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[ CAS No. 4045-25-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 4045-25-4
Chemical Structure| 4045-25-4
Structure of 4045-25-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4045-25-4 ]

CAS No. :4045-25-4 MDL No. :MFCD06800959
Formula : C6H14ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :DMFJRRMECZFOKR-UHFFFAOYSA-N
M.W : 151.63 Pubchem ID :11542813
Synonyms :

Calculated chemistry of [ 4045-25-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
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) : -6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.0
Log Po/w (WLOGP) : 0.81
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 1.1
Consensus Log Po/w : 0.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.34
Solubility : 6.87 mg/ml ; 0.0453 mol/l
Class : Very soluble
Log S (Ali) : -1.04
Solubility : 14.0 mg/ml ; 0.0922 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.16
Solubility : 10.5 mg/ml ; 0.069 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.01

Safety of [ 4045-25-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4045-25-4 ]

* 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 [ 4045-25-4 ]
  • Downstream synthetic route of [ 4045-25-4 ]

[ 4045-25-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 4045-25-4 ]
  • [ 4045-24-3 ]
Reference: [1] Patent: WO2006/104406, 2006, A1, . Location in patent: Page/Page column 167
  • 2
  • [ 188622-27-7 ]
  • [ 4045-25-4 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride In 1,4-dioxane at 0 - 23℃; for 2 h; Step-3: Preparation of intermediate-41a; To a stirred solution of intermediate 40a (810 mg, 3.76 mmol) in 1,4-dioxane (5 mL) was added 4M HCl in 1,4-dioxane (8 mL) at 0° C. The reaction mass was stirred for 2 h at 23° C. The organics were evaporated off under reduced pressured. The residue was washed with dry ether and dried under vacuum to afford intermediate 41a (430 mg, >99percent) as its HCl salt.
Reference: [1] Patent: US2011/92475, 2011, A1, . Location in patent: Page/Page column 18
[2] Patent: WO2006/64196, 2006, A1, . Location in patent: Page/Page column 138-139
[3] Patent: US2005/261291, 2005, A1, . Location in patent: Page/Page column 67
[4] Patent: US6194409, 2001, B1,
[5] Patent: EP1621537, 2006, A1, . Location in patent: Page/Page column 52
[6] Patent: EP1762568, 2007, A1, . Location in patent: Page/Page column 46
[7] Patent: EP1785418, 2007, A1, . Location in patent: Page/Page column 44
[8] Patent: EP1803719, 2007, A1, . Location in patent: Page/Page column 26
[9] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 56
[10] Patent: WO2006/104406, 2006, A1, . Location in patent: Page/Page column 167
  • 3
  • [ 5382-16-1 ]
  • [ 74-88-4 ]
  • [ 4045-25-4 ]
YieldReaction ConditionsOperation in experiment
33%
Stage #1: With t-butyl malonate In acetonitrile for 20 h;
Stage #2: With sodium hydride In acetonitrile; mineral oil at 0 - 25℃; for 20.5 h;
Stage #3: With hydrogenchloride In 1,4-dioxane at 25℃; for 20 h;
EXAMPLE 93A/-methyl-4-[4-(methyloxy)-1 -piperidinyl]-3-(1 /-/-purin-6-ylamino)benzenesulfonamidea) 4-(methyloxy)piperidine hydrochlori To a solution of 4-piperidinol (500 mg, 4.94 mmol) in CH3CN (20 mL) was added Boc20 (1.15 mL, 4.94 mmol). The mixture was stirred for 20 h and concentrated to afford a colorless oil, which was dissolved in anhydrous THF (20 mL). The solution was cooled to 0 °C and treated with NaH (60percent dispersion in oil, 29 mg, 7.41 mmol). The mixture was gradually warmed to rt. After stirring at rt for 0.5 h, iodomethane (1403 mg, 9.89 mmol) was added. The mixture was stirred at 25 °C for 20 h. The solution was concentrated and purified by flash column chromatography (0-70percent EtOAc/hexanes) to afford a colorless oil which was dissolved in CH2CI2 (20 mL) and treated with a 2 M solution of HCI in 1 ,4- dioxane (12.4 mL, 24.72 mmol). After stirring at 25 °C for 20 h, the solution was concentrated and azeotropically dried with toluene to afford the title compound (260.8 mg, 33percent) as a white solid. LCMS (ES) m/z 152 (M+H)+; 1 H NMR (400 MHz, DMSO-d6) δ ppm 1.59 - 1.80 (m, 2 H) 1 .90 - 2.04 (m, 2 H) 2.92 (br. s, 2 H) 3.09 (br. s, 2 H) 3.23 - 3.30 (m, 3 H) 3.40-3.41 (m, 1 H) 9.03 (d, J=3.03 Hz, 2 H).
Reference: [1] Patent: WO2011/149827, 2011, A1, . Location in patent: Page/Page column 149-150
  • 4
  • [ 188622-27-7 ]
  • [ 4045-25-4 ]
Reference: [1] Patent: EP1130016, 2001, A1,
  • 5
  • [ 109384-19-2 ]
  • [ 4045-25-4 ]
Reference: [1] Patent: US2011/92475, 2011, A1,
[2] Patent: WO2006/104406, 2006, A1,
  • 6
  • [ 79099-07-3 ]
  • [ 4045-25-4 ]
Reference: [1] Patent: US2011/92475, 2011, A1,
  • 7
  • [ 763114-26-7 ]
  • [ 4045-25-4 ]
  • [ 1174043-16-3 ]
YieldReaction ConditionsOperation in experiment
72.9% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 23℃; Example 1; 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (231 g, 1206.97 mmol) was added to 4-methoxypiperidine hydrochloride (183 g, 1206.97 mmol), 2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (300 g, 1005.80 mmol) and 4-dimethylaminopyridine (30.7 g, 251.45 mmol) in DCM (4 L) at 23° C. The resulting suspension was stirred at room temperature over night. The reaction mixture was washed with 2M HCl (5 L) and 50percent saturated sodium carbonate (3 L) before being dried over MgSO4, filtered and reduced in-vacuo to give the crude product. This was then slurried in 750 ml of ethyl acetate for 5 days, and then filtered and dried at 45° C. for 5 hours to afford 4-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)benzyl)phthalazin-1(2H)-one (compound 1)(290 g, 72.9percent).1H NMR (400.132 MHz, DMSO) δ 1.26-1.35 (1H, m), 1.40-1.49 (1H, m), 1.69-1.73 (1H, m), 1.84-1.89 (1H, m), 2.99-3.07 (1H, m), 3.25 (3H, s), 3.27-3.34 (2H, m), 3.39-3.44 (1H, m), 3.86-3.95 (1H, m), 4.33 (2H, s), 7.19-7.24 (1H, m), 7.33-7.35 (1H, m), 7.39-7.43 (1H, m), 7.81-7.91 (2H, m), 7.97 (1H, d), 8.27 (1H, d), 12.57 (1H, s); m/z (ES+) (M+H)+=396.31; HPLC tR=1.90 min.FIG. 1 shows the powder XRD pattern of the material produced, which is in Form C.FIG. 2 shows the DSC analysis of the material produced.
Reference: [1] Patent: US2011/15393, 2011, A1, . Location in patent: Page/Page column 7
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