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[ CAS No. 897019-55-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 897019-55-5
Chemical Structure| 897019-55-5
Structure of 897019-55-5 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 897019-55-5 ]

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Product Details of [ 897019-55-5 ]

CAS No. :897019-55-5 MDL No. :MFCD06804557
Formula : C6H14ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :FWEILSWQALGJKN-UHFFFAOYSA-N
M.W : 151.63 Pubchem ID :53407805
Synonyms :

Calculated chemistry of [ 897019-55-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.61
TPSA : 21.26 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.18
Log Po/w (WLOGP) : 0.81
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 1.1
Consensus Log Po/w : 0.73

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.33
Solubility : 7.17 mg/ml ; 0.0473 mol/l
Class : Very soluble
Log S (Ali) : -1.22
Solubility : 9.09 mg/ml ; 0.06 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.41
Solubility : 5.86 mg/ml ; 0.0386 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.44

Safety of [ 897019-55-5 ]

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

Application In Synthesis of [ 897019-55-5 ]

* 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 [ 897019-55-5 ]

[ 897019-55-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 832753-56-7 ]
  • [ 897019-55-5 ]
  • ((3-(4-chlorophenyl)-4-(2-oxopyrrolidin-1-yl)-4,5-dihydro-1H-pyrazol-1-yl)(3-propoxyazetidin-1-yl)methylene)-cyanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;
  • 2
  • [ 897019-47-5 ]
  • [ 897019-55-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-diphenylmethyl-3-propoxy-azetidine With carbonochloridic acid 1-chloro-ethyl ester In 1,2-dichloro-ethane at 70℃; for 1.5h; Stage #2: With methanol In 1,2-dichloro-ethane at 20 - 70℃; for 1.5h;
  • 3
  • [ 897019-55-5 ]
  • [ 1323408-85-0 ]
  • (S)-3-(1-oxo-4-((4-((3-propoxyazetidin-1-yl)methyl)benzyl)oxy)isoindolin-2-yl)piperidine-2,6-dione hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% Stage #1: 3-propoxyazetidine hydrochloride; (S)-3-(4-(4-(bromomethyl)benzyloxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione With N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 50℃; for 3.5h; Stage #2: With hydrogenchloride In water 5.96 5.96 3-(1-OXO-4-((4-((3-PROPOXYAZETIDIN-1-YL)METHYL)BENZYL) OXY)ISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE HYDROCHLORIDE To a solution of (S)-3-(4-(4-(bromomethyl)benzyloxy)-1-oxoisoindolin-2-yl)piperidine-2,6-dione (200 mg, 0.451 mmol) in dry MeCN (5 mL), was added 3-propoxyazetidine hydrochloride (75 mg, 0.496 mmol) and DIEA (0.276 mL, 1.579 mmol). The mixture was stirred at room temperature for 3 h and LCMS indicated benzyl bromide starting material was consumed. The mixture was heated to 50° C. for ~30 min, cooled slowly to rt, and then stored at 4° C. overnight. The mixture containing the crude product was concentrated in vacuo and the residue was dissolved in minimal DMF (~5 mL) for Prep HPLC purification. The product was eluted with an acetonitrile/water gradient (0.1% formic acid in both mobile phases, 5% to 60% MeCN over 20 minutes) and fractions were collected by mass trigger. The desired fractions were combined and concentrated in vacuo to give a clear glass residue. 1N HCl (2-3 mL) was added and the mixture was concentrated in vacuo to dryness. This process was repeated twice to obtain HCl salt. To the clear residue, MeCN and Et2O were added in small portions and the mixture was sonicated until a white solid was obtained. The slurry was concentrated in vacuo to dryness and twice evaporated from Et2O (3-4 mL portions) until a free flowing white solid was obtained. The solid was dried in a vacuum oven overnight to give 3-(1-oxo-4-((4-((3-propoxyazetidin-1-yl)methyl)benzyl)oxy)isoindolin-2-yl)piperidine-2,6-dione hydrochloride as a white solid (52 mg, 22%): HPLC: Waters Symmetry C18, 5 μm, 3.9*150 mm, 1 ml/min, 240 nm, 20/80 CH3CN/0.1% H3PO4, 6.60 min (99.8%); mp: 142-144° C.; 1H NMR (DMSO-d6) δ 0.87 (t, J=7.4 Hz, 3H, CH3), 1.40-1.59 (m, 2H, CH2), 1.91-2.06 (m, 1H, CHH), 2.35-2.47 (m, 1H, CHH), 2.53-2.65 (m, 1H, CHH), 2.84-3.01 (m, 1H, CHH), 3.28-3.39 (m, 2H, CH2O, overlapped with DMSO), 3.89 (br. s., 2H, CH2), 4.06-4.23 (m, 2H, CH2), 4.23-4.32 (m, 2H, CHH, CHH), 4.36 (s, 2H, CH2), 4.44 (d, J=17.6 Hz, 1H, CHH), 5.12 (dd, J=5.1, 13.2 Hz, 1H, CH), 5.28 (s, 2H, CH2), 7.27-7.38 (m, 2H, Ar), 7.44-7.53 (m, 1H, Ar), 7.55 (s, 4H, Ar), 10.97 (s, 1H, NH), 11.09 (br. s., 1H, HCl); 13C NMR (DMSO-d6) δ -0.01, 12.34, 24.22, 32.97, 47.32, 53.70, 62.70, 63.30, 69.33, 71.21, 71.67, 117.13, 117.29, 129.67, 130.77, 131.82, 131.96, 134.99, 137.66, 138.23, 155.27, 170.35, 172.81, 174.98; LCMS: MH=478; Anal Calcd for C27H31N3O5.+3.2 H2O+1.3 HCl: C, 55.66; H, 6.70; N, 7.21; Cl, 7.91; H2O, 9.89; Found: C, 53.73; H, 6.33; N, 6.90; Cl, 7.63; H2O, 9.62.
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Reason: Free-salt