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[ CAS No. 7529-22-8 ] {[proInfo.proName]}

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Chemical Structure| 7529-22-8
Chemical Structure| 7529-22-8
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Product Details of [ 7529-22-8 ]

CAS No. :7529-22-8 MDL No. :MFCD00005947
Formula : C5H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :LFTLOKWAGJYHHR-UHFFFAOYSA-N
M.W : 117.15 Pubchem ID :82029
Synonyms :

Calculated chemistry of [ 7529-22-8 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.3
TPSA : 38.66 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) : -7.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.49
Log Po/w (XLOGP3) : -0.58
Log Po/w (WLOGP) : -0.42
Log Po/w (MLOGP) : -2.07
Log Po/w (SILICOS-IT) : -0.06
Consensus Log Po/w : -0.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.2
Solubility : 73.8 mg/ml ; 0.63 mol/l
Class : Very soluble
Log S (Ali) : 0.24
Solubility : 203.0 mg/ml ; 1.73 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.55
Solubility : 33.4 mg/ml ; 0.285 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 7529-22-8 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P201-P202-P210-P240-P241-P280-P308+P313-P370+P378-P405-P501 UN#:1325
Hazard Statements:H228-H361 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7529-22-8 ]

* 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 [ 7529-22-8 ]
  • Downstream synthetic route of [ 7529-22-8 ]

[ 7529-22-8 ] Synthesis Path-Upstream   1~17

  • 1
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YieldReaction ConditionsOperation in experiment
98% With dihydrogen peroxide; benzonitrile In methanol; water at 65℃; for 0.5 h; The two-necked flask was charged with 0.22ml (2mmol) of N-methylmorpholine, 10mg of catalyst B and benzonitrile (2mmol) in 10ml of methanol. To the mixture was added dropwise 0.66ml (6 mmol) of a 30percent by weight of aqueous solution of hydrogen peroxide for a period of 15 minutes. The temperature is raised to 65 DEG C and continues the reaction for another 15 minutes. After the completion of the reaction (followed by TLC), the catalyst was filtered off and washed with methanol. To the filtrate a small amount of manganese dioxide was added to decompose the unreacted hydrogen peroxide. The treated reaction mixture was filtered to remove the solid MnO2 and concentrated under reduced pressure to obtain the product. The product thus obtained was purified by column chromatography to afford the corresponding amine oxide. N-methylmorpholine N-oxide of 98percent yield was obtained. This product is commercially available from Fluka, Aldrich, Lancaster and Merck companies
97% With dihydrogen peroxide; benzonitrile In methanol; water at 65℃; for 0.5 h; Oxidation of N-methylmorpholine using catalyst A, C, D, E and KO<t>Bu was carried out following the procedure as in example 2 and the results are given in Table 1.
97% With dihydrogen peroxide; benzonitrile In methanol; water at 65℃; for 0.5 h; Oxidation of N-methylmorpholine using catalyst A, C, D, E and KO<t>Bu was carried out following the procedure as in example 2 and the results are given in Table 1.
97% With dihydrogen peroxide; benzonitrile In methanol; water at 65℃; for 0.5 h; Oxidation of N-methylmorpholine using catalyst A, C, D, E and KO<t>Bu was carried out following the procedure as in example 2 and the results are given in Table 1.
96% With dihydrogen peroxide; benzonitrile In methanol; water at 65℃; for 0.5 h; Oxidation of N-methylmorpholine using catalyst A, C, D, E and KO<t>Bu was carried out following the procedure as in example 2 and the results are given in Table 1.
92% With dihydrogen peroxide; benzonitrile In water at 65℃; for 0.5 h; For recycle studies, a different protocol was adopted. After performing the reaction as stated above, the filtrate was siphoned out to obtain the product N-methylmorpholine N-oxide in 98percent yield by column chromatography. Fresh amounts of N-methylmorpholine (2mmol) and benzonitrile (2mmol) were charged into the flask containing used catalyst. To the mixture was added drop-wise 0.66ml (6 mmol) of a 30percent by weight of aqueous solution of hydrogen peroxide for a period of 15 minutes. The temperature was raised to 65 DEG C and continued the reaction for another 15 minutes. The protocol was adopted to obtain the product as well as to perform another recycle and the results were tabulated in the Table 1.; Examples 4-7[0044] The procedure was followed as in example 3 and the results are given in Table 1.
89% With dihydrogen peroxide; sodium hydrogencarbonate; trichloroacetonitrile In tetrahydrofuran; water at 0 - 25℃; for 4 h; General procedure: To a stirred solution of amine (1 mmol), trichloroacetonitrile (2 mmol), and NaHCO3 (0.5 mmol) inTHF (2 mL) was added an aqueous solution of 30percent (w/w) hydrogen peroxide(2 mmol, 0.2 mL) at 0 °C. The temperature was increased to 25 °C and the reaction continued. After completion of the reaction (monitored by TLC), the solvent was evaporated and MeCN (2 mL) was added. The mixture was cooled to 0 °C and filtered to remove the trichloroacetamide by-product. The filtrate was then concentrated under reduced pressure and purified by column chromatography. The products were identified by comparing their physical and spectral data with those of authentic samples reported in the literature.
75% With dihydrogen peroxide; benzonitrile In methanol; water at 65℃; for 1.1 h; Oxidation of N-methylmorpholine using catalyst A, C, D, E and KO<t>Bu was carried out following the procedure as in example 2 and the results are given in Table 1.

Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 21, p. 6498 - 6503
[2] Patent: EP1348692, 2003, A1, . Location in patent: Page/Page column 6-7
[3] Journal of the American Chemical Society, 2003, vol. 125, # 10, p. 2868 - 2869
[4] Patent: EP1348692, 2003, A1, . Location in patent: Page/Page column 7
[5] Patent: EP1348692, 2003, A1, . Location in patent: Page/Page column 7
[6] Patent: EP1348692, 2003, A1, . Location in patent: Page/Page column 7
[7] Chemical Communications, 2001, # 18, p. 1736 - 1737
[8] Patent: EP1348692, 2003, A1, . Location in patent: Page/Page column 7
[9] Chemistry - A European Journal, 2014, vol. 20, # 2, p. 559 - 563
[10] Patent: EP1348692, 2003, A1, . Location in patent: Page/Page column 6-7
[11] Tetrahedron Letters, 1980, vol. 21, p. 689 - 690
[12] Tetrahedron, 1994, vol. 50, # 42, p. 12185 - 12200
[13] Tetrahedron Letters, 2014, vol. 55, # 15, p. 2513 - 2516
[14] Chinese Journal of Catalysis, 2010, vol. 31, # 11-12, p. 1427 - 1432
[15] Journal of Organic Chemistry, 1998, vol. 63, # 19, p. 6650 - 6655
[16] Patent: EP1348692, 2003, A1, . Location in patent: Page/Page column 7
[17] Synthetic Communications, 1999, vol. 29, # 1, p. 11 - 14
[18] Chemical Communications, 2002, # 10, p. 1040 - 1041
[19] RSC Advances, 2016, vol. 6, # 75, p. 71550 - 71556
[20] Helvetica Chimica Acta, 1982, vol. 65, # 2, p. 521 - 537
[21] Journal of Organic Chemistry, 1985, vol. 50, # 9, p. 1563 - 1564
[22] Journal of Organic Chemistry, 1998, vol. 63, # 19, p. 6650 - 6655
[23] Tetrahedron Letters, 1981, vol. 22, # 46, p. 4591 - 4594
[24] Journal of the American Chemical Society, 1980, vol. 102, # 21, p. 6498 - 6503
[25] Tetrahedron, 1997, vol. 53, # 46, p. 15877 - 15888
[26] Journal of Organic Chemistry, 2002, vol. 67, # 24, p. 8400 - 8406
[27] Journal of Labelled Compounds and Radiopharmaceuticals, 2008, vol. 51, # 1, p. 28 - 32
[28] Magnetic Resonance in Chemistry, 2011, vol. 49, # 6, p. 320 - 327
[29] Magnetic Resonance in Chemistry, 2012, vol. 50, # 6, p. 415 - 423
[30] Chemistry - An Asian Journal, 2015, vol. 10, # 1, p. 133 - 138
[31] European Journal of Organic Chemistry, 2016, vol. 2016, # 20, p. 3401 - 3407
[32] Journal of Molecular Liquids, 2017, vol. 240, p. 233 - 239
[33] Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3999 - 4007
  • 2
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Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 10, p. 1939 - 1942
  • 3
  • [ 109-02-4 ]
  • [ 107743-45-3 ]
  • [ 7529-22-8 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 10, p. 1939 - 1942
  • 4
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  • [ 76847-41-1 ]
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Reference: [1] Tetrahedron Letters, 1981, vol. 22, # 46, p. 4591 - 4594
  • 5
  • [ 80866-75-7 ]
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  • [ 18515-67-8 ]
Reference: [1] Patent: US6593335, 2003, B1,
  • 6
  • [ 333389-49-4 ]
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  • [ 34841-47-9 ]
Reference: [1] Patent: US6214852, 2001, B1,
  • 7
  • [ 13726-69-7 ]
  • [ 7529-22-8 ]
  • [ 102195-80-2 ]
Reference: [1] Patent: WO2008/51404, 2008, A2, . Location in patent: Page/Page column 106
  • 8
  • [ 114615-82-6 ]
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  • [ 95656-88-5 ]
  • [ 130312-02-6 ]
Reference: [1] Patent: US6331545, 2001, B1,
  • 9
  • [ 114615-82-6 ]
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  • [ 98977-36-7 ]
Reference: [1] Patent: US2004/19058, 2004, A1,
  • 10
  • [ 13726-69-7 ]
  • [ 7529-22-8 ]
  • [ 166410-05-5 ]
YieldReaction ConditionsOperation in experiment
61% With tetrapropylammonium perruthennate In hexane; dichloromethane; ethyl acetate EXAMPLE 5 STR11 Step A: 1-(tert-Butyloxycarbonyl)-4-oxo-L-Proline tert-Butyl Ester
To a solution of (4R)-1-(tert-butyloxycarbonyl)-4-hydroxy-L-proline (1.0 g, 3.48 mmol) in dichloromethane (3 mL) was added 4-methylmorpholine N-oxide (612 mg, 5.22 mmol) followed by 4 A powdered molecular sieves (1.74 g) and tetrapropylammonium perruthenate(VII) (TPAP) (61 mg, 0.174 mmol).
After stirring for 1 hour at room temperature, an additional 30 mg of TPAP was added, and the reaction was continued for 2 hours.
The reaction mixture was applied to a column of silica gel (packed in 20percent ethyl acetate/hexane).
Elution with the same mobile phase afforded pure ketone as a white crystalline solid; yield 610 mg (61percent).
400 MHz 1 H-NMR (CDCl3): δ1.43 (s, 9H); 1.47 (s, 9H); 2.50 (dd, 1H); 2.89 (m, 1H); 3.82-3.93 (m, 2H); 4.60 (dd, 1H).
Reference: [1] Patent: US5821261, 1998, A,
  • 11
  • [ 4606-65-9 ]
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  • [ 24424-99-5 ]
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  • [ 118156-93-7 ]
Reference: [1] Patent: US2004/19058, 2004, A1,
  • 12
  • [ 7529-22-8 ]
  • [ 116574-71-1 ]
  • [ 118156-93-7 ]
Reference: [1] Patent: US6331545, 2001, B1,
  • 13
  • [ 224309-64-2 ]
  • [ 114615-82-6 ]
  • [ 7529-22-8 ]
  • [ 179321-49-4 ]
Reference: [1] Patent: US2004/19058, 2004, A1,
  • 14
  • [ 114615-82-6 ]
  • [ 24424-99-5 ]
  • [ 27489-62-9 ]
  • [ 50910-54-8 ]
  • [ 7529-22-8 ]
  • [ 179321-49-4 ]
Reference: [1] Patent: US2004/19058, 2004, A1,
  • 15
  • [ 114615-82-6 ]
  • [ 7529-22-8 ]
  • [ 127406-55-7 ]
Reference: [1] Patent: US5985901, 1999, A,
[2] Patent: US6156772, 2000, A,
  • 16
  • [ 1229236-80-9 ]
  • [ 7529-22-8 ]
  • [ 1229236-83-2 ]
YieldReaction ConditionsOperation in experiment
66.25% at 23 - 40℃; for 50.5 h; Inert atmosphere PREPARATION 14
(4-chloro-2-fluorophenyl)(6-chloro-2-methyl-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-3-yl)methanone
Add ethanol (12 L), (4-chloro-2-fluorophenyl)(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)methanone (897.70 g, 2.77 mol) and bis (2,4-pentanedionato)oxovanadium (IV) (146.81 g, 553.67 mmol) to a reaction vessel with a nitrogen atmosphere.
Add an ethanol (6 L) solution of 4-methylmorpholine 4-oxide (3.89 kg, 33.21 mol) drop-wise over 150 min keeping the reaction temperature at 23-33° C.; then heat the reaction at 40° C. for 48 h.
Cool the reaction and concentrate by removal of solvent (13 L).
Filter the resulting mixture, rinse the filter cake with hexane (1 L) and then dry. (728 g, 66.25percent; mp 145-147° C.; M+=423).
Reference: [1] Patent: US2010/152181, 2010, A1, . Location in patent: Page/Page column 4
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  • [ 1229236-83-2 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 1, p. 70 - 81
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