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Chemical Structure| 174649-09-3
Chemical Structure| 174649-09-3
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Product Details of [ 174649-09-3 ]

CAS No. :174649-09-3 MDL No. :MFCD18070719
Formula : C15H19FN2O6S Boiling Point : -
Linear Structure Formula :- InChI Key :UCVIKCGVGWBTTI-GFCCVEGCSA-N
M.W : 374.39 Pubchem ID :10643120
Synonyms :

Calculated chemistry of [ 174649-09-3 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.53
Num. rotatable bonds : 5
Num. H-bond acceptors : 7.0
Num. H-bond donors : 0.0
Molar Refractivity : 93.3
TPSA : 93.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.59
Log Po/w (XLOGP3) : 0.8
Log Po/w (WLOGP) : 1.7
Log Po/w (MLOGP) : 1.09
Log Po/w (SILICOS-IT) : 0.5
Consensus Log Po/w : 1.34

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.51
Solubility : 1.15 mg/ml ; 0.00307 mol/l
Class : Soluble
Log S (Ali) : -2.35
Solubility : 1.67 mg/ml ; 0.00446 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.83
Solubility : 0.555 mg/ml ; 0.00148 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.69

Safety of [ 174649-09-3 ]

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 [ 174649-09-3 ]

* 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 [ 174649-09-3 ]
  • Downstream synthetic route of [ 174649-09-3 ]

[ 174649-09-3 ] Synthesis Path-Upstream   1~14

  • 1
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YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0℃; for 0.5 h; To a solution of 132.8 g of (R)-N-[[3-[3-fluoro-4-morpholinyl]phenyl]-2-oxo-5- oxazolidinyl] methanol and 87.1 g of triethylamine in IL of methylene dichloride at O0C under nitrogen was added 74 gm of methanesulfonyl chloride. The reaction mixture was allowed to stir at 0°C for 30 min, then allowed to warm to ambient temperature. A white solid was precipitated. 1.75 L water, 6.50 L methylene dichloride and IL ethyl acetate mixture were added followed by stirring for 30 min. The reaction mass was filtered to get a white solid. Yield: 140 g.; Percentage: 105.42percent w/w
96% With triethylamine In tetrahydrofuran at 8 - 15℃; for 3.75 h; Cooling with ice; Inert atmosphere Example 1
Preparation of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxazolidin-5-yl)methyl methanesulfonate (compound (V) with R2 = methyl)
To a solution of ((R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methanol (20 g, 67.5 mmol) in tetrahydrofuran (220 mL, 11 mL/g) at room temperature under inert atmosphere was added triethylamine (12.2 mL, 87.8 mmol, 1.3 eq).
The mixture was cooled in an ice bath and methanesulfonyl chloride (6.8 mL, 87.8 mmol, 1.3 eq) was added dropwise over approximately 15 min (resulting in an increase in Tint from 8 to 15 °C.
A pale lilac precipitate forms immediately).
The ice bath is removed and the suspension is stirred for 3.5 h.
The suspension was filtered at room temperature and the solids (32.9 g) were suspended in water (165 mL, 5 vol) and stirred for 2 h at room temperature.
The suspension was filtered and a second suspension in water was carried out (as above).
The suspension was filtered and the collected solids were dried in-vacuo (60 °C, 2-4 mm Hg) to give ((R)-3-(3-fluoro-4-morpholinophenyl)-2-oxazolidin-5-yl)methyl methanesulfonate (24.4 g, 96percent) as a pale lilac powder.
1H NMR (400 MHz, acetone-d6): δ 7.57 (dd, 1H, ArH, J 2.8 and 15 Hz), 7.23 (ddd, 1H, ArH, J 2.7 and 9 Hz), 7.07 (t, 1H, ArH, J 9Hz), 5.05-5.01 (m, 1H, CH), 4.58 (qd, 2H, CH2, J 3, 5, 8.5 and 12 Hz), 4.30 (t, 1H, CH, J 9 Hz), 3.99 (dd, 1H, CH, J 6 and 9 Hz), 3.79-3.77 (m, 4H, CH2), 3.20 (s, 3H, CH3), 3.03-3.01 (m, 4H, CH2) ppm.
Mp 178.7 - 180.6 °C
[α]D-55.5° (c 0.98, acetone)
95% With triethylamine In dichloromethane at 20 - 30℃; (R)-[N-3-(3-Fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl] methyl methane sulfonate[134] Triethyl amine (68.2g), Methane sulfonyl chloride (48.3g) are added to a flaskcontaining Dichloromethane (1900ml) and(R)-[N-3-(3-Fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl] methanol (lOOg) at 20-30°C with constant stirring for 2-3 hours. After cooling filtration wash the solid with Dichloromethane followed by water wash dried in air tray dryer. Yield: 1.20.: Percentage 95 w/w.[135]
90% With triethylamine In dichloromethane at 0 - 40℃; Example-1: Preparation of (5R)-(N)-[[3-fluoro-(4-morpholinylphenyl)-2-oxo-5-oxazolidinyl] methyl] sulphonate.(5R)-(N)-[3-fluoro-(4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methanol (1 mole eq, 100 g) was taken in 600 ml methylene dichloride and cooled to 0-50C, to it was added triethylamine 1.92 mol eq, 90.2 ml). The reaction mixture was stirred to 10-15mins followed by the addition of methanesulfonyl chloride (1.44 mole eq, 37.5ml) at the same temperature. The temperature of the reaction mixture was raised to room temperature and further to 400C with continuous stirring for 7 - 8 hours. The reaction mixture was quenched with water and stirred for lhr at room temperature, filtered, washed with methylene dichloride and dried to obtain the titled compound (Yield : 90percent).
73% With triethylamine In dichloromethane at 0 - 20℃; for 10 h; Example-8: Preparation of (R)-[[N-3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5- oxazolidinyljmethyl] 4-methylmethanesulfonate (IX)(R)-[N-3-(3-fluoro-4-mo holinylphenyl)-2- oxo-5-oxazolidinyl] methanol (6.5 g) and methanesulfonyl chloride (3.78 g) were dissolved in DCM (60 ml). The resulting solution was cooled to 0-5°C and to the cold solution; triethylamine (3.76 g) was added. The obtained solution was warmed to room temperature and stirred for lOh. After the completion of reaction, it was concentrated. In the resulting reaction mass, water (50 ml) was added and stirred at 50-55°C for lh and further at 25-30°C for next lh. The solid obtained was filtered, washed with water and suck dried. The suck dried material was suspended in methanol (65 ml) and heated to 60°C. The suspension was stirred at 55-60°C for 2h and further at room temperature for lh. The solid was filtered, washed with methanol at room temperature and dried to obtain the titled compound (6 g) with 73percent yield.
95 g With triethylamine In dichloromethane at 45℃; ExampIe-3: (R)-fN-f3-(3-fluoro-4-morphoIinylphenylV-2-oxo-5- oxazolidinyll methyl] methane sulfonateTo a solution of 100 g of N-carbobenzyloxy-3-fluoro-4-morpholinyl aniline in 500 mL of freshly distilled tetrahydrofuran at -80°C under nitrogen, was added 105 mL of n-butyl lithium/hexane via syringe within 90 minutes, and the mixture stirred for 60 minutes. Further, a solution of 45.9 g of (R)-glycidylbutyrate in 80 mL of tetrahydrofuran was added within 90 minutes, and stirred for 60 minutes. The reaction mixture was removed from the dry ice bath, and allowed to come to ambient temperature. After stirring for 4-6 hours, the reaction mixture was quenched in 134 g of saturated aqueous ammonium chloride solution, followed by 500 mL of toluene, and the aqueous layer extracted with toluene. The combined organic layers were washed with 360 mL of brine. The organic layer was treated with 4 g activated charcoal and stirred for 30 minute and filtered. The filtrate was concentrated under vacuum at 60°C to remove toluene completely. In the mixture of residue of (R)-N-[[3-[3-fluoro-4- moφholinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol, 300 mL methylene dichloride and 46 g triethylamine mixture was added within 90 minutes. The reaction mixture was warmed to 45°C and stirred for 3 hours. Methylene dichloride was removed under vacuum below 50°C and the residue was cooled to room temperature. The residue were triturated with 500 mL of toluene and stirred for 1 hour and filtered. The wet-cake was washed with toluene and slurried in water for 1 hour. The solid was filtered and washed with water. The product dried at 60°C to 65°C to get 95 g (84percent) of (R)-[N-[3-(3- fluoro-4-mo holinylphenyl)-2-oxo-5-oxazolidinyl]methyl]methane sulfonate.
40 g With triethylamine In dichloromethane at 0 - 5℃; for 0.5 h; (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol (50 gr) and triethylamine (42.6 gr) in methylene dichloride (250 ml) was cooled in ice-bath and treated with methane sulphonyl chloride (38.2 gr).
The mixture was stirred for 30 min at 0-5° C.
The precipitated product is filtered and washed with chilled DM water (250 ml).
Dried the material at 50-55° C. to give 40 gr of (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methyl methanesulphonate.
122 g With triethylamine In dichloromethane at 0 - 5℃; III.
Preparation of (R)-N-[[3-(3-fluoro-4-morpholinyl)phenyl]-2-oxo-5- oxazolidinyljmethansulfonate:
Dichloromethane (1800.0ml), f )-N-[[3-(3-fluoro-4-moφholinyl)phenyl]-2-oxo-5- oxazolidinyljmethanol (100. Ogm), triethyl amine (68.45gm) were charged into RBF at 25- 30°C and cooled to 0-5°C. A solution of methane sulphonyl chloride (53.78gm) and in MDC (200.0ml) was added slowly for a period of 25-30 minutes to the reaction mass at 0- 5°C and stirred for 2 hours. After reaction completion, the reaction mass was concentrated to thick slurry under vacuum at 35-40°C and then chased with water (200.0 ml) at 35-40°C to remove traces of dichloromethane. Water (800.0ml) was charged to the reaction mass at 35-40°C, cooled to 25-30°C and stirred for 30 minutes. The suspension was filtered, washed the solid with water (2x250.0ml) followed by with methanol (100.0ml) and suck dried. The wet solid was stirred in methanol (200.0 ml) for 30 minutes at 25-30°C, filtered the solid and washed with methanol (2x100.0ml) and then suck dried. The obtained solid was dried in an air oven at 25-30°C for 30 minutes followed by at 45-50°C to afford titled compound

Reference: [1] Patent: WO2009/63505, 2009, A2, . Location in patent: Page/Page column 14
[2] Patent: EP2163547, 2010, A1, . Location in patent: Page/Page column 8
[3] Patent: WO2011/77310, 2011, A1, . Location in patent: Page/Page column 12; 13
[4] Synthetic Communications, 2010, vol. 40, # 6, p. 789 - 798
[5] Patent: WO2010/84514, 2010, A2, . Location in patent: Page/Page column 15
[6] Patent: WO2011/114210, 2011, A2, . Location in patent: Page/Page column 23
[7] J. Med. Chem., 1996, vol. 39, # 3, p. 673 - 679
[8] Tetrahedron Letters, 1999, vol. 40, # 26, p. 4855 - 4856
[9] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 4, p. 353 - 360
[10] Tetrahedron Letters, 2006, vol. 47, # 38, p. 6799 - 6802
[11] European Journal of Medicinal Chemistry, 2009, vol. 44, # 8, p. 3217 - 3227
[12] Organic and Biomolecular Chemistry, 2008, vol. 6, # 24, p. 4634 - 4642
[13] Patent: WO2012/114355, 2012, A1, . Location in patent: Page/Page column 11
[14] Patent: WO2013/72923, 2013, A1, . Location in patent: Page/Page column 16-17
[15] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 779 - 785
[16] Patent: US2013/324719, 2013, A1, . Location in patent: Paragraph 0022; 0056-0057
[17] Patent: WO2015/68121, 2015, A1, . Location in patent: Page/Page column 15
[18] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 120 - 131
  • 2
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Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 4, p. 353 - 360
[2] J. Med. Chem., 1996, vol. 39, # 3, p. 673 - 679
[3] Patent: WO2011/77310, 2011, A1,
[4] Patent: WO2011/114210, 2011, A2,
[5] Patent: WO2011/114210, 2011, A2,
[6] Patent: WO2012/114355, 2012, A1,
[7] Patent: WO2013/72923, 2013, A1,
[8] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 779 - 785
[9] Patent: US2013/324719, 2013, A1,
[10] Patent: WO2015/68121, 2015, A1,
[11] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 120 - 131
  • 3
  • [ 2689-39-6 ]
  • [ 174649-09-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 4, p. 353 - 360
[2] J. Med. Chem., 1996, vol. 39, # 3, p. 673 - 679
[3] Patent: WO2011/77310, 2011, A1,
[4] Patent: WO2011/114210, 2011, A2,
[5] Patent: WO2011/114210, 2011, A2,
[6] Patent: WO2012/114355, 2012, A1,
[7] Patent: WO2013/72923, 2013, A1,
[8] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 779 - 785
[9] Patent: US2013/324719, 2013, A1,
[10] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 120 - 131
  • 4
  • [ 93246-53-8 ]
  • [ 174649-09-3 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 38, p. 6799 - 6802
[2] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 4, p. 353 - 360
[3] J. Med. Chem., 1996, vol. 39, # 3, p. 673 - 679
[4] Patent: WO2011/77310, 2011, A1,
[5] Patent: WO2011/114210, 2011, A2,
[6] Patent: WO2011/114210, 2011, A2,
[7] Patent: WO2012/114355, 2012, A1,
[8] Patent: WO2013/72923, 2013, A1,
[9] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 779 - 785
[10] Patent: US2013/324719, 2013, A1,
[11] Patent: WO2015/68121, 2015, A1,
[12] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 120 - 131
  • 5
  • [ 168828-81-7 ]
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Reference: [1] J. Med. Chem., 1996, vol. 39, # 3, p. 673 - 679
[2] Patent: WO2011/77310, 2011, A1,
[3] Patent: WO2011/114210, 2011, A2,
[4] Patent: WO2013/72923, 2013, A1,
[5] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 779 - 785
[6] Patent: WO2015/68121, 2015, A1,
[7] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 120 - 131
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Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 38, p. 6799 - 6802
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Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 38, p. 6799 - 6802
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Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 38, p. 6799 - 6802
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Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 26, p. 4855 - 4856
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Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 26, p. 4855 - 4856
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Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 26, p. 4855 - 4856
  • 12
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Reference: [1] Patent: WO2012/114355, 2012, A1,
[2] Patent: US2013/324719, 2013, A1,
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Reference: [1] Patent: WO2012/114355, 2012, A1,
[2] Patent: US2013/324719, 2013, A1,
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Reference: [1] Patent: WO2011/114210, 2011, A2,
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Chemical Structure| 444335-16-4

[ 444335-16-4 ]

(R)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

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