4-ylmethyl)-9/-/-purin-6-amine (150 mg) in cyclopentylamine (276 mg) was heated in the microwave at 1700C for two minutes. The reaction mixture was concentrated in vacuo.
Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2008/101867, 2008, A1 Location in patent: Page/Page column 105-106
  • 62
  • [ 474018-94-5 ]
  • [ 6053-81-2 ]
  • [ 909706-24-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethanol at 75℃;
Reference： [1]Location in patent: scheme or table Pagé, Daniel; Balaux, Elise; Boisvert, Luc; Liu, Ziping; Milburn, Claire; Tremblay, Maxime; Wei, Zhongyong; Woo, Simon; Luo, Xuehong; Cheng, Yun-Xing; Yang, Hua; Srivastava, Sanjay; Zhou, Fei; Brown, William; Tomaszewski, Miroslaw; Walpole, Christopher; Hodzic, Leila; St-Onge, Stéphane; Godbout, Claude; Salois, Dominic; Payza, Keymal [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 13, p. 3695 - 3700]
  • 63
  • [ 1089672-86-5 ]
  • [ 6053-81-2 ]
  • [ 1089672-67-2 ]
YieldReaction ConditionsOperation in experiment
With triethyl orthoformate; sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 24h;
Reference： [1]Location in patent: scheme or table Winters, Michael P.; Robinson, Darius J.; Khine, Hnin Hnin; Pullen, Steven S.; Woska Jr., Joseph R.; Raymond, Ernest L.; Sellati, Rosemarie; Cywin, Charles L.; Snow, Roger J.; Kashem, Mohammed A.; Wolak, John P.; King, Josephine; Kaplita, Paul V.; Liu, Lisa H.; Farrell, Thomas M.; DesJarlais, Renee; Roth, Gregory P.; Takahashi, Hidenori; Moriarty, Kevin J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5541 - 5544]
  • 64
  • [ 919346-88-6 ]
  • [ 6053-81-2 ]
  • 5-(5-[(cyclopentylmethyl)amino]methyl}-3-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With sodium tris(acetoxy)borohydride; acetic acid In dimethyl sulfoxide 112 5-(5-[(cyclopentylmethyl)amino]methyl}-3-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide trifluoroacetate Example 112 5-(5-[(cyclopentylmethyl)amino]methyl}-3-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide trifluoroacetate To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (50 mg, 0.112 mmol) in DMSO (2.0 mL), acetic acid (3 drops), (cyclopentylmethyl)amine (112 mg, 1.123 mmol), and was reacted for 4 h. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was then added and the reaction was stirred overnight. The reaction mixture was purified by reverse phase Gilson Preparatory HPLC to give 8.0 mg of the title compound (14%). LCMS: 529.4 (M+H), Rt 1.61 min and 1.64 min
Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2009/143372, 2009, A1
  • 65
  • [ 318-54-7 ]
  • [ 6053-81-2 ]
  • [ 1188310-03-3 ]
YieldReaction ConditionsOperation in experiment
With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20℃;Reflux; General Procedure for Preparation of AFT20 XYZ; To a mixture of XY (1 eq) and a cyclic derivative Z (1.5 eq) like cyclopentylmethyl amine, cyclopentylethyl amine, cyclohexylmethyl amine, clyclohexylethyl amine, cycloheptylmethyl amine, cycloheptylethyl amine, bicyclo[2.2.2]octan-1-ylmethyl amine, or bicyclo[2.2.2]octan-1-ylethyl amine, in dry THF at -78 C. was added lithium hexamethyldisilazide (3.5 eq). Bicyclo[2.2.2]octan-1-ylmethyl amine was prepared according to the procedures disclosed in Unig and Kahanek (1957) Chem Ber 90:236, Delany and Berchtold (1988) J Org Chem 53:3262-3265, Grob et al. (1958) Helv Chim Acta 41:1191-1197, Whitney et al. (1970) J Med Chem 13:254-260. The resulting solution was warmed to room temperature and subsequently heated to reflux for 16 h. After completion of the reaction (TLC), the mixture was concentrated in vacuo. In case of the non-silyloxyethyl derivatives, the residue was purified either by trituration, column chromatography or preparative HPLC to afford compound XYZ (40-66% yield). In case of the silyloxyethyl compounds, the residue was used in the deprotection step without further purification.; Example 6; N-(cyclopentylmethyl)-1-methyl-1H-indole-3-carboxamide; Synthesised according to the procedure disclosed in Example 1 where X is indole, Y is methyl iodide and Z is cyclopentylmethyl amine. Formula: C16H20N2O; Molecular Weight: 256.3; Mass/charge ratio: 256.2 (100.0%), 257.2 (18.3%), 258.2 (1.8%); Elemental analysis: C, 74.97; H, 7.86; N, 10.93; O, 6.24.
Reference： [1]Patent: US2009/312366,2009,A1 .Location in patent: Page/Page column 11; 13
  • 66
  • [ 32315-10-9 ]
  • [ 1072906-05-8 ]
  • [ 6053-81-2 ]
  • [ 1219729-39-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: bis(trichloromethyl) carbonate; 4-bromo-2-(2-(dimethylamino)ethoxy)aniline With sodium hydrogencarbonate In dichloromethane at 0℃; for 0.5h; Stage #2: cyclopentylmethylamine In dichloromethane at 20℃; 9; 292 To prepare compound 9-5, triphosgen (0.33 equiv) was added to the mixture of 3-2 (1 equiv) and saturated NaHCO3 in DCM at 0 0C. After stirring at 0 0C for 0.5 h, compound 9-2 (1 equiv) was added and the mixture was stirred at room temperature until 3-2 disappeared (detection by analytic HPLC). The mixture was extracted with DCM. The extracts were dried over NaHCO3, concentrated in vacuo to give crude 9-4. Crude 9-4 was purified using flash chromatography. Then, the Suzuki procedure as described above to prepare 9-3 was applied to give crude 9-5. This crude product was then subjected to preparative HPLC to give the final product as a solid.; Example 292. 1 -(Cvclopentylmethyl>3-(2-(2-(dimethylaminokthoxy)-4-( 1 H- pyrazol-4-vPphenvPurea; Procedures in Scheme 9 were utilized to synthesize this compound. LC/MS: C20H29N5O2 (M+ 1) 378. Single peak at both 215 nm and 254 nm in analytical HPLC traces.
Reference： [1]Current Patent Assignee: FENG, Yangbo; LOGRASSO, Philip; SCHROETER, Thomas; YIN, Yan - WO2010/36316, 2010, A1 Location in patent: Page/Page column 113-114
  • 67
  • [ 919346-88-6 ]
  • [ 6053-81-2 ]
  • [ 76-05-1 ]
  • 5-(5-[(cyclopentylmethyl)amino]methyl}-3-thienyl)-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% Stage #1: 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide; cyclopentylmethylamine With acetic acid In dimethyl sulfoxide for 4h; Stage #2: With sodium tris(acetoxy)borohydride In dimethyl sulfoxide Stage #3: trifluoroacetic acid In water; acetonitrile 112 Example 112: 5-(5-{r(cvclopentylmethyl)amino1methyl}-34hienvO-3-ri- (ethylsulfonylM-piperidinvϖ-ifrHndole-7-carboxamide trifluoroacetate; To a solution of 3-[1 -(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1 H-indole-7- carboxamide (50 mg, 0.112 mmol) in DMSO (2.0 mL), acetic acid (3 drops), (cyclopentylmethyl)amine (112 mg, 1.123 mmol), and was reacted for 4h. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was then added and the reaction was stirred overnight. The reaction mixture was purified by reverse phase Gilson Preparatory HPLC to give 8.0 mg of the title compound (14%). LCMS: 529.4 (M+H), Rt 1.61 min and 1.64 min
Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2007/5534, 2007, A2 Location in patent: Page/Page column 150
  • 68
  • [ 6053-81-2 ]
  • [ 1313412-68-8 ]
  • [ 1313414-32-2 ]
YieldReaction ConditionsOperation in experiment
42% In acetonitrile at 75℃; Sealed tube; 6b EXAMPLES 6b4-((Cyclopentylmethylamino)methyl)-6-(3-(methylamino)azetidin-1-yt)pyrimidiA mixture of the compoLind obtained in reference exampfe 9 (100 mg, 0.30 mmoi) cyciopentyimethylamine (303 mg, 3 mmoi) in acetonitrile (2 rnL) was heated at 75°C in a pressure tube overnight. The reaction mixture was evaporated to dryness and diluted with chloroform and water. The phases were separated and the aqueous phase was extracted twice again with chloroform. The combined organic phases were dried over MgS04, concentrated to dryness, and the residue was purified by chromatography over silica gel using mixtures of chloroform/SvleOH of increasing polarity as eluent, providing 50 mg of Boc-protected precursor (yield: 42%). HCI (4 M solution in 1 ,4-dioxane, 5 mL) and MeOH (4 mL) were added to this intermediate and the mixture was stirred at room temperature for 1 hour and then it was evaporated to dryness. The residue was dissolved in MeOH {2 mL) and loaded on a sulfonic resin cartridge (Bond elut SCX-Varian, previously washed with MeOH). The cartridge was eluted with MeOH, that was discarded. It was then eluted with 2 N NH3 solution in MeOH, that was collected and evaporated to dryness providing 34 mg of the title compound (yield: 83%).LC-MS ( Method 2): ¾ = 1.32min; m/z 291 (MH+).
Reference： [1]Current Patent Assignee: PALAU PHARMA SA - WO2011/76878, 2011, A1 Location in patent: Page/Page column 64
  • 69
  • [ 70341-45-6 ]
  • [ 6053-81-2 ]
YieldReaction ConditionsOperation in experiment
With palladium dichloride In ethanol 16.2 Step 2 -Preparation of 1-cyclopentylmethanamine A solution of step-1 intermediate (0.180 g) in ethanol (6 mL) and PdCl2 (0.075 g) was stirred in Parr apparatus under pressure 60 psi for 4-5 h. The reaction mixture was filtered through celite and concentrated the filtrate to get 0.100 g of the desired product. 1HNMR (DMSO-d6): δ 1.20 (m, 4H), 1.72 (m, 4H), 2.09 (s, 1H), 4.19 (s, 2H), 8.19 (s, 2H); MS [M+H]+:100.08.
Reference： [1]Current Patent Assignee: GLENMARK PHARMACEUTICALS LTD - US2012/108583, 2012, A1 Location in patent: Page/Page column 27
  • 70
  • [ 6053-81-2 ]
  • C14H11ClF3NO3 [ No CAS ]
  • [ 1415459-58-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C14H11ClF3NO3 With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: cyclopentylmethylamine In tetrahydrofuran at -78 - 75℃; for 16h; Reflux; 3 General Procedure for the preparation ofXYZ:To a solution of XYInt04 in tetrahydrofuran (THF) at -78°C lithium bis(trimethylsilyl)amide (LiHMDS) was added slowly and the solution was allowed to stir for 20 minutes, followed by the addition of a mono- or bicycloalkylalkyl amine derivative Z at -78°C. The reaction mixture was warmed to room temperature and then refluxed for 16 hours at 75°C. The reaction was quenched with ice water and extracted with ethyl acetate. The combined organic layer was washed with water, brine solution and dried over anhydrous sodium sulfate. The solvent was removed and the residue was purified by flash column chromatography on silica gel with 2% methanol/chloroform to yield XYZ.
Reference： [1]Current Patent Assignee: AFFECTIS PHARMACEUTICALS - WO2012/163792, 2012, A1 Location in patent: Page/Page column 26-29
  • 71
  • 6-chloro-3-isopropylpyrimidine-2,4(1H,3H)-dione [ No CAS ]
  • [ 6053-81-2 ]
  • 6-((cyclopentylmethyl)amino)-3-isopropylpyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In 1-methyl-pyrrolidin-2-one at 130℃; for 5h; 2 Example 2. Preparation of 6-((Cyclopentylmethyl)amino)-3-isopropylpyrimidine- 2,4(1 H,3HVdione. Compound 2. 6-((Cyclopentylmethyl)amino)-3-isopropylpyrimidine- 2,4(lH,3H)-dione. A solution of 1.3, (50 mg, 0.27 mmol), cyclopentylmethylamine (78 mg, 0.79 mmol) and proton sponge (80 mg, 0.37 mmol) in NMP (0.5 mL) was stirred at 130 °C for 5 h. After cooling to room temperature, the mixture was purified by RP-HPLC: reversed phase high pressure liquid chromatography(Shimadzu, Prominence LC-20AP system equipped with a Phenomenex Gemini-NX CI 8 column), eluting with 20-90% CH3CN in H20 (both containing O.P/oTFA) to give crude sample (31 mg), which was further purified by flash column chromatography (silica gel, eluted with 0-5%> CH3OH in CH2C12) to give 5 mg of the title compound (7%). LC/MS: m/z (ES+) 252 (M+H)+. 1H-NMR (400 MHz, CDC13) δ ppm 10.58 (br s, 1H), 5.18 - 5.11 (m, 1H), 4.93 (app t, J = 4.0 Hz, 1H), 4.83 (s, 1H), 3.00 (m, 2H), 2.17 - 2.10 (m, 1H), 1.84 - 1.76 (m, 2H), 1.68 - 1.53 (m, 4H), 1.43 (d, J = 4.0 Hz, 6H), 1.28 - 1.18 (m, 2H)
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2014/205234, 2014, A1 Location in patent: Paragraph 0075
  • 72
  • [ 10009-70-8 ]
  • [ 6053-81-2 ]
  • [ 775-00-8 ]
  • C20H34N5O7Pol [ No CAS ]
  • [ 79-08-3 ]
  • [ 5763-61-1 ]
  • [ 5332-73-0 ]
  • C57H83F3N9O14Pol [ No CAS ]
Reference： [1]ACS Combinatorial Science,2015,vol. 17,p. 49 - 59
  • 73
  • [ 87411-40-3 ]
  • [ 6053-81-2 ]
  • C19H29NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 5-(3,5-dimethylphenoxy)pentanoic acid With oxalyl dichloride In dichloromethane at 0℃; for 90h; Stage #2: cyclopentylmethylamine With triethylamine In tetrahydrofuran for 1h;
Reference： [1]Nishiyama, Junya; Makita, Yoshimasa; Kihara, Nobuhiro [Organic Letters, 2015, vol. 17, # 1, p. 138 - 141]
  • 74
  • [ 6053-81-2 ]
  • C19H29NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: methanol / 15 h 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux 2.2: 1 h 3.1: dichloromethane / 40 h
Reference： [1]Nishiyama, Junya; Makita, Yoshimasa; Kihara, Nobuhiro [Organic Letters, 2015, vol. 17, # 1, p. 138 - 141]
  • 75
  • [ 6053-81-2 ]
  • C15H21NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol / 15 h 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux 2.2: 1 h
Reference： [1]Nishiyama, Junya; Makita, Yoshimasa; Kihara, Nobuhiro [Organic Letters, 2015, vol. 17, # 1, p. 138 - 141]
  • 76
  • [ 6053-81-2 ]
  • 2-fluoro-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)benzonitrile [ No CAS ]
  • 2-[(cyclopentylmethyl)amino]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% Stage #1: cyclopentylmethylamine; 2-fluoro-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)benzonitrile With pyridine at 140℃; for 2h; Microwave irradiation; Stage #2: With dihydrogen peroxide; potassium carbonate In water; dimethyl sulfoxide at 50℃; for 5h; 5.1.3.2. 2-[(Cyclopentylmethyl)amino]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)benzamide (19). A mixture of 2-fluoro-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)benzonitrile (18) (100 mg, 0.39 mmol), 1-cyclopentylmethanamine(117 mg, 1.18 mmol), and pyridine (4 mL) was heated at 140° C for 2 h under microwave irradiation. The mixture was then concentrated in vacuo. To the residue was added DMSO (4 mL), K2CO3 (109 mg, 0.79 mmol), and 35% aqueous H2O2 solution (191 mg,1.97 mmol). The mixture was stirred at 50° C for 5 h, then quenched with a saturated aqueous Na2S2O3 solution and extracted with EtOAc and 2-propanol. The organic layer was separated,washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silicagel, eluted with MeOH in EtOAc) to give 2-[(cyclopentylmethyl)amino]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)benzamide(61 mg, 44%) as a white solid. 1H NMR (DMSO-d6) d: 1.20-1.32 (2H, m), 1.43-1.68 (4H, m), 1.70-1.84 (2H, m), 2.07-2.23 (1H,m), 3.00-3.05 (2H, m), 6.66 (1H, dd, J = 8.5, 2.1 Hz), 6.79 (1H, d,J = 1.9 Hz), 7.03 (1H, dd, J = 7.7, 5.1 Hz), 7.23 (1H, br s), 7.38 (1H,dd, J = 7.9, 1.1 Hz), 7.76 (1H, d, J = 8.3 Hz), 7.91 (1H, br s), 7.98(1H, dd, J = 5.3, 1.1 Hz), 8.46 (1H, t, J = 5.1 Hz), 11.84 (1H, br s). LC-MS (ESI) m/z = 352.3 [M+H]+.
Reference： [1]Katoh, Taisuke; Takai, Takafumi; Yukawa, Takafumi; Tsukamoto, Tetsuya; Watanabe, Etsurou; Mototani, Hideyuki; Arita, Takeo; Hayashi, Hiroki; Nakagawa, Hideyuki; Klein, Michael G.; Zou, Hua; Sang, Bi-Ching; Snell, Gyorgy; Nakada, Yoshihisa [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 11, p. 2466 - 2475]
  • 77
  • [ 6053-81-2 ]
  • [ 20419-68-5 ]
  • C16H22ClN5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 - 50℃; for 12h;Reflux; 1) DIPEA (900mg, 6.95 mmol) is added in tetrahydroffiran (30 ml), compound SM-i 0(375mg, 2.78 mmol) and compound 2 (600 mg, 2.32 mmol) at room temperature, and stirred for 12 hours at temperature of 500 C., extracted with ethyl acetate, washed with water and brine, dried with sodium sulfate, filtrated and concentrated to obtain yellow solid compound INTI3-16 (700 mg, yield 90%).
Reference： [1]Patent: US2016/207924,2016,A1 .Location in patent: Paragraph 0465; 0467
  • 78
  • [ 120-57-0 ]
  • [ 6053-81-2 ]
  • [ 495-76-1 ]
  • 1-(1,3-benzodioxol-5-yl)-N-(cyclopentylmethyl)methanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% Stage #1: piperonal; cyclopentylmethylamine In dichloromethane at 25℃; Molecular sieve; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 25℃;
Reference： [1]Kuhn, Bernd; Tichý, Michal; Wang, Lingle; Robinson, Shaughnessy; Martin, Rainer E.; Kuglstatter, Andreas; Benz, Jörg; Giroud, Maude; Schirmeister, Tanja; Abel, Robert; Diederich, François; Hert, Jérôme [Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2485 - 2497]
  • 79
  • [ 6053-81-2 ]
  • [ 161957-56-8 ]
  • 3-bromo-N-cyclopentylmethyl-2-fluoro-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; for 4h; 12a) 3-Bromo-N-cyclopentylmethyl-2-fluoro-benzamide A solution of 3-bromo-2-fluoro-benzoic acid (1 .00 g, 4.57 mmol), HATU (1 .74 g, 4.57 mmol), cyclopentylmethylamine (0.712 g, 5.25 mmol) and DIPEA (1 .77 g, 13.7 mmol) in DCM (15 ml_) was stirred for 4 h. The mixture was washed with aqueous NaHC03 and dried by passage through a phase separation cartridge. Concentration to dryness gave the crude product (1 .40g, quantative), used without further purification. LC-MS m/z 300 (M + H) +, 1 .41 (ret. time).
Reference： [1]Patent: WO2017/60854,2017,A1 .Location in patent: Page/Page column 177; 178
  • 80
  • [ 6053-81-2 ]
  • [ 1374298-23-3 ]
  • [ 1374296-39-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-((2,6-dichlorophenyl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro-[4,5-d]imidazole-5-carboxylic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate Stage #2: cyclopentylmethylamine at 20℃; Example-8d {N-(Cyclopropylmethyl)-2-((2,6-dichlorophenyl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide} General procedure: To a solution of compound 22 (0.1 g, 0.26 mmol) in a mixture of DMF (1.0 mL) and THF (5 mL) were added TBTU (0.16 g, 0.51 mmol), Et3N (51.5 g, 0.51 mmol) and stirred at room temperature for 30 mins. Then, cyclopropylmethanamine hydrochloride (0.054 g, 0.51 mmol) was added to the reaction mixture and stirred further at room temperature for 10-14 h. After the reaction completion, the reaction mixture was diluted with water and extracted with ethyl acetate (2 x 50 mL). The organic portion was washed with 10% sodium bisulfite, water, then dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography on neutral alumina using 1-2% of methanol in DCM to afford compound 8d (0.068 g) in 65% yield as off-white solid.
Reference： [1]Muthukaman, Nagarajan; Tambe, Macchindra; Deshmukh, Sanjay; Pisal, Dnyandeo; Tondlekar, Shital; Shaikh, Mahamadhanif; Sarode, Neelam; Kattige, Vidya G.; Pisat, Monali; Sawant, Pooja; Honnegowda, Srinivasa; Karande, Vikas; Kulkarni, Abhay; Behera, Dayanidhi; Jadhav, Satyawan B.; Sangana, Ramchandra R.; Gudi, Girish S.; Khairatkar-Joshi, Neelima; Gharat, Laxmikant A. [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 23, p. 5131 - 5138]
  • 81
  • [ 6053-81-2 ]
  • 3-amino-4-ethynylisothiazole-5-carboxylic acid [ No CAS ]
  • 3-amino-N-(cyclopentylmethyl)-4-ethynyl-isothiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In tetrahydrofuran at 55℃; for 2h; 1.3.iii Step (iii) = Synthesis of 3-amino-N-(cyclopentylmethyl)-4-ethynyl-isothiazole-5-carboxamide: To a stirred solution of 2.2 g of 3-amino-4-ethynyl-isothiazole-5-carboxylic acid (13 mmol) in THF (59mL) was added successively 15 mL of T3P (26 mmol, 50% in THF), 5.4 mL of triethylamine NEt3 (39mmol) and 1.4 g of cyclopentylmethanamine (14 mmol). The reaction mixture was then stirred at 55 °Cfor 2 h. The mixture was concentrated and the residue partitioned between a 2 M aqueous solution ofHC1 and EtOAc. The aqueous phase was extracted twice with EtOAc and the combined organic extracts were dried over sodium sulphate, filtered, concentrated and purified by column chromatography. Yield:1.6 g (49% of theory).‘H-NMR (400 MHz, DM50 6, ppm) 8.09 (t, 1H), 6.40 (br. s, 2H), 4.83 (s, 1H), 3.20 (t, 2H), 2.13-2.06(m, 1H), 1.74-1.47 (m, 6H), 1.27-1.19 (m, 2H).
49% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In tetrahydrofuran at 55℃; for 2h; A1.1.3.iii 1.3 Step (iii) = Synthesis of 3 -amino-N-(cyclopentylmethyl)-4-ethynyl-isothiazole-5-carboxamide: To a stirred solution of 2.2 g of 3-amino-4-ethynyl-isothiazole-5-carboxylic acid (13 mmol) in THF(59 mL) was added successively 15 mL of T3P (26 mmol, 50% in THF), 5.4 mL of triethylamine NEt3(39 mmol) and 1.4 g of cyclopentylmethanamine (14 mmol). The reaction mixture was then stirred at55 °C for 2 h. The mixture was concentrated and the residue partitioned between a 2 M aqueoussolution of HC1 and EtOAc. The aqueous phase was extracted twice with EtOAc and the combinedorganic extracts were dried over sodium sulphate, filtered, concentrated and purified by columnchromatography. Yield: 1.6 g (49% of theory).‘H-NMR (400 MHz, DMSO , ppm) 8.09 (t, 1H), 6.40 (br. s, 2H), 4.83 (s, 1H), 3.20 (t, 2H), 2.13-2.06 (m, 1H), 1.74-1.47 (m, 6H), 1.27-1.19 (m, 2H).
Reference： [1]Current Patent Assignee: BAYER AG - WO2017/207462, 2017, A1 Location in patent: Page/Page column 68; 69
[2]Current Patent Assignee: BAYER AG - WO2017/207395, 2017, A1 Location in patent: Page/Page column 81; 82; 83
  • 82
  • [ 6053-81-2 ]
  • [ 635-93-8 ]
  • C13H16ClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With magnesium sulfate In dichloromethane at 20℃; for 13h; 1 Example 1: Synthesis of Compound 14 SM2 (106 mg, 1.07 mmol, 1.0 eq) was dissolved in dichloromethane (20 mL), SM1 (168 mg, 1.07 mmol, 1.0 eq) and magnesium sulfate (1.00 g) were added and the resulting mixture reacted at ambient temperature 13 Hours. After filtration, the obtained filtrate was spin-dried to obtain a crude product 14-1, which was directly subjected to the next reaction without further purification.Crude product 14-1 was dissolved in ethanol (15 mL) and potassium carbonate (296 mg, 2.14 mmol, 2.0 eq) and methylbenzenesulfonate were added.The acylmethyl isonitrile (250 mg, 1.28 mmol, 1.2 eq) was added and the resulting mixture was heated at reflux for 1 hour. The reaction was also cooled to ambient temperature, water (30 mL) was added, extracted with ethyl acetate (30 mL), dried over anhydrous magnesium sulfate, and the crude product obtained was evaporated to dryness under reduced pressure and washed with PE/EA=5/1 (20 mL). Compound 14, 250 mg, yield 84%.
Reference： [1]Current Patent Assignee: NANJING YAOJIE ANKANG BIOTECHNOLOGY - CN107793360, 2018, A Location in patent: Paragraph 0125; 0126; 0127; 0128
  • 83
  • [ 6053-81-2 ]
  • [ 87-42-3 ]
  • N-(cyclopentylmethyl)-9H-purin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With triethylamine In propan-1-ol for 5h; Reflux; 2.6 4.2.6 6-Cyclopentylmethylaminopurine (4) 6-Chloropurine (0.325g; 2.1mmol),cyclopentanemethylamine (403μl; 2.5mmol) and Et3N (1.5mL; 10.5mmol) were dissolved in propanol (20mL). The reaction mixture was refluxed for 5h and concentrated in vacuo. White solid was precipitated from water and filtrated off. 1H NMR (500MHz) δ 12.85 (s, 1H), 8.13 (s, 1H), 8.05 (s, 1H), 7.61 (s, 1H), 3.66 (partial overlap, 2H), 2.28-2.15 (m, 1H), 1.69-1.58 (m, 2H), 1.58-1.48 (m, 2H), 1.48-1.37 (m, 2H), 1.30-1.16 (m, 2H). 13C NMR (126MHz, DMSO) δ 154.56, 152.83, 150.66, 139.43, 118.24, 45.12, 30.32, 25.30
Reference： [1]Hönig, Martin; Plíhalová, Lucie; Spíchal, Lukáš; Grúz, Jiří; Kadlecová, Alena; Voller, Jiří; Svobodová, Alena Rajnochová; Vostálová, Jitka; Ulrichová, Jitka; Doležal, Karel; Strnad, Miroslav [European Journal of Medicinal Chemistry, 2018, vol. 150, p. 946 - 957]
  • 84
  • [ 6053-81-2 ]
  • methyl 2-{1-[(4-methyl-1,3-thiazol-2-yl)methyl]-5-oxopyrrolidin-2-yl}-2-oxoacetate [ No CAS ]
  • C17H23N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
91 mg In methanol at 20℃; for 2h; 2-[1-(Cyclopentylmethyl)-5-oxopyrrolidin-2-yl]-/v'-cyclopropyl-2-oxoacetamide (FP 310) To a stirring solution of methyl 2-{1-[(4-methyl-1 ,3-thiazol-2-yl)methyl]-5- oxopyrrolidin-2-yl}-2-oxoacetate (I-456, 50% purity, 1.01 g, 1.79 mmol) in MeOH (25 ml_) was added cyclopentylmethanamine (610 μΙ_, 5.38 mmol) and the mixture was stirred at RT under nitrogen for 2 h. The reaction mixture was concentrated in vacuo and purified by flash column chromatography on normal phase silica (50 g SNAP Ultra column, 0-100% EtOAc in heptane gradient) followed by preparative LC (acidic pH, standard elution method) to afford 91 mg of 2-[1-(cyclopentylmethyl)-5-oxopyrrolidin-2- yl]-N-cyclopropyl-2-oxoacetamide as a viscous yellow oil (98% purity, 7%). H NMR (500 MHz, Chloroform-d) δ 1.16-1.26 (m, 2H), 1.52-1.70 (m, 4H), 1.74-1.83 (m, 2H), 1.96-2.05 (m, 1 H), 2.05-2.12 (m, 1 H), 2.36-2.38 (m, 3H), 2.38-2.58 (m, 3H), 3.22-3.28 (m, 2H), 4.29 (d, J= 15.7 Hz, 1 H), 5.17-5.25 (m, 2H), 6.81-6.84 (m, 1 H), 6.92-6.99 (m, 1 H). LC-MS (METCR1603): 98% (UV), Rt= 3.79 min, m/z (ESI+)= 350.2 [M+H]+
Reference： [1]Current Patent Assignee: HAPLOGEN - WO2018/50631, 2018, A1 Location in patent: Paragraph 0893
  • 85
  • [ 6053-81-2 ]
  • 1-(1-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-α]pyridin-7-yl)piperidin-4-yl)ethan-1-one [ No CAS ]
  • 1-(1-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-α]pyridin-7-yl)piperidin-4-yl)-N-(cyclopentylmethyl)ethan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% Stage #1: cyclopentylmethylamine; 1-(1-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-α]pyridin-7-yl)piperidin-4-yl)ethan-1-one With acetic acid In methanol at 20℃; for 2h; Stage #2: With methanol; sodium cyanoborohydride at 20℃; for 0.25h; 2-112 Example 2-112 To a suspension of l-(l-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[l,2-a]pyridin- 7-yl)piperidin-4-yI)ethan-l -one 2-4 ( ISOmg, 0.36 mmol), cycopentylmethanamme 2~5a (35 mg, 0.36 mmol) in CH3OH (5 mL) was added acetic acid (0.1 mL) and the resulting mixture was stirred at room temperature for 2 h. Sodium eyanoborohydride (114 mg, 1.81 mmol) wras added in one portion and the reaction mixture was stirred at room temperature for 15 nun. The reaction mixture was diluted with aqueous sodium bicarbonate solution (20 niL) and the aqueous layer was extracted with CH2CI2 (2 χ 20 mL). The combined organic extracts were washed with brine (20 mL), dried over NaaSCfo, filtered and concentrated . The residue was purified by combi-flash chromatography [silica gel; 5% NH4OH in MeOH: CH2CI2. (1 :9)] to give I-(l-(2-(5-chloro-2,4-dimethox pheryI)imidazo[l ,2- ]pyridin-7- yl)piperidin-4-yl)-N-(cyclopentylmethyl)ethan- 1 -amine 2-6a (60 mg, 36%yeild) as an off- white solid. (1289) ]H NMR (400 MHz, CD3OD): δ 8.00 (d, J= 7.2 Hz, IH), 7.97 (s, IH), 7.84 (s, IH), 6.67 (s, IH), 6.64 (dd, J= 2.4, 7.6 Hz, IH), 6.55 (s, IH), 3.91(s, 3.H), 3.84 (s, 3H), 3.77 (d, J ----- 12.4Hz, 2.H), 2.68-2.61 (m, 2H), 2.55-2.38 (m, 3H), 1.98-1.90 (m, IH), 1.72-1.69 (m, 4H), 1.57-1.46 (ra, 5H) 1.39-1.30 (ra, 2.H), 1.14-1.06 (m, 2H), 0.96 (d, J= 6.8 Hz, 3H); HPLC (Method 11) 98.9% (AUG), = 7.35 mm. ; ESI+APCT-MS m/z 497 [M + H]+.
36% Stage #1: cyclopentylmethylamine; 1-(1-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-α]pyridin-7-yl)piperidin-4-yl)ethan-1-one With acetic acid In methanol at 20℃; for 2h; Stage #2: With sodium cyanoborohydride In methanol at 20℃; for 0.25h; 2-112 Preparation of 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( Cyclopentylmethyl) ethyl-1-amine 2-6a (Example 2-112) For CH3OH (5mL)1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl)Piperidin-4-yl) ethan-1-one 2-4 (150 mg, 0.36 mmol)And a suspension of cyclopentylmethanamine 2-5a (35 mg, 0.36 mmol) in acetic acid (0.1 mL),And the resulting mixture was stirred at room temperature for 2 hours. Add sodium cyanoborohydride (114mg, 1.81mmol) in one portion,And the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with aqueous sodium bicarbonate solution (20 mL),And the aqueous layer was extracted with CH2Cl2 (2 x 20 mL). The combined organic extracts were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated.The residue was purified by combinatorial-fast chromatography analysis [silicone; 5% NH4OH in MeOH: CH2Cl2 (1: 9),Gives 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (Cyclopentylmethyl) ethyl-1-amine 2-6a (60 mg, yield 36%) as an off-white solid.
Reference： [1]Current Patent Assignee: ONCOTHERAPY SCIENCE INC - WO2018/165112, 2018, A1 Location in patent: Page/Page column 145; 147
[2]Current Patent Assignee: ONCOTHERAPY SCIENCE INC - TW2019/43715, 2019, A Location in patent: Paragraph 0478; 0486-0488
  • 86
  • [ 6053-81-2 ]
  • benzyl 4-formylpyrimidin-2-ylcarbamate hydrochloride [ No CAS ]
  • benzyl N-(4-((cyclopentylmethylimino)methyl)pyrimidin-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: benzyl 4-formylpyrimidin-2-ylcarbamate hydrochloride With hydrogenchloride; potassium hydroxide In tetrahydrofuran; water at 15℃; Cooling with ice; Stage #2: cyclopentylmethylamine With potassium carbonate In tetrahydrofuran; dichloromethane; water at 20℃; for 18h; Benzyl-(4-((cyclopentylmethylimino)methyl)pyrimidin-2-yl)carbamate (0419) 45% aq. KOH (0.449 g, 8.00 mmol) was added to an ice-cold solution of crude aldehyde 2 (0.147g, 0.571 mmol) in aq. HCI (2 ml, 8.00 mmol), while the temperature was maintained below 15 °C. To the neutralized solution, CH2CI2 (5 ml) and K2CO3 (0.095 g, 0.685 mmol) were added followed by cyclopentylmethylamine (107 μΙ_, 0.1 13 mmol). The reaction mixture was gradually warmed to room temperature and stirring was continued for 18 h. 1H NMR analysis of the reaction mixture showed complete consumption of the aldehyde. The crude material was used in the next step without isolation.
Reference： [1]Current Patent Assignee: UNIVERSITY OF MELBOURNE - WO2018/201192, 2018, A1 Location in patent: Page/Page column 91; 92
  • 87
  • [ 6053-81-2 ]
  • [ 886762-70-5 ]
  • C12H15BrN2O2 [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 234 - 246
  • 88
  • [ 6053-81-2 ]
  • [ 4755-77-5 ]
  • C10H17NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: cyclopentylmethylamine With triethylamine In dichloromethane at 10℃; for 0.5h; Stage #2: Ethyl oxalyl chloride In dichloromethane at 10℃; for 15h; 63.1 Step 1: synthesis of compound 63-b Compound 63-a (200.00 mg, 2.02 mmol, 1.00 eq) and triethylamine (715.41 mg, 7.07 mmol, 980.02 mL, 3.50 eq) were dissolved in dichloromethane (8.00 mL), and stirred 10°C for 0.5 hour. Compound 1-b (330.41 mg, 2.42 mmol, 270.83 mL, 1.20 eq) was added to the above solution, and the reaction solution was maintained at 10°C and stirred for 15 hours. After the reaction was completed, the reaction solution was added with water (80 mL), and extracted with dichloromethane (80 mL 3 3). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was subjected to column chromatography (petroleum ether : ethyl acetate = 1:0∼4:1) to give the product of compound 63-b (270.00 mg, yield: 65%) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ=7.14 (br. s., 1H), 4.35 (q, J=7.03 Hz, 2H), 3.29 (t, J=6.65 Hz, 2H), 2.03-2.15 (m, 1H), 1.72-1.84 (m, 2H), 1.61-1.70 (m, 2H), 1.50-1.59 (m, 2H), 1.39 (t, J=7.15 Hz, 3H), 1.14-1.30 (m, 2H).
Reference： [1]Current Patent Assignee: SINO BIOPHARMACEUTICAL LIMITED - EP3456711, 2019, A1 Location in patent: Paragraph 0443; 0444

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