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[ CAS No. 886766-28-5 ]

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Chemical Structure| 886766-28-5
Chemical Structure| 886766-28-5
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Product Details of [ 886766-28-5 ]

CAS No. :886766-28-5 MDL No. :MFCD08685931
Formula : C11H20N2O2 Boiling Point : 301.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :212.29 g/mol Pubchem ID :46942212
Synonyms :

Safety of [ 886766-28-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 886766-28-5 ]

  • Downstream synthetic route of [ 886766-28-5 ]

[ 886766-28-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 591-50-4 ]
  • [ 886766-28-5 ]
  • [ 1254981-66-2 ]
YieldReaction ConditionsOperation in experiment
31% With cesium hydroxide; In dimethyl sulfoxide; at 120℃; for 0.666667h;Sealed tube; A stirred solution of <strong>[886766-28-5]4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester</strong> (0.1 g, 0.471 mmol) [C.A.S. 886766-28-5] , iodobenzene (0.026 ml, 0.236) and CsOH (0.079 g, 0.471 mmol) in DMSO (1 ml) was heated in a sealed tube at 1200C for 20 min. After cooling, additional <strong>[886766-28-5]4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester</strong> (2 eq.) was added, and the mixture was then heated at 1200C for 20 min. The mixture was cooled.The mixture was washed with NH4Cl (aqueous sat. solution) was added and extracted with Et2O. The organic phase was separated, washed with water, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by manifold (Sep-Pak.(R). silica cartridge; DCM as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate D61 (0.021 g, 31percent) as a white solid.
  • 3
  • [ 886766-28-5 ]
  • [ 1200114-08-4 ]
YieldReaction ConditionsOperation in experiment
Step 2:4-(trifluoroacetyl)-4,7-diazaspiro[2.5]octane hydrochloridePyridine (500 mul) and trifluoroacetic anhydride (786 mul, 5.64 mmol) were added to a dichloromethane (10 ml) solution of the compound (1.0 g, 4.70 mmol) obtained in Step 1 above under ice cooling and the resulting mixture was stirred for 15 minutes.After completion of the reaction, trifluoroacetic acid (6 ml) was added and the resulting mixture was stirred at room temperature for 1 hour.The reaction solvent was evaporated under reduced pressure and then the residue was subjected to azeotropic distillation with toluene.The residue was diluted with chloroform and the organic layer was washed with saturated aqueous sodium bicarbonate solution and brine and dried over anhydrous sodium sulfate.The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [chloroform:methanol = 40:1 (v/v)].The residue obtained was subjected to azeotropic distillation with 4 N hydrochloric acid/dioxane and then dried under reduced pressure to give the title compound (751 mg, 65percent) as a colorless solid.1H-NMR (400 MHz, DMSO-d6) delta: 1.15-1.21 (4H, m), 3.14-3.19 (2H, m), 3.24 (2H, t, J=5.4 Hz), 3.84-3.91 (2H, m).MS (ESI) m/z: 209 [(M+H)+].
  • 4
  • [ 886766-28-5 ]
  • [ 1403676-74-3 ]
  • tert-butyl 4-((1s,4s)-4-((2-fluoro-4-(methylsulfonyl)phenoxy)methyl)cyclohexyl)-4,7-diazaspiro[2.5]octane-7-carboxylate [ No CAS ]
  • tert-butyl 4-((1r,4r)-4-((2-fluoro-4-(methylsulfonyl)phenoxy)methyl)cyclohexyl)-4,7-diazaspiro[2.5]octane-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.4%; 2.3% To a solution of tert-b tyl 4,7-diazaspiro[2.5]octane-7-carboxylate (0.16 g, 0.73 mmol) and 4-((2-fluoro-4-(methylsulfonyl)phenoxy)methyl)cyclohexanone (0.20 g, 0.67 mmol) in DCE (5 mL) at room temperature under nitrogen was added acetic acid (76.0 mu, 1.30 mmol) and sodium triacetoxyborohydride (0.35 g, 1.7 mmol). The mixture was heated at 45 °C for 3 days. The reaction formed a major side product (alcohol) from ketone starting material. The mixture was quenched with saturated NaHC03 (aq.). The organic layer was separated and the aqueous layer was extracted once with DCM. The combined organic phases were concentrated under reduced pressure and purified by preparative HPLC. The pure fractions were combined, neutralized with saturated NaHC03 (aq.), and concentrated under reduced pressure. The aqueous residue was extracted twice with DCM and the combined organic layers were dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford the more polar title compound as an off-white gum (7.7 mg, 2.3percent). The less polar cis analog was also obtained as an off-white gum (1.2 mg, 0.4percent). Exact mass calculated for C25H37FN2O5S: 496.2, found: LCMS m/z = 497.4 [M+H]+; lU NMR (400 MHz, CDC13) delta ppm 0.55-0.64 (m, 2H), 0.66-0.72 (m, 2H), 1.08-1.36 (m, 4H), 1.45 (s, 9H), 1.75-1.89 (m, 1H), 1.93-2.02 (m, 2H), 2.09-2.18 (m, 2H), 2.87-2.97 (m, 1H), 3.03 (s, 3H), 3.08-3.13 (m, 2H), 3.17 (s, 2H), 3.40 (bs, 2H), 3.90 (d, J = 6.32 Hz, 2H), 7.06 (t, J = 8.21 Hz, 1H), 7.62-7.66 (m, 1H), 7.66-7.70 (m, 1H).
  • 5
  • [ 886766-28-5 ]
  • 3-methyl-1-(tetrahydropyran-2-yl)-6-[4-(tetrahydropyran-2-yloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid sodium salt [ No CAS ]
  • 4-{3-methyl-1-(tetrahydropyran-2-yl)-6-[4-(tetrahydropyran-2-yloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carbonyl}-4,7-diazaspiro[2.5]octane-7-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; To a suspension of 300 mg of 3-methyl-1 -(tetrahydro-pyran-2-yl)-6-[4-(tetrahydro- pyran-2-yloxy)-phenyl]-1 H-pyrazolo[3,4-b]pyridine-4-carboxylic acid sodium salt in 7.5 ml of DCM were added 0.12 ml of Hunig's base, 376 mg of BEP and 146 mg of<strong>[886766-28-5]4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester</strong>. The reaction was stirred overnight at r.t.. For workup it was diluted with water and DCM and the layers were separated. The organic layer was washed with water twice, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, heptane/EtOAc gradient) to obtain 280 mg (66%) of the title compound. LC/MS (Method LC4): Rt = 1 .24 min; m/z = 632.20 [M+H]+.
  • 6
  • [ 886766-28-5 ]
  • [ 823-62-1 ]
  • tert-butyl 4-(5-amino-6-chloro-1,2,4-triazin-3-yl)-4,7-diazaspiro[2.5]octane-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 155℃; for 9.5h;Microwave irradiation; A vial was charged with 5-amino-3,6-dichloro-l,2,4-triazine (108.5 mg, 0.658 mmol), diisopropylethylamine (0.5 mL, 2.87 mmol), tert-butyl 2-(4,7-diazaspiro[2.5]octan-7- yl)acetate (154.8 mg, 0.650 mmol) in dioxane (2.5 mL). The mixture was heated at 155 C for 9.5 h using microwave. The mixture was concentrated to remove all of solvent. The residue was dissolved in dichloromethane, washed with aqueous sodium bicarbonate solution. The organic solution was separated. The aqueous solution was mixed with brine, extracted with dichloromethane (2 x 35 mL). The combined organic solution was dried over anhydrous sulfate, concentrated to afford a residue. The residue was purified with flash column chromatography on silica using 1-10% methanol in dichloromethane to afford product (118.3 mg) in 53% yield. NMR (500 MHz, Chloroform-d) delta 5.24 (s, 2H), 3.91 (t, J = 4.5 Hz, 2H), 3.42 (m, 2H), 3.33 (s, 2H), 1.43 (s, 9H), 0.96 (m, 4H). MS for C14H21 CIN6O2: 341.2 (MH+).
  • 7
  • [ 886766-28-5 ]
  • [ 98-88-4 ]
  • C18H24N2O3 [ No CAS ]
  • 8
  • [ 886766-28-5 ]
  • [ 98-88-4 ]
  • tert-butyl 4-benzoyl-4,7-diazaspiro[2.5]octane-7-carboxylate [ No CAS ]
  • 9
  • [ 39079-62-4 ]
  • [ 886766-28-5 ]
  • (E)-tert-butyl 4-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)-4,7-diazaspiro[2.5]octane-7-carboxylate [ No CAS ]
  • 10
  • ethyl 2-((1-(((tert-butoxy)carbonyl)amino)cyclopropyl)carbonylamino)acetate [ No CAS ]
  • [ 886766-28-5 ]
  • 11
  • [ 24424-99-5 ]
  • 4,7-diazaspiro[2.5]octane [ No CAS ]
  • [ 886766-28-5 ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydroxide; In ethanol; at 5 - 30℃; for 13h; In the 1L three-mouth reaction bottle,64.9 g of 4,7-diazaspiro[2.5]octane and 650 mL of EtOH were added in sequence.Temperature control below 30 °C,Slowly add 51g NaOH,Temperature control below 5 °C,Add 252.6g (Boc) 2O dropwise,After the addition is completed, slowly rise to room temperature. Stir the reaction at room temperature for 13 h,TLC monitors the reaction completely,filter,Desolvent,Purified by the column49.7-diazaspiro[2.5]octane-7-carboxylic acid tert-butyl ester 89.7 g,The yield was 73percent.
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