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[ CAS No. 944238-89-5 ] {[proInfo.proName]}

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Chemical Structure| 944238-89-5
Chemical Structure| 944238-89-5
Structure of 944238-89-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 944238-89-5 ]

CAS No. :944238-89-5 MDL No. :MFCD09997870
Formula : C11H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RBLOMFQUEUBEBG-IUCAKERBSA-N
M.W : 212.29 Pubchem ID :45789463
Synonyms :

Safety of [ 944238-89-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 944238-89-5 ]

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

  • Downstream synthetic route of [ 944238-89-5 ]

[ 944238-89-5 ] Synthesis Path-Downstream   1~17

  • 2
  • [ 944238-89-5 ]
  • [ 1272972-77-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 1 h / 150 °C 2: potassium acetate; palladium diacetate / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere 3: sodium peroxoborate tetrahydrate / tetrahydrofuran; water / 16 h / 25 °C 4: caesium carbonate / N,N-dimethyl-formamide / 2 h / 40 °C
  • 3
  • [ 944238-89-5 ]
  • [ 1272973-66-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 1 h / 150 °C 2: potassium acetate; palladium diacetate / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere 3: sodium peroxoborate tetrahydrate / tetrahydrofuran; water / 16 h / 25 °C
  • 5
  • [ 944238-89-5 ]
  • [ 108-23-6 ]
  • (1S,4S)-2-tert-butyl 5-isopropyl 2,5-diazabicyclo[2,2,1]heptane-2,5-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.3 g With N-ethyl-N,N-diisopropylamine In ethyl acetate; toluene for 0.166667h; 5.6.154.A Part A. (1S.4Sl-2-tert-Butyl 5-isopropyl 2.5-diazabicyclo[2.2.1Jheptane-2.5-dicarboxylate To a stirred, ambient temperature, solution (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate [113451-59-5] (1.0 g, 5.0 mmol) and Hunig's base [7087-68-5] (1.4 ml, 8.0 mmol) inethyl acetate (120 ml) was slowly added a 1.0M solution of isopropyl chloroformate in toluene (5.120 ml) over the course of 10 minutes. The reaction was allowed to stir over night then was washed withbrine, dried (MgS04), and evaporated to obtain 1.3 g of yellow oil. LRMS (ESI) mjz 285.1 [(M+H)]+,calc'd for C14H24N204: 284.35.
  • 6
  • [ 944238-89-5 ]
  • (1S,4S)-isopropyl 2,5-diazabicyclo[2,2,1]heptane-2-carboxylate hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / toluene; ethyl acetate / 0.17 h 2: hydrogenchloride / methanol / 2 h / 50 °C
  • 7
  • 4,11-dihydroxy-3-[(dimethylamino)methyl]-1H-naphtho[2,3-f]indole-5,10-dione iodomethylate [ No CAS ]
  • [ 944238-89-5 ]
  • 3-(((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)methyl)-4,11-dihydroxy-1H-naphtho[2,3-f]indole-5,10-dione dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: chloroform / 1 h / Reflux 2: hydrogenchloride / methanol; chloroform
  • 8
  • 4,11-dihydroxy-3-[(dimethylamino)methyl]-1H-naphtho[2,3-f]indole-5,10-dione iodomethylate [ No CAS ]
  • [ 944238-89-5 ]
  • C28H29N3O6*2ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
In chloroform for 1h; Reflux; 4.1.3. (S)-4,11-Dihydroxy-3-((pyrrolidin-3-ylamino)methyl)-1Hnaphtho[2,3-f]indole-5,10-dione dihydrochloride (6) General procedure: A stirring solution of iodomethylate 5 (100 mg, 0.2 mmol) and(S)-1-Boc-3-aminopyrrolidine (100 mg, 2.5 mmol) in chloroform (10 mL) was refluxed for 1 h. The mixture was diluted with chloroform (25 mL), washed with water and aqueous solution of NaHCO3 (1%), dried, and evaporated. The residue was purified by column chromatography on silica gel in chloroform-methanol(2:0→2:1). The red solid obtained after evaporation was dissolved in hot chloroform (1 mL), and a solution of HCl in methanol (1.25 N,1 mL) was added. The mixture was stirred overnight and evaporated.The residue was dissolved in hot water (0.5 mL), filtered and then product was precipitated with acetone-ether mixture (1:1),collected by filtration and dried. The yield of dihydrochloride 6 was 58 mg (61%) as a red solid, mp 212-213°C (dec.).
  • 9
  • [ 591-50-4 ]
  • [ 944238-89-5 ]
  • tert-butyl (1S,4S)-5-phenyl-2,5-diazabicyclo[2.2.2]octane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.6 g With tris-(dibenzylideneacetone)dipalladium(0); potassium <i>tert</i>-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene 310.A Example 310. Synthesis of (1R,4R)-2-((6-methoxy-2,3-dihydro-1H-inden-1-yl)methyl)-5- phenyl-2,5-diazabicyclo[2.2.2]octane A. To a solution of (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.2]octane-2-carboxylate (500 mg, 2.36 mmol) in PhMe (30 mL) was added iodobenzene (1.44 g, 7.08 mmol),potassium 2- methylpropan-2-olate (0.79 g, 7.08 mmol) and Pd2(dba)3 (0.22 g, 0.24 mmol), BINAP (0.29 g, 0.47 mmol). The reaction were filtered and concentrated in vacuo. The resulting oil was purified by flash column chromatography with EtOAc (30%) and hexanes (70%) to provide (1S,4S)-tert-butyl 5- phenyl-2,5-diazabicyclo[2.2.2]octane-2-carboxylate (0.6 g, 2.08 mmol) as a yellow oil.
  • 10
  • [ 944238-89-5 ]
  • (1R,4R)-2-((6-methoxy-2,3-dihydro-1H-inden-1-yl)methyl)-5-phenyl-2,5-diazabicyclo[2.2.2]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene 2: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C 3: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
  • 11
  • [ 944238-89-5 ]
  • (1S,4S)-2-phenyl-2,5-diazabicyclo[2.2.2]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene 2: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C
  • 12
  • [ 944238-89-5 ]
  • (6-methoxy-2,3-dihydro-1H-inden-1-yl)((1S,4S)-5-phenyl-2,5-diazabicyclo[2.2.2]octan-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene 2: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C 3: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C
  • 15
  • [ 944238-89-5 ]
  • 4-((4-((1S,4S)-5-(cyclopropanecarbonyl)-2,5-diazabicyclo[2.2.2]octan-2-yl)pyrimidin-2-yl)amino)-N-ethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / 1,4-dioxane / 3 h / 50 °C 2.1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 4 h / 100 °C 3.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 3.2: 4 h
  • 16
  • [ 944238-89-5 ]
  • 5-(5-(4-(2-bromoethoxy)-3-ethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-3-(trifluoromethyl)picolinonitrile [ No CAS ]
  • tert-butyl (1S,4S)-5-(2-(4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-ethylphenoxy)ethyl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 18h; 43 tert- Butyl (lS,4S)-5-(2-(4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo- 6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-ethylphenoxy)ethyl)-2,5- diazabicyclo [2.2.2] octane-2-carboxylate. To a solution of ter/-butyl (lS,4S)-2,5- diazabicyclo[2.2.2]octane-2-carboxylate (0.057 g, 0.27 mmol, 1.2 eq) in DMF (2.26 mL, 0.100 M) was added 5-[5-[4-(2-bromoethoxy)-3-ethyl-phenyl]-8-oxo-6-thioxo-5,7- diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile (0.125 g, 0.23 mmol, 1 eq), (prepared as described herein), and DIEA (0.14 mL, 0.79 mmol, 3.5 eq). The mixture was heated to 60 °C, while stirring for 18 h. After concentration under reduced pressure, the reaction mixture was purified by silica gel column chromatography (0-100% hexane/EtOAc) to give tert- butyl (lS,4S)-5-(2-(4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7- diazaspiro[3.4]octan-5-yl)-2-ethylphenoxy)ethyl)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate (0.130 g, 0.19 mmol, 84.0% yield) as a beige solid. MS (ESI) m/z 685.2 [M+l]+.
  • 17
  • [ 944238-89-5 ]
  • 2-[4-(4-chlorophenyl)-5-(pyridin-4-yl)-1H-imidazol-1-yl]acetic acid 2,2,2-trifluoroacetic acid [ No CAS ]
  • tert-butyl (1S,4S)-5-{2-[4-(4-chlorophenyl)-5-(pyridin-4-yl)-1H-imidazol-1-yl]acetyl}-2,5-diazabicyclo[2.2.2]octane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70 mg With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 20℃; for 1h; 1.8 Synthesis of tert-butyl (1S,4S)-5-{2-[4-(4-chlorophenyl)-5-(pyridin-4-yl)-1H-imidazol-1-yl]acetyl}- 2,5-diazabicyclo[2.2.2]octane-2-carboxylate / Intermediate 66 2-[4-(4-Chlorophenyl)-5-(4- pyridyl)imidazol-1-yl]acetic acid;2,2,2-trifluoroacetic acid (Intermediate 2a) (75 mg, 0.137 mmol) and tert-butyl (1S,4S)-2,5-diazabicyclo[2.2.2]octane-2-carboxylate (30 mg, 0.141 mmol) were dissolved in a solution of EtOAc (1.5 mL) and DIPEA (120 uL, 0.687 mmol), then T3P (50%, 165 uL, 0.277 mmol) was added. The reaction was stirred at RT for 1 h. The reaction mixture was diluted with EtOAc and partitioned with water. The organic phase was separated and the aqueous was extracted with DCM/MeOH (9:1). The combined organics were concentrated in vacuo. The crude product was purified via flash chromatography (10 g, silica) eluting with 0-10% 2M ammonia MeOH/DCM to afford the title compound (70 mg, 95% yield) as a yellow solid.1HNMR(400 MHz, DMSO-d6) δ 8.66 - 8.61 (m, 2H), 7.81 - 7.79 (m, 1H), 7.41 - 7.37 (m, 2H), 7.31 - 7.25 (m, 4H), 4.95 - 4.79 (m, 1H), 4.77 - 4.72 (m, 1H), 4.46 - 3.99 (m, 2H), 3.58 - 3.38 (m, 2H), 3.38 - 3.25 (m, 2H), 1.89 - 1.78 (m, 1H), 1.74 - 1.64 (m, 3H), 1.43 (s, 9H). LCMS (Analytical Method H) Rt = 0.55 min, MS (ESIpos): m/z 508.3, 510.3 [M+H]+, Purity = 95%
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