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tert-Butyl N-[6-(methylamino)hexyl]carbamate
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[ CAS No. 1013915-06-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
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Product Details of [ 1013915-06-4 ]

CAS No. :1013915-06-4 MDL No. :MFCD30535604
Formula : C12H26N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZNZSUZGLIJORGM-UHFFFAOYSA-N
M.W : 230.35 Pubchem ID :76179868
Synonyms :

Safety of [ 1013915-06-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 UN#:2735
Hazard Statements:H315-H318-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1013915-06-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1013915-06-4 ]

[ 1013915-06-4 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 1013915-06-4 ]
  • [ 393582-75-7 ]
  • [ 1013915-08-6 ]
YieldReaction ConditionsOperation in experiment
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In tetrahydrofuran 8 Starting from m-chloroaniline, which was diazotised and coupled with ethyl α-methylacetoacetate, the azo-ester was converted into ethyl pyruvate m-chlorophenylhydrazone 1 (the Japp-Klingeman reaction). Polyphosphoric acid facilitated the conversion to molecule 2. Next, N-methylation with dimethylcarbonate in presence K2CO3 yielded the ester 3 and was treated with hydrazine and converted into hydrazide 4. The ring was closed in the presence of POCl3 and compound 5 was obtained. N-phenylation with using PhI and CuI (as catalyst) provide compound 6. Mild hydrolysis with dilute KOH in EtOH yield acid 7. To conjugated mono-N-BOC protected N-methyl-1,6-hexanediamine to 7 used BOP. Removal of protecting group with TFA in CH2Cl2 is yields 8.
Reference： [1]Current Patent Assignee: VANDERBILT UNIVERSITY - US2006/147379, 2006, A1 Location in patent: Page/Page column 16-17
  • 2
  • [ 75950-19-5 ]
  • [ 74-89-5 ]
  • [ 1013915-06-4 ]
YieldReaction ConditionsOperation in experiment
85% In ethanol at 80℃; for 16h; Inert atmosphere; 2 Step 2 -Tert-butyl N-[6-(methylamino)hexyl]carbamate To a solution of 6-(tert-butoxycarbonylamino)hexyl methanesulfonate (1.50 g, 5.08 mmol) in EtOH (15 mL) was added MeNH2 (10.5 g, 101 mmol, 30% solution). The mixture was stirred at 80 °C for 16 hrs. On completion, the mixture was concentrated in vacuo. The residue was purified by silica gel column (EA: MeOH = 5: 1) to give the title compound (1 g, 85% yield) as yellow solid.1H NMR (400MHz, DMSO-d6) d 8.33 (s, 1H), 6.77 (s, 1H), 2.94 - 2.79 (m, 4H), 2.32 (s, 3H), 1.60 - 1.47 (m, 2H), 1.41 - 1.32 (m, 11H), 1.31 - 1.20 (m, 4H).
58% With triethylamine In 1,4-dioxane; water at 60℃; for 1h;
Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2020/113233, 2020, A1 Location in patent: Paragraph 00962; 002888; 002891-002892
[2]Labriere, Christophe; Elumalai, Vijayaragavan; Staffansson, Jannie; Cervin, Gunnar; Le Norcy, Tiffany; Denardou, Hugo; Réhel, Karine; Moodie, Lindon W. K.; Hellio, Claire; Pavia, Henrik; Hansen, Jørn H.; Svenson, Johan [Journal of Natural Products, 2020, vol. 83, # 11, p. 3413 - 3423]
  • 3
  • [ 64-18-6 ]
  • [ 1013915-06-4 ]
  • 4-[4-[[2-[2-[tert-butoxycarbonyl(cyclopropylmethyl)amino]-4-pyridyl]oxazole-4-carbonyl]amino]-3-(difluoromethyl)pyrazol-1-yl]cyclohexanecarboxylic acid hydrochloride [ No CAS ]
  • tert-butyl N-[4-[4-[[1-[4-[(6-(tert-butoxycarbonylamino)hexyl)methylcarbamoyl]cyclohexyl]-3-(difluoromethyl)pyrazol-4-yl]carbamoyl]oxazol-2-yl]-2-pyridyl]-N-(cyclopropylmethyl)carbamate formic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: tert-butyl N-[6-(methylamino)hexyl]carbamate; 4-[4-[[2-[2-[tert-butoxycarbonyl(cyclopropylmethyl)amino]-4-pyridyl]oxazole-4-carbonyl]amino]-3-(difluoromethyl)pyrazol-1-yl]cyclohexanecarboxylic acid hydrochloride With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 2h; Inert atmosphere; Stage #2: formic acid In water; acetonitrile Inert atmosphere; 1 Step 1 -Tert-butyl N-[4-[4-[[1-[4-[6-(tert-butoxycarbonylamino)hexyl-methyl- carbamoyl]cyclohexyl] -3-(difluoromethyl)pyrazol-4-yl]carbamoyl]oxazol-2-yl]-2-pyridyl]-N- (cyclopropylmethyl)carbamate To a solution of tert-butyl N-[6-(methylamino)hexyl]carbamate (70.0 mg, 303 umol, Intermediate ADY) in DMF (6 mL) was added 4-[4-[[2-[2-[tert- butoxycarbonyl(cyclopropylmethyl)amino]-4-pyridyl] oxazole-4-carbonyl]amino]-3- (difluoromethyl)pyrazol-1-yl]cyclohexanecarboxylic acid (140 mg, 233 umol, Intermediate QT), DIPEA (90.6 mg, 701 umol) and HATU (106 mg, 280 umol). The reaction mixture was stirred at 25 °C for 2 hours. On completion, the reaction was quenched with H2O (0.5 mL) and the mixture was concentrated in vacuo. The residue was purified by prep-HPLC (column: Phenomenex Synergi C18150*25*10um; mobile phase: [water(0.225%FA)-ACN]; B%: 70%-100%, 10min) to give the title compound (190 mg, 94% yield, FA salt) as a white solid.1H NMR (400 MHz, DMSO- d6) d 9.76 (s, 1H), 9.00 (s, 1H), 8.59 (d, J = 5.2 Hz, 1H), 8.29 (s, 1H), 8.22 - 8.15 (m, 1H), 7.68 (d, J = 5.2 Hz, 1H), 7.33 - 6.99 (m, 1H), 6.78 - 6.70 (m, 1H), 4.33 - 4.23 (m, 1H), 3.86 (d, J = 6.8 Hz, 2H), 3.36 - 3.31 (m, 3H), 3.25 (t, J = 7.2 Hz, 1H), 3.01 (s, 2H), 2.95 - 2.84 (m, 2H), 2.79 (s, 1H), 2.75 - 2.67 (m, 1H), 2.09 - 2.00 (m, 2H), 1.95 - 1.72 (m, 4H), 1.68 - 1.54 (m, 2H), 1.52 (s, 9H), 1.37 (s, 9H), 1.36 (s, 2H), 1.31 - 1.13 (m, 5H), 0.46 - 0.35 (m, 2H), 0.28 - 0.19 (m, 2H); LC-MS (ESI+) m/z 813.6 (M+H)+.
Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2020/113233, 2020, A1 Location in patent: Paragraph 00962; 003076-003078
  • 4
  • [ 1013915-06-4 ]
  • 4-[4-[[2-[2-[tert-butoxycarbonyl(cyclopropylmethyl)amino]-4-pyridyl]oxazole-4-carbonyl]amino]-3-(difluoromethyl)pyrazol-1-yl]cyclohexanecarboxylic acid hydrochloride [ No CAS ]
  • N-[1-[4-[6-aminohexyl(methyl)carbamoyl]cyclohexyl]-3-(difluoromethyl)pyrazol-4-yl]-2-[2-(cyclopropylmethylamino)-4-pyridyl]oxazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 25 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 15 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2020/113233, 2020, A1
  • 5
  • [ 1013915-06-4 ]
  • tert-butyl N-(cyclopropylmethyl)-N-[4-[4-[[3-(difluoromethyl)-1-(4-formylcyclohexyl)pyrazol-4-yl]carbamoyl]oxazol-2-yl]-2-pyridyl]carbamate [ No CAS ]
  • tert-butyl N-[4-[4-[[1-[4-[[(6-(tert-butoxycarbonylamino)hexyl)methylamino]methyl]cyclohexyl]-3-(difluoromethyl)pyrazol-4-yl]carbamoyl]oxazol-2-yl]-2-pyridyl]-N-(cyclopropylmethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: tert-butyl N-[6-(methylamino)hexyl]carbamate; tert-butyl N-(cyclopropylmethyl)-N-[4-[4-[[3-(difluoromethyl)-1-(4-formylcyclohexyl)pyrazol-4-yl]carbamoyl]oxazol-2-yl]-2-pyridyl]carbamate With acetic acid In tetrahydrofuran; N,N-dimethyl-formamide at -10℃; for 0.5h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran; N,N-dimethyl-formamide at -10℃; for 1h; Inert atmosphere; 1 Step 1 - Tert-butyl N-[4-[4-[[1-[4-[[6-(tert-butoxycarbonylamino) hexyl-methyl- amino] methyl]cyclohexyl]-3-(difluoromethyl)pyrazol-4-yl]carbamoyl]oxazol-2-yl]-2-pyridyl]- N-(cyclopropylmethyl)carbamate To a solution of tert-butyl N-[6-(methylamino)hexyl]carbamate (51.2 mg, 222 umol, Intermediate ADY), tert-butyl N-(cyclopropylmethyl)-N-[4-[4-[[3-(difluoromethyl)-1-(4- formylcyclohexyl)pyrazol-4-yl]carbamoyl]oxazol-2-yl]-2-pyridyl]carbamate (100 mg, 171 umol, Intermediate PW) in a mixed solvent of DMF (1.00 mL) and THF (4.00 mL) was added HOAc (30.8 mg, 513 umol) at -10 °C, the mixture was stirred at -10 °C for 0.5 hr , then NaBH(OAc)3(72.5 mg, 342 umol) was added, the mixture was stirred at -10 °C for 1 hr. On completion, the mixture was quenched with H2O (15 mL) and extracted with EA (2 X 15 mL). The organic layers were washed with brine (2 X 15 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound (130 mg, 95% yield) as yellow solid,1H NMR (400MHz, DMSO- d6) d 9.81 (s, 1H), 9.02 (s, 1H), 8.62 - 8.58 (m, 1H), 8.30 (s, 1H), 8.20 (s, 1H), 7.96 (s, 1H), 7.69 (dd, J = 1.2, 5.2 Hz, 1H), 7.32 - 7.01 (m, 1H), 6.79 (t, J = 5.2 Hz, 1H), 4.32 - 4.16 (m, 1H), 3.87 (d, J = 7.2 Hz, 2H), 2.95 - 2.90 (m, 2H), 2.90 - 2.87 (m, 2H), 2.68 - 2.66 (m, 1H), 2.53 - 2.52 (m, 2H), 2.11 - 2.03 (m, 2H), 1.96 - 1.74 (m, 8H), 1.70 - 1.55 (m, 2H), 1.52 (s, 9H), 1.42 - 1.34 (m, 11H), 1.31 - 1.21 (m, 4H), 1.20 - 1.11 (m, 4H), 0.44 - 0.38 (m, 2H), 0.27 - 0.22 (m, 2H).
Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2020/113233, 2020, A1 Location in patent: Paragraph 00962; 002893-002895
  • 6
  • [ 1013915-06-4 ]
  • tert-butyl N-(cyclopropylmethyl)-N-[4-[4-[[3-(difluoromethyl)-1-(4-formylcyclohexyl)pyrazol-4-yl]carbamoyl]oxazol-2-yl]-2-pyridyl]carbamate [ No CAS ]
  • N-[1-[4-[[6-aminohexyl(methyl)amino]methyl]cyclohexyl]-3-(difluoromethyl)pyrazol-4-yl]-2-[2-(cyclopropylmethylamino)-4-pyridyl]oxazole-4-carboxamide hydrochloride salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetic acid / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h / -10 °C / Inert atmosphere 1.2: 1 h / -10 °C / Inert atmosphere 2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 15 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2020/113233, 2020, A1
  • 7
  • [ 75937-12-1 ]
  • [ 1013915-06-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.5 h / 0 - 15 °C 2: ethanol / 16 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 5 h / 0 - 20 °C 2: triethylamine / 1,4-dioxane; water monomer / 1 h / 60 °C
Multi-step reaction with 3 steps 1: triethylamine; dmap / dichloromethane / 0 - 20 °C 2: potassium carbonate; sodium iodide / acetonitrile / 80 °C / Inert atmosphere 3: palladium on activated charcoal; hydrogen / methanol / 40 °C
Multi-step reaction with 2 steps 1.1: Dess-Martin periodane / dichloromethane / 2 h 2.1: methanol; ethanol / 3 h 2.2: 0.5 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: KYMERA THERAPEUTICS INC - WO2020/113233, 2020, A1
[2]Labriere, Christophe; Elumalai, Vijayaragavan; Staffansson, Jannie; Cervin, Gunnar; Le Norcy, Tiffany; Denardou, Hugo; Réhel, Karine; Moodie, Lindon W. K.; Hellio, Claire; Pavia, Henrik; Hansen, Jørn H.; Svenson, Johan [Journal of Natural Products, 2020, vol. 83, # 11, p. 3413 - 3423]
[3]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
[4]Current Patent Assignee: BACAINN BIOTHERAPEUTICS - WO2022/5881, 2022, A1
  • 8
  • [ 24424-99-5 ]
  • [ 1013915-06-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C 3: triethylamine / 1,4-dioxane; water / 1 h / 60 °C
Multi-step reaction with 4 steps 1: methanol / 2 h / 20 °C 2: triethylamine; dmap / dichloromethane / 0 - 20 °C 3: potassium carbonate; sodium iodide / acetonitrile / 80 °C / Inert atmosphere 4: palladium on activated charcoal; hydrogen / methanol / 40 °C
Reference： [1]Labriere, Christophe; Elumalai, Vijayaragavan; Staffansson, Jannie; Cervin, Gunnar; Le Norcy, Tiffany; Denardou, Hugo; Réhel, Karine; Moodie, Lindon W. K.; Hellio, Claire; Pavia, Henrik; Hansen, Jørn H.; Svenson, Johan [Journal of Natural Products, 2020, vol. 83, # 11, p. 3413 - 3423]
[2]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
  • 9
  • [ 4048-33-3 ]
  • [ 1013915-06-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 20 °C 2: triethylamine / dichloromethane / 5 h / 0 - 20 °C 3: triethylamine / 1,4-dioxane; water / 1 h / 60 °C
Multi-step reaction with 4 steps 1: methanol / 2 h / 20 °C 2: triethylamine; dmap / dichloromethane / 0 - 20 °C 3: potassium carbonate; sodium iodide / acetonitrile / 80 °C / Inert atmosphere 4: palladium on activated charcoal; hydrogen / methanol / 40 °C
Reference： [1]Labriere, Christophe; Elumalai, Vijayaragavan; Staffansson, Jannie; Cervin, Gunnar; Le Norcy, Tiffany; Denardou, Hugo; Réhel, Karine; Moodie, Lindon W. K.; Hellio, Claire; Pavia, Henrik; Hansen, Jørn H.; Svenson, Johan [Journal of Natural Products, 2020, vol. 83, # 11, p. 3413 - 3423]
[2]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
  • 10
  • [ 1013915-06-4 ]
  • C28H42BrN5O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C 1.2: 20 °C 1.3: 3 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3 h / 20 °C
Reference： [1]Labriere, Christophe; Elumalai, Vijayaragavan; Staffansson, Jannie; Cervin, Gunnar; Le Norcy, Tiffany; Denardou, Hugo; Réhel, Karine; Moodie, Lindon W. K.; Hellio, Claire; Pavia, Henrik; Hansen, Jørn H.; Svenson, Johan [Journal of Natural Products, 2020, vol. 83, # 11, p. 3413 - 3423]
  • 11
  • [ 1013915-06-4 ]
  • 2-(6-Bromo-1H-indol-3-yl)-N-(6-guanidinohexyl)-N-methylacetamide Trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C 1.2: 20 °C 1.3: 3 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3 h / 20 °C 3.1: dichloromethane / 2 h / 20 °C
Reference： [1]Labriere, Christophe; Elumalai, Vijayaragavan; Staffansson, Jannie; Cervin, Gunnar; Le Norcy, Tiffany; Denardou, Hugo; Réhel, Karine; Moodie, Lindon W. K.; Hellio, Claire; Pavia, Henrik; Hansen, Jørn H.; Svenson, Johan [Journal of Natural Products, 2020, vol. 83, # 11, p. 3413 - 3423]
  • 12
  • [ 152213-66-6 ]
  • [ 1013915-06-4 ]
  • N-(6-aminohexyl)-2-(6-bromo-1H-indol-3-yl)-N-methylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% Stage #1: 2-(6-bromo-1H-indol-3-yl)acetic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.5h; Stage #2: tert-butyl N-[6-(methylamino)hexyl]carbamate In dichloromethane at 20℃; Stage #3: With trifluoroacetic acid In dichloromethane at 20℃; for 3h;
Reference： [1]Labriere, Christophe; Elumalai, Vijayaragavan; Staffansson, Jannie; Cervin, Gunnar; Le Norcy, Tiffany; Denardou, Hugo; Réhel, Karine; Moodie, Lindon W. K.; Hellio, Claire; Pavia, Henrik; Hansen, Jørn H.; Svenson, Johan [Journal of Natural Products, 2020, vol. 83, # 11, p. 3413 - 3423]
  • 13
  • tert-butyl (6-(benzyl(methyl)amino)hexyl)carbamate [ No CAS ]
  • [ 1013915-06-4 ]
YieldReaction ConditionsOperation in experiment
100% With palladium on activated charcoal; hydrogen In methanol at 40℃;
Reference： [1]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1 Location in patent: Paragraph 0333; 0336; 0354; 0357
  • 14
  • [ 1013915-06-4 ]
  • tert-butyl (6-(methyl(6-((4-methyl-9-oxo-9H-thioxanthen-1-yl)amino)hexyl)amino)hexyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; sodium iodide / acetonitrile / 60 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 30 °C 3: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / N,N-dimethyl-formamide / 100 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
  • 15
  • [ 1013915-06-4 ]
  • 1-((6-((6-aminohexyl)(methyl)amino)hexyl)amino)-4-methyl-9H-thioxanthen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; sodium iodide / acetonitrile / 60 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 30 °C 3: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / N,N-dimethyl-formamide / 100 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
  • 16
  • [ 1013915-06-4 ]
  • 1,1’-(((methylazanediyl)bis(hexane-6,1-diyl))bis(azanediyl))bis(4methyl-9H-thioxanthen-9-one) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate; sodium iodide / acetonitrile / 60 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 30 °C 3: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / N,N-dimethyl-formamide / 100 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 5: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / N,N-dimethyl-formamide / 100 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
  • 17
  • [ 1013915-06-4 ]
  • tert-butyl (6-((6-aminohexyl)(methyl)amino)hexyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sodium iodide / acetonitrile / 60 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 30 °C
Reference： [1]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
  • 18
  • [ 1013915-06-4 ]
  • tert-butyl (6-((6-((6-chloro-2-methoxyacridin-9-yl)amino)hexyl)(methyl)amino)hexyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate; sodium iodide / acetonitrile / 60 °C / Inert atmosphere 2.1: palladium on activated charcoal; hydrogen / methanol / 30 °C 3.1: phenol / 0.5 h / 105 °C 3.2: 105 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
  • 19
  • [ 1013915-06-4 ]
  • N1-(6-aminohexyl)-N6-(6-chloro-2-methoxyacridin-9-yl)-N1-methylhexane-1,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate; sodium iodide / acetonitrile / 60 °C / Inert atmosphere 2.1: palladium on activated charcoal; hydrogen / methanol / 30 °C 3.1: phenol / 0.5 h / 105 °C 3.2: 105 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
  • 20
  • [ 1013915-06-4 ]
  • 1-((6-((6-((6-chloro-2-methoxyacridin-9-yl)amino)hexyl)(methyl)amino)hexyl)amino)-4-methyl-9H-thioxanthen-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate; sodium iodide / acetonitrile / 60 °C / Inert atmosphere 2.1: palladium on activated charcoal; hydrogen / methanol / 30 °C 3.1: phenol / 0.5 h / 105 °C 3.2: 105 °C / Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 5.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / N,N-dimethyl-formamide / 100 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
  • 21
  • [ 1013915-06-4 ]
  • [ 51224-12-5 ]
  • benzyl tert-butyl ((methylazanediyl)bis(hexane-6,1-diyl))dicarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.9% With potassium carbonate; sodium iodide In acetonitrile at 60℃; Inert atmosphere;
Reference： [1]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1 Location in patent: Paragraph 0333; 0339; 0354; 0360
  • 22
  • [ 86536-92-7 ]
  • [ 1013915-06-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; sodium iodide / acetonitrile / 80 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 40 °C
Reference： [1]Current Patent Assignee: REYOUNG DRUG DISCOVERY; REYOUNG - WO2021/142065, 2021, A1
  • 23
  • [ 1013915-06-4 ]
  • [ 57-66-9 ]
  • C25H43N3O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-[(dipropylamino)sulfonyl]benzoic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: tert-butyl (6-(methylamino)hexyl)carbamate In N,N-dimethyl-formamide at 0 - 20℃; for 18h; 1 N-(6-((2-Chloropyrimidin-4-yl)amino)hexyl)-4-(N,N-dipropylsulfamoyl)-N- methylbenzamide (BT053). Triethylamine (10.3 mL, 73.6 mmol) was added to a solution of 4- (N,N-dipropylsulfamoyl)benzoic acid 1.1 (5.25 g, 18.4 mmol) dissolved in DMF (46.0 mL). Then HATU (7.07 g, 18.4 mmol) was added in the mixture at 0 °C and stirred for 5 min. A solution of tert-butyl (6-(methylamino)hexyl)carbamate 4.2 (4.24 g, 18.4 mmol) was added dropwise over 15 min to the mixture at 0 °C and the reaction was allowed to slowly warm up to room temperature and stirred for 18 h. Then EtOAc (50 mL) and water (50 mL) were added, the organic layer was washed with water (2 x 50 mL), washed with a saturated solution of NaHCCh (1 x 50 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure affording crude Boc protected amine (8.0 g, 93%) and was used without purification for the next step. LC-MS: RT = 1.86 min; MS cal.: 497.69; Mass found: [M- Boc+H]: 398.3. Trifluoroacetic acid (11.4 mL, 148 mmol) was added to a solution of crude dissolved in DCM (36.9 mL). The reaction was stirred for 5 h at room temperature. The reaction was followed by LC-MS and starting material was still present. Trifluoroacetic acid (2.0 mL) was added and the reaction stirred for 18 h. The mixture was washed with a saturated solution of NaHCCh (2 x 20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure affording the crude amine (7.65 g) and was used without purification for the next step. LC-MS: RT = 1.34 min; MS cal.: 397.58; Mass found: [M+H]: 398.3. 2,4-Dichloropyrimidine (3.64 g, 23.9 mmol) was added to a solution of crude and triethylamine (20.6 mL, 147 mmol) dissolved in DCM (46.0 mL). The reaction was stirred for 3 h at 0 °C (the reaction was followed by LCMS and wasn't yet completed), Et3N (4.0 mL) was added and the resulting mixture was stirred for 18 h at room temperature. Then water (40 mL) was added and extracted with EtOAc (2 x 40 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude was purified by flash column chromatography (220 g silica, EtOAc in hexanes, 15 to 100%) affording compound BT053 (5.09 g, 54%) as a yellow oil. LC-MS: RT = 1.73 min; Purity: 98.9%; MS cal.: 510.09; Mass found: [M+H]: 510.3. NMR (500 MHz, CDC13) d 7.99 (s, 1H), 7.85 (d, J = 8.1 Hz, 2H), 7.50 (d, J = 7.9 Hz, 2H), 6.26 (d, J = 6.0 Hz, 1H), 5.31 (s, 1H), 3.56 (t, J = 6.9 Hz, 1H), 3.22 - 3.13 (m, 2H), 3.09 (s, 6H), 2.96 (s, 3H), 2.89 (d, J = 11.7 Hz, 2H), 1.84 - 1.46 (m, 12H), 0.88 (t, J = 7.4 Hz, 6H).
Stage #1: 4-[(dipropylamino)sulfonyl]benzoic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: tert-butyl (6-(methylamino)hexyl)carbamate In N,N-dimethyl-formamide at 0 - 20℃; for 18h; 1 N-(6-((2-Chloropyrimidin-4-yl)amino)hexyl)-4-(N,N-dipropylsulfamoyl)-N- methylbenzamide (BT053). Triethylamine (10.3 mL, 73.6 mmol) was added to a solution of 4- (N,N-dipropylsulfamoyl)benzoic acid 1.1 (5.25 g, 18.4 mmol) dissolved in DMF (46.0 mL). Then HATU (7.07 g, 18.4 mmol) was added in the mixture at 0 °C and stirred for 5 min. A solution of tert-butyl (6-(methylamino)hexyl)carbamate 4.2 (4.24 g, 18.4 mmol) was added dropwise over 15 min to the mixture at 0 °C and the reaction was allowed to slowly warm up to room temperature and stirred for 18 h. Then EtOAc (50 mL) and water (50 mL) were added, the organic layer was washed with water (2 x 50 mL), washed with a saturated solution of NaHCCh (1 x 50 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure affording crude Boc protected amine (8.0 g, 93%) and was used without purification for the next step. LC-MS: RT = 1.86 min; MS cal.: 497.69; Mass found: [M- Boc+H]: 398.3. Trifluoroacetic acid (11.4 mL, 148 mmol) was added to a solution of crude dissolved in DCM (36.9 mL). The reaction was stirred for 5 h at room temperature. The reaction was followed by LC-MS and starting material was still present. Trifluoroacetic acid (2.0 mL) was added and the reaction stirred for 18 h. The mixture was washed with a saturated solution of NaHCCh (2 x 20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure affording the crude amine (7.65 g) and was used without purification for the next step. LC-MS: RT = 1.34 min; MS cal.: 397.58; Mass found: [M+H]: 398.3. 2,4-Dichloropyrimidine (3.64 g, 23.9 mmol) was added to a solution of crude and triethylamine (20.6 mL, 147 mmol) dissolved in DCM (46.0 mL). The reaction was stirred for 3 h at 0 °C (the reaction was followed by LCMS and wasn't yet completed), Et3N (4.0 mL) was added and the resulting mixture was stirred for 18 h at room temperature. Then water (40 mL) was added and extracted with EtOAc (2 x 40 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude was purified by flash column chromatography (220 g silica, EtOAc in hexanes, 15 to 100%) affording compound BT053 (5.09 g, 54%) as a yellow oil. LC-MS: RT = 1.73 min; Purity: 98.9%; MS cal.: 510.09; Mass found: [M+H]: 510.3. NMR (500 MHz, CDC13) d 7.99 (s, 1H), 7.85 (d, J = 8.1 Hz, 2H), 7.50 (d, J = 7.9 Hz, 2H), 6.26 (d, J = 6.0 Hz, 1H), 5.31 (s, 1H), 3.56 (t, J = 6.9 Hz, 1H), 3.22 - 3.13 (m, 2H), 3.09 (s, 6H), 2.96 (s, 3H), 2.89 (d, J = 11.7 Hz, 2H), 1.84 - 1.46 (m, 12H), 0.88 (t, J = 7.4 Hz, 6H).
Reference： [1]Current Patent Assignee: BACAINN BIOTHERAPEUTICS - WO2022/5881, 2022, A1 Location in patent: Paragraph 0191; 0206-0207
[2]Current Patent Assignee: BACAINN BIOTHERAPEUTICS - WO2022/5881, 2022, A1 Location in patent: Paragraph 0191; 0206-0207
  • 24
  • [ 1013915-06-4 ]
  • N-(6-((2-chloropyrimidin-4-yl)amino)hexyl)-4-(N,N-dipropylsulfamoyl)-N-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.08 h / 0 °C 1.2: 18 h / 0 - 20 °C 2.1: trifluoroacetic acid / dichloromethane / 5 h / 20 °C 3.1: triethylamine / dichloromethane / 3 h / 0 °C
Reference： [1]Current Patent Assignee: BACAINN BIOTHERAPEUTICS - WO2022/5881, 2022, A1
  • 25
  • [ 1013915-06-4 ]
  • C20H35N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 0.08 h / 0 °C 1.2: 18 h / 0 - 20 °C 2.1: trifluoroacetic acid / dichloromethane / 5 h / 20 °C
Reference： [1]Current Patent Assignee: BACAINN BIOTHERAPEUTICS - WO2022/5881, 2022, A1
  • 26
  • [ 80860-42-0 ]
  • [ 74-89-5 ]
  • [ 1013915-06-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-tert-butoxycarbonylaminohexanal; methylamine In methanol; ethanol for 3h; Stage #2: With methanol; sodium tetrahydridoborate; ethanol at 0 - 20℃; for 0.5h; 1 tert-Butyl (6-(methylamino)hexyl)carbamate (4.2). To a solution of tert-butyl (6- hydroxyhexyl)carbamate 4.1 (4.0 g, 18.4 mmol) in DCM (100 mL) at 0 °C was added the periodinane (9.37 g, 22.0 mmol) and the resulting mixture was stirred for 2 h. The reaction was then quenched with a saturated solution of sodium bisulfite (100 mL) and a saturated solution of NaHCCb (100 mL). The phases were separated, and the aqueous phase was extracted with DCM (100 mL). Organic phases were combined and dried over MgS04, filtered and concentrated under reduced pressure to afford the crude aldehyde. Freshly prepared aldehyde in EtOH (80 mL) was stirred at room temperature. After 2 min, the MeNH22M in MeOH (73 mL) was added, and the mixture vigorously stirred. After stirring for 3 h, the resulting mixture was cooled down to 0 °C and NaBH4 (731 mg, 19.3 mmol) was added. The reaction was stirred for 30 min and the resulting mixture was quenched with a saturated solution of NaHC03 and the organic material was extracted with DCM (3 x 300 mL), dried over sodium sulfate and concentrated under reduced pressure affording crude 4.2 (4.2 g, 99%). LC-MS: RT = 1.09 min; MS cal.: 230.35; Mass found: [M-Boc+H]: 175.0. NMR (500 MHz, CDC13) d 4.51 (s, 1H), 3.10 (d, J = 6.0 Hz, 2H), 2.64 - 2.52 (m, 2H), 2.43 (s, 3H), 1.54 - 1.46 (m, 4H), 1.44 (s, 9H), 1.33 (dd, J = 6.7, 2.9 Hz, 4H).
Stage #1: 6-tert-butoxycarbonylaminohexanal; methylamine In methanol; ethanol for 3h; Stage #2: With methanol; sodium tetrahydridoborate; ethanol at 0 - 20℃; for 0.5h; 1 tert-Butyl (6-(methylamino)hexyl)carbamate (4.2). To a solution of tert-butyl (6- hydroxyhexyl)carbamate 4.1 (4.0 g, 18.4 mmol) in DCM (100 mL) at 0 °C was added the periodinane (9.37 g, 22.0 mmol) and the resulting mixture was stirred for 2 h. The reaction was then quenched with a saturated solution of sodium bisulfite (100 mL) and a saturated solution of NaHCCb (100 mL). The phases were separated, and the aqueous phase was extracted with DCM (100 mL). Organic phases were combined and dried over MgS04, filtered and concentrated under reduced pressure to afford the crude aldehyde. Freshly prepared aldehyde in EtOH (80 mL) was stirred at room temperature. After 2 min, the MeNH22M in MeOH (73 mL) was added, and the mixture vigorously stirred. After stirring for 3 h, the resulting mixture was cooled down to 0 °C and NaBH4 (731 mg, 19.3 mmol) was added. The reaction was stirred for 30 min and the resulting mixture was quenched with a saturated solution of NaHC03 and the organic material was extracted with DCM (3 x 300 mL), dried over sodium sulfate and concentrated under reduced pressure affording crude 4.2 (4.2 g, 99%). LC-MS: RT = 1.09 min; MS cal.: 230.35; Mass found: [M-Boc+H]: 175.0. NMR (500 MHz, CDC13) d 4.51 (s, 1H), 3.10 (d, J = 6.0 Hz, 2H), 2.64 - 2.52 (m, 2H), 2.43 (s, 3H), 1.54 - 1.46 (m, 4H), 1.44 (s, 9H), 1.33 (dd, J = 6.7, 2.9 Hz, 4H).
Reference： [1]Current Patent Assignee: BACAINN BIOTHERAPEUTICS - WO2022/5881, 2022, A1 Location in patent: Paragraph 0191; 0206
[2]Current Patent Assignee: BACAINN BIOTHERAPEUTICS - WO2022/5881, 2022, A1 Location in patent: Paragraph 0191; 0206
  • 27
  • [ 4048-33-3 ]
  • [ 24424-99-5 ]
  • [ 74-89-5 ]
  • [ 1013915-06-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-aminohexan-1-ol; di-<i>tert</i>-butyl dicarbonate With triethylamine for 2h; Stage #2: With methanesulfonyl chloride; triethylamine at 0℃; for 5h; Stage #3: methylamine at 60℃; for 1h;
Reference： [1]Elumalai, Vijayaragavan; Trobec, Tomaž; Grundner, Maja; Labriere, Christophe; Frangež, Robert; Sepčić, Kristina; Hansen, Jørn H.; Svenson, Johan [Organic and Biomolecular Chemistry, 2022]
  • 28
  • [ 152213-66-6 ]
  • [ 1013915-06-4 ]
  • 2-(6-Bromo-1H-indol-3-yl)-N-(6-guanidinohexyl)-N-methylacetamide Trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / 1.5 h 1.2: 4 h 2.1: N-ethyl-N,N-diisopropylamine / 3 h 2.2: 4 h
Reference： [1]Elumalai, Vijayaragavan; Trobec, Tomaž; Grundner, Maja; Labriere, Christophe; Frangež, Robert; Sepčić, Kristina; Hansen, Jørn H.; Svenson, Johan [Organic and Biomolecular Chemistry, 2022]
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