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[ CAS No. 101376-26-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 101376-26-5
Chemical Structure| 101376-26-5
Chemical Structure| 101376-26-5
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Product Details of [ 101376-26-5 ]

CAS No. :101376-26-5 MDL No. :MFCD06799481
Formula : C12H17NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CPLXVETYMUMERG-GFCCVEGCSA-N
M.W : 207.27 Pubchem ID :1514271
Synonyms :

Calculated chemistry of [ 101376-26-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.39
TPSA : 32.7 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) : -7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 0.77
Log Po/w (WLOGP) : 0.35
Log Po/w (MLOGP) : 0.86
Log Po/w (SILICOS-IT) : 1.72
Consensus Log Po/w : 1.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.71
Solubility : 4.06 mg/ml ; 0.0196 mol/l
Class : Very soluble
Log S (Ali) : -1.04
Solubility : 19.0 mg/ml ; 0.0918 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.529 mg/ml ; 0.00255 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 101376-26-5 ]

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 [ 101376-26-5 ]

* 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.

  • Upstream synthesis route of [ 101376-26-5 ]
  • Downstream synthetic route of [ 101376-26-5 ]

[ 101376-26-5 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 106973-37-9 ]
  • [ 101376-26-5 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With borane-THF In tetrahydrofuran at 20℃; for 6 h;
Stage #2: With methanol In tetrahydrofuran at 80℃; for 2 h;
Intermediate 65(R)-(4-Benzylmorpholin-3-yl)methanol[0351][Chemical Formula 96]To a solution of intermediate 66 (12.6 g, 53.6 mmol) in tetrahydrofuran (200 mL) was added borane-tetrahydrofuran-complex (1.0 M, 348 mL). After stirring for 6 hours at room temperature, to the mixture was added methanol, and after heated to 80°C, stirred for 2 hours. To the mixture were added saturated sodium bicarbonate water and ethyl acetate, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified with silica gel column (hexane/ethyl acetate = 90/10 to 10/90) to give the title compound (9.60 g, 46.0 mmol, 86percent).MS (ESI+) 208 (IVT+l, 100percent)
Reference: [1] Patent: WO2011/111875, 2011, A1, . Location in patent: Page/Page column 90-91
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2577 - 2580
[3] Helvetica Chimica Acta, 2004, vol. 87, # 1, p. 90 - 105
  • 2
  • [ 211053-49-5 ]
  • [ 100-39-0 ]
  • [ 101376-26-5 ]
YieldReaction ConditionsOperation in experiment
89% With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 2 h; Benzyl bromide (1.2 g, 7.06 mmol) was added in one portion to a stirred solution of (R)- morpholin-3-ylmethanol (986 mg, 6.42 mmol) and DIPEA (1.66 g, 12.8 mmol) in MeCN (50 ml) and the resulting solution was stirred at rt for 2h, whereafter the mixture was then concentrated under reduced pressure. The afforded residue was dissolved in DCM (50ml) was and washed sequentially with sat. aq. NaHC03 (50 ml) and 1 M KOH (10 ml). The aqueous phase was extracted with DCM (25 ml) and the combined organic layers were dried over Na2S04, filtered and concentrated which gave the title compound (1.19 g, 89percent). MS (ESI): 208 [M+H]+.
Reference: [1] Patent: WO2013/95275, 2013, A1, . Location in patent: Page/Page column 48; 49
  • 3
  • [ 106973-40-4 ]
  • [ 101376-26-5 ]
Reference: [1] Helvetica Chimica Acta, 2004, vol. 87, # 1, p. 90 - 105
  • 4
  • [ 714971-27-4 ]
  • [ 101376-26-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6527 - 6530
  • 5
  • [ 106910-76-3 ]
  • [ 101376-26-5 ]
Reference: [1] Helvetica Chimica Acta, 2004, vol. 87, # 1, p. 90 - 105
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2577 - 2580
[3] Patent: WO2011/111875, 2011, A1,
  • 6
  • [ 100-52-7 ]
  • [ 101376-26-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2577 - 2580
  • 7
  • [ 101376-26-5 ]
  • [ 211053-49-5 ]
YieldReaction ConditionsOperation in experiment
57%
Stage #1: With hydrogen; acetic acid In ethanol at 20℃;
Stage #2: With ammonia In methanol
(a) (3R)-Morpholin-3-ylmethanol; A solution of [(3i?)-4-benzylmorpholin-3-yl]methanol (see J. Med. Chem.; 29; 1986; 1288- 1290; 1.1 g, 5.4 mmol) in ethanol (25 mL) was mixed with palladium hydroxide (20percent on carbon, 0.7 g) and acetic acid (0.5 mL). The mixture was stirred under hydrogen overnight20 at 1.2 bar and RT. The catalyst was filtered off and the solvent was removed by evaporation. The residue (except 200 mg) was dissolved in ether (1 mL) and THF (10 mL). The solution was filtered through a strong cation exchange column (Isolute SCX-2, 10 g). The column was washed with THF and then the product was eluted with ammonia- saturated methanol. The solvent was removed by evaporation and there was obtained 0.3625 g (57percent) of (3i?)-morpholin-3-ylmethanol as an oil. 1H NMR (500 MHz, CD3OD): 2.9 (m, 3H), 3.3 (t, IH)5 3.5 (m, 3H), 3.7-3.9 (m, 2H).
Reference: [1] Patent: WO2006/137790, 2006, A1, . Location in patent: Page/Page column 35
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2227 - 2244
  • 8
  • [ 101376-26-5 ]
  • [ 696582-88-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2227 - 2244
  • 9
  • [ 101376-26-5 ]
  • [ 917572-28-2 ]
YieldReaction ConditionsOperation in experiment
94% With thionyl chloride In dichloromethane for 2.5 h; Heating / reflux (a) (3S)-4-Benzyl-3-(chloromethyl)morpholine; To a solution of [(3i?)-4-benzykcιorpholin-3-yl]methanol (see J. Med. Chem.; 29; 1986; 0 1288-1290; 1.83 g, 8.8 mmol) in dry methylene chloride (15 mL) was added thionyl chloride (3.15 g, 26.5 mmol) and DMF (2 drops). The mixture was heated to reflux for 2 h 30 min and then the solvent was removed by evaporation. The residue was treated with aqueous NaHCO3 and the solution was extracted with ethyl acetate. The organic solution was separated and the solvent was removed by evaporation. There was obtained 1.88 g s (94percent) of (31S)-4-benzyl-3-(chloromethyl)morpholine as an oil. 1H NMR (500 MHz, CDCl3): 2.3-2.4 (m, IH), 2.7 (m, IH), 2.8 (m, IH), 3.5 (d, IH), 3.6-3.9 (m, 5H), 4.0 (d, IH), 7.3 (m, IH), 7.4 (m, 4H); LCMS: m/z 226 (M+l)+.
94% With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 2.5 h; Heating / reflux (a) (3S)-4-Benzyl-3-(chloromethyl)morpholineTo a solution of [(3i?)-4-benzylmorpholin-3-yl]methanol (see J. Med. Chem.; 29; 1986; 1288-1290; 1.83 g, 8.8 mmol) in dry methylene chloride (15 mL) was added thionyl chloride (3.15 g, 26.5 mmol) and DMF (2 drops). The mixture was heated to refluxed for 2 h 30 min and then the solvent was removed by evaporation. The residue was treated with aqueous NaHCO3 and the solution was extracted with ethyl acetate. The organic solution was separated and the solvent was removed by evaporation. There was obtained 1.88 g (94percent) of (3S)-4-berLzyl-3-(chloromethyl)morpholine as an oil. 1H NMR (500 MHz, CDCl3): 2.3-2.4 (m, IH), 2.7 (m, IH), 2.8 (m, IH), 3.5 (d, IH), 3.6-3.9 (m, 5H), 4.0 (d, IH), 7.3 (m, IH), 7.4 (m, 4H); LCMS: m/z 226 (M+l)+.
Reference: [1] Patent: WO2006/137790, 2006, A1, . Location in patent: Page/Page column 32
[2] Patent: WO2006/137791, 2006, A1, . Location in patent: Page/Page column 43
[3] Patent: WO2011/111875, 2011, A1, . Location in patent: Page/Page column 90
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2227 - 2244
  • 10
  • [ 24424-99-5 ]
  • [ 101376-26-5 ]
  • [ 215917-99-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6527 - 6530
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