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[ CAS No. 1178884-53-1 ]

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Chemical Structure| 1178884-53-1
Chemical Structure| 1178884-53-1
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Product Details of [ 1178884-53-1 ]

CAS No. :1178884-53-1 MDL No. :MFCD21364605
Formula : C5H4BrClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :223.46 g/mol Pubchem ID :59216474
Synonyms :

Calculated chemistry of of [ 1178884-53-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.47
TPSA : 34.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 1.42
Log Po/w (WLOGP) : 1.2
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 1.81
Consensus Log Po/w : 1.57

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.61 mg/ml ; 0.00273 mol/l
Class : Soluble
Log S (Ali) : -1.76
Solubility : 3.91 mg/ml ; 0.0175 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.6
Solubility : 0.565 mg/ml ; 0.00253 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 1178884-53-1 ]

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 [ 1178884-53-1 ]

* 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 [ 1178884-53-1 ]
  • Downstream synthetic route of [ 1178884-53-1 ]

[ 1178884-53-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 74-88-4 ]
  • [ 1178884-53-1 ]
YieldReaction ConditionsOperation in experiment
79% With caesium carbonate In N,N-dimethyl-formamide for 3.33333 h; Step 3: To a solution of 4-bromo-6-chloropyridazin-3(2H)-one (1.0 equiv.) and Cs2CO3 (1.2 equiv.) in DMF (0.07 M) was added iodomethane (1.5 equiv.) drop-wise over 20 min. The resulting mixture was stirred for 3 h. The reaction mixture was then diluted with ammonium chloride, then extracted with ethyl acetate, dried over MgSO4 and concentrated in vacuo to yield as a brown solid. The oil was further purified via silica gel column chromatography eluting with 100percent heptanes to 80percent ethyl acetate:heptanes to yield 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one as an off-white solid in 79percent yield. LCMS (m/z) (M+H)=222.9/224.9, Rt=0.54 min. 1H NMR (400 MHz, ) δ ppm 3.77-3.86 (m, 3H) 7.56-7.69 (m, 1H).
68%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.166667 h; Inert atmosphere
Stage #2: at 20℃; for 1.5 h;
A 250-mL single-necked round bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 4-bromo-6-chloropyridazin-3(2H)-one (1.00 g, 4.77 mmol) and DMF (15 mL). Sodium hydride (60percent by weight in oil, 229 mg, 5.73 mmol) was added in one portion. After stirring at room temperature for 10 minutes, iodomethane (1.02 g, 7.16 mmol) was added and the reaction stirred at room temperature for 1.5 h. The reaction was then quenched with aqueous saturated sodium bicarbonate (10 mL) and the resulting solution poured into water (150 mL). The mixture was then extracted with ethyl acetate (250 mL). The organic layer was dried over sodium sulfate. The drying agent was then removed by filtration, and the filtrate was concentrated under reduced pressure to residue. Purification by column chromatography afforded 103e in a 68percent yield (722 mg) as a white solid: mp 107- 108 °C; ]H NMR (300 MHz, CDC13) δ 7.62 (s, 1H), 3.81 (s, 3H).
68%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.166667 h;
Stage #2: at 20℃; for 1.5 h;
A 250-mL single-necked round bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 4-bromo-6-chloropyridazin-3(2H)-one (1.00 g, 4.77 mmol) and DMF (15 mL). Sodium hydride (60percent by weight in oil, 229 mg, 5.73 mmol) was added in one portion. After stirring at room temperature for 10 minutes, iodomethane (1.02 g, 7.16 mmol) was added and the reaction stirred at room temperature for 1.5 h. The reaction was then quenched with aqueous saturated sodium bicarbonate (10 mL) and the resulting solution poured into water (150 mL). The mixture was then extracted with ethyl acetate (250 mL). The organic layer was dried over sodium sulfate. The drying agent was then removed by filtration, and the filtrate was concentrated under reduced pressure to residue. Purification by column chromatography afforded 103a in a 68percent yield (722 mg) as a white solid: mp 107- 108 °C; ]H NMR (300 MHz, CDC13) δ 7.62 (s, 1H), 3.81 (s, 3H).
Reference: [1] Patent: US2014/275003, 2014, A1, . Location in patent: Paragraph 0215; 0218
[2] Patent: WO2011/140488, 2011, A1, . Location in patent: Page/Page column 128
[3] Patent: WO2012/30990, 2012, A1, . Location in patent: Page/Page column 65
[4] Patent: WO2009/98144, 2009, A1, . Location in patent: Page/Page column 68-69
[5] Patent: US2010/222325, 2010, A1, . Location in patent: Page/Page column 93
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