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[ CAS No. 1008526-70-2 ] {[proInfo.proName]}

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Chemical Structure| 1008526-70-2
Chemical Structure| 1008526-70-2
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Product Details of [ 1008526-70-2 ]

CAS No. :1008526-70-2 MDL No. :MFCD17015985
Formula : C9H16N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :DUYWGUJDIRKARQ-UHFFFAOYSA-N
M.W : 232.23 Pubchem ID :57415904
Synonyms :

Calculated chemistry of [ 1008526-70-2 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.09
TPSA : 95.59 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 0.44
Log Po/w (WLOGP) : -0.14
Log Po/w (MLOGP) : -0.7
Log Po/w (SILICOS-IT) : -1.69
Consensus Log Po/w : -0.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.23
Solubility : 13.8 mg/ml ; 0.0593 mol/l
Class : Very soluble
Log S (Ali) : -2.02
Solubility : 2.24 mg/ml ; 0.00966 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.15
Solubility : 163.0 mg/ml ; 0.703 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.71

Safety of [ 1008526-70-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1008526-70-2 ]

* 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 [ 1008526-70-2 ]

[ 1008526-70-2 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 398489-26-4 ]
  • [ 75-52-5 ]
  • [ 1008526-70-2 ]
YieldReaction ConditionsOperation in experiment
97% triethylamine; In ethanol; for 18.0h; INTERMEDIATE 333-Hvdroxy-3-(nitromethyl)azetidine-l-carboxylic acid fert-butyl ester; 3-Oxoazetidine-l-carboxylic acid tert-bvAy ester (500 mg, 2.9 mmol) was dissolved in ethanol (1.5 mL) and to this was added nitromethane (0.6 mL) and triethylamine (catalytic). The reaction mixture was stirred for 18 h and the solvent then removed under reduced pressure to yield the title compound as a white solid (650 mg, 97%). deltaH (d6-DMSO) 6.42 (IH, s), 4.86 (2H, s), 4.04 (2H, d, J 9.2 Hz), 3.75 (2H, d, J 9.2 Hz), 1.39 (9H, s). LCMS (ES+) RT (pH 10) 1.73 minutes, 231 (M-H)".
97% With triethylamine; In ethanol; for 8.0h; INTERMEDIATE 103-Hvdroxy-3-(nitromethyl)azetidine-l-carboxylic acid fer/-butyl ester3-Oxoazetidine-l-carboxylic acid tert-butyl ester (500 mg, 2.9 mmol) was dissolved in ethanol (1.5 mL) and to this was added nitromethane (0.6 mL) and triethylamine (cat.). The reaction was stirred for eighteen hours and the solvent was then removed under reduced pressure to yield the title compound as a white solid (650 mg, 97%). ?H (d6-DMSO) 6.42 (IH, s), 4.86 (2H, s), 4.04 (2H, d, J9.2 Hz), 3.75 (2H, d, J9.2 Hz), 1.39 (9H, s). LCMS (ES+) RT (pH 10) 1.73 min (M-H)" 231.
92% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; at 25.0℃; for 19.0h; Compound II-1 (50.0 g, 0.29 mol, 1.0 e.q.), 60 mL of nitromethane, 0.25 mL of DBU, 300 mL of ethanol was placed in a 500 mL four-necked flask.After stirring at 25 C for 15 h, TLC showed that the starting material remained, and added 0.5 mL of DBU, 20 mL of nitromethane, and stirred for 4 h. TLC showed the reaction was complete.The solvent was removed by concentration, and the residue was added with 200 mL of PE and left to stand in the refrigerator overnight.Filter, PE rinse,The compound III-1 after drying was 62.04 g of a pale yellow solid, yield 92%.
With triethylamine; In ethanol; at 20.0℃; for 16.0h; 3-Oxoazetidin -1-carboxylic acid tert-butyl ester (9.00 g, 52.57 mmol) was dissolved in ethanol (30.00 mL) at 20 C, and added with nitromethane (33.90 g, 555.37 mmol) and triethylamine (730.00 mg, 7.21 mmol). The mixture was stirred at 20 C for 16 hours. TLC (PE: EA = 5:1) showed that the reaction was complete. The reaction mixture was concentrated under vacuum to give compound 13A. 1HNMR (400MHz, DMSO-d6) delta = 6.44 (s, 1H), 4.86 (s, 2H), 4.04 (br d, J=8.9 Hz, 2H), 3.74 (br d, J=9.2 Hz, 2H), 1.38 (s, 9H).
With triethylamine; In ethanol; at 20.0℃; for 16.0h; To a solution of tert-butyl 3-oxoazetidine-1-carboxylate (16.0 g, 0.09 mol) in EtOH (150 mL) was added Et 3N (0.95 g, 9.40 mmol) andnitromethane (21.7 g, 0.36 mol) . The mixture was stirred at room temperature for 16 hrs and concentrated to drynessto give desired product (20 g crude) as yellow oil, which was directly used for next step without further purification. MS (ESI) m/z: 233 (M+H) +.

  • 2
  • [ 1008526-70-2 ]
  • [ 1008526-71-3 ]
YieldReaction ConditionsOperation in experiment
68% With hydrogen;palladium 10% on activated carbon; In ethanol; at 50.0℃; under 2585.81 Torr; for 2.0h; INTERMEDIATE 343-(Aminomethyl)-3-hydroxyazetidine-l-carboxylic acid ferf-butyl ester; Intermediate 33 (500 mg, 2.2 mmol) was dissolved in ethanol (40 mL) in a hydrogenation vessel and 10% palladium on charcoal (43 mg) was added. The vessel was charged with hydrogen to 50 psi and heated to 500C. This was then stirred for 2 h and the catalyst was removed by filtering through a plug of celite. The solvent was removed under reduced pressure to yield a pale yellow oil. This was purified by chromatography on an amine column using DCM/MeOH 5% as the eluent to afford the title compound (306 mg, 68%). deltaH (d6-DMSO) 5.50 (IH, s), 3.73 (2H, d, J 8.5 Hz), 3.54 (2H, d, J 8.5 Hz), 2.60 (2H, s), 1.37 (9H, s). Some exchangeable protons were not observed.
68% With hydrogen;palladium 10% on activated carbon; In ethanol; at 50.0℃; under 2585.81 Torr; for 2.0h; INTERMEDIATE 113-(Ammomethyl)-3-hydroxyazetidine trifluoroacetate saltIntermediate 10 (500 mg, 2.2 mmol) was dissolved in ethanol (40 mL) in a hydrogenation vessel and 10% palladium on charcoal (43 mg) was added. The vessel was charged with hydrogen to 50 psi and heated to 5O0C. This was then stirred for 2 h and the catalyst was removed by filtering through a plug of celite. The solvent was removed under reduced pressure to yield a pale yellow oil. The intermediate was purified by chromatography on an amine column using 5% DCM/MeOH as the eluent to afford the BOC-protected amine as an off-white solid (306 mg, 68%). ?H (d6-DMSO) 5.50 (IH, s), 3.73 (2H, d, J8.5 Hz), 3.54 (2H, d, J8.5 Hz), 2.60 (2H, s), 1.37 (9H, s). Some exchangeable protons were not observed. The intermediate BOC-protected amine was dissolved in DCM (10 mL) and trifluoroacetic acid (1 mL) added. The mixture was stirred for 1 hour at room temperature before the volatiles were removed in vacuo to give the title compound, which was used without further purification.
With palladium 10% on activated carbon; hydrogen; In methanol; at 20.0℃; under 775.743 Torr; for 16.0h; 3-Hydroxy-3-(nitromethyl)azetidin-1-carboxylic acid tert-butyl ester (6.00g, 25.84 mmol) was dissolved in methanol (60.00 mL) at 20 C, and added with wet palladium on carbon (10%, 0.6 g) under nitrogen protection. The suspension was degassed, displaced,and purified with hydrogen gas four times, and then stirred under hydrogen atmosphere (15 psi) at 20 C for 16 hours. TLC (petroleum ether: ethyl acetate=): 1) showed that the reaction was complete. The reaction mixture was filtered and concentrated under vacuum to give compound 13B. 1H NMR (400MHz, DMSO-d6) delta = 5.55 (br s, 1H), 3.87 (br d, J=7.9 Hz, 1H), 3.73 (br d, J=7.8 Hz, 1H), 3.63 - 3.51 (m, 2H), 2.90 (s, 1H), 2.59 (s, 1H), 1.36 (s, 9H).
13 g With palladium 10% on activated carbon; hydrogen; In ethanol; at 1650.0℃; To a solution oftert-butyl 3-hydroxy-3- (nitromethyl) azetidine-1-carboxylate (20g, 0.09 mol) in EtOH (200mL) was added Pd/C (2 g, 10%wt) and the reaction mixture was degassed under N 2 atmosphere for three times and stirred under H 2at 50 for 16 hrs. The mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by silica gel chromatography (DCM: MeOH = 50: 1) to give desired product (13.0g, 75%yield) as colorless oil. MS (ESI) m/z: 103 (M+H-100) +.

  • 3
  • [ 1008526-70-2 ]
  • [ 76-05-1 ]
  • C2HF3O2*C4H8N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; for 1.0h; EXAMPLE 722-(2-Fluoro-4-iodophenylamino)-3 -[3 -hydroxy- 3 -(nitromethyl)azetidin- 1 -ylcarbonyll - 5,5-dimethyl-4,5,6,7-tetrahydrothieno[2,3-c]azepin-8-one; Intermediate 33 (200 mg, 0.86 mmol) was dissolved in DCM (10 mL) and trifluoroacetic acid (1 mL) was added. The reaction mixture was stirred for 1 h and then the solvent and remaining acid were removed under vacuum at room temperature. The resulting salt was dissolved in DMF (8.3 mL) and Intermediate 5 (353 mg, 0.55 mmol) and triethylamine (317 muL) were added sequentially. The reaction was stirred for 18 h and the DMF was then removed under reduced pressure. A saturated aqueous solution of NaHCO3 was then added to the pale solid and the biphasic system was stirred for 1 h. The remaining solid was filtered, washed with further NaHCO3 (aq) and dried. This was then stirred in 50:50 MeCN/isopropyl ether, filtered once more and dried in a vacuum oven at 500C to yield the title compound (128 mg, 40%). deltaH (d6-DMSO) 8.71 (IH, s), <n="81"/>7.86 (IH, t, J 5.1 Hz), 7.67 (IH, dd, J 10.5, 1.9 Hz), 7.53-7.47 (IH, m), 7.08 (IH, t, J 8.7 Hz)5 6.48 (IH, s), 4.82 (2H, s), 4.16 (2H, d, J 10.2 Hz), 3.87 (2H, d, J 10.2 Hz), 2.86 (2H5 d, J5.1 Hz), 2.59 (2H, s), 0.96 (6H, s). LCMS (ES+) RT (pH 10) 2.32 minutes, 589 (M+H)+.
  • 4
  • [ 1008526-70-2 ]
  • C9H14N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With diethylamino-sulfur trifluoride; In dichloromethane; for 0.5h; Compound III-1 (20.0 g, 0.086 mol, 1.0 e.q.) was dissolved in 200 mL of DCM, and DAST (20.8 g, 0.129 mol, 1.5 e.q.) was added dropwise at 0 C.After the addition, the reaction was continued for 30 min. The TLC test showed that the reaction of the starting material was complete.Quench the reaction by adding 200 mL of water.Add saturated Na2CO3 aqueous solution with stirring to produce no bubbles.Dissolve and dry the organic phase with anhydrous sodium sulfate.Purified by sand column chromatography (PE: EA = 10/1).The compound I-1 was obtained as a white solid (14.9 g), yield 81%.
  • 5
  • [ 1008526-70-2 ]
  • 6-oxo-5-oxa-2,7-diazaspiro[3.4]octane-2-carboxylic acid tert-butyl ester [ No CAS ]
  • 6
  • [ 1008526-70-2 ]
  • tert-butyl 3-((2-chloroacetamido)methyl)-3-hydroxyazetidine-1-carboxylate [ No CAS ]
  • 7
  • [ 1008526-70-2 ]
  • tert-butyl 7-oxo-5-oxa-2,8-diazaspiro[3.5]nonane-2-carboxylate [ No CAS ]
  • 8
  • [ 1008526-70-2 ]
  • tert-butyl 5-oxa-2,8-diazaspiro[3.5]nonane-2-carboxylate [ No CAS ]
  • 9
  • [ 1008526-70-2 ]
  • tert-butyl 8-methyl-5-oxa-2,8-diazaspiro[3.5]nonane-2-carboxylate [ No CAS ]
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