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[ CAS No. 24036-47-3 ] {[proInfo.proName]}

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Chemical Structure| 24036-47-3
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Product Details of [ 24036-47-3 ]

CAS No. :24036-47-3 MDL No. :MFCD08669851
Formula : C9H8BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PXVXLTXGIDUXBH-UHFFFAOYSA-N
M.W : 242.07 Pubchem ID :53217383
Synonyms :

Calculated chemistry of [ 24036-47-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.86
TPSA : 29.54 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) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 1.75
Log Po/w (WLOGP) : 1.42
Log Po/w (MLOGP) : 1.56
Log Po/w (SILICOS-IT) : 2.04
Consensus Log Po/w : 1.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.78
Solubility : 0.397 mg/ml ; 0.00164 mol/l
Class : Soluble
Log S (Ali) : -1.99
Solubility : 2.49 mg/ml ; 0.0103 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.16
Solubility : 0.167 mg/ml ; 0.000692 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.26

Safety of [ 24036-47-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24036-47-3 ]

* 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.

  • Downstream synthetic route of [ 24036-47-3 ]

[ 24036-47-3 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 21744-84-3 ]
  • [ 24036-47-3 ]
  • 2
  • [ 24036-52-0 ]
  • [ 74-88-4 ]
  • [ 24036-47-3 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In acetone
Stage #1: 6-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere of nitrogen; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; 10.i To sodium hydride (63 mg) in DMF (3 rnL) under an atmosphere of nitrogen was added 6- bromo-2H-benzo[b][l,4]oxazin-3(4H)-one (0.3 g) and the mixture was stirred at room temperature for Ih. Methyl iodide (0.123 mL) was added and the mixture was stirred overnight at room temperature. The mixture was poured onto ice / water and extracted into ethyl acetate (x2). The ethyl acetate was washed with water (x3), dried and the solvent was evaporated. The resulting material was purified by chromatography on silica eluting with 10% ethyl acetate / ohexane to afford the sub-titled compound (299 mg).1H NMR (399.826 MHz, d6-DMSO) δ 7.33 (d, IH), 7.18 (dd, IH), 6.96 (d, IH), 4.67 (s, 2H), 3.26 (s, 3H).
Stage #1: 6-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one With sodium hydride In water; N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: methyl iodide In water; N,N-dimethyl-formamide at 20℃; for 1h; 31.1 6-bromo-4-methyl-2H-1,4-benzoxazin-3(4H)-one Sodium hydride (0.10 g, 2.6 mmol) was added to a solution of 6-bromo-2H-1,4-benzoxazin-3(4H)-one (0.49 g, 2.1 mmol) in N,N-dimethylformamide (3 mL) under nitrogen. After the mixture was stirred at r.t. for 10 min, methyl iodide (0.27 mL, 4.3 mmol) was added. The reaction mixture was stirred at r.t. for 1 h. Then 10 mL of water was added to the mixture, and a white precipitate was removed by filtration, washed with water, and dried under vacuum to afford the product which was directly used in next step reaction without further purification. LCMS (M+H)+=242.2/244.2.
  • 3
  • [ 24036-47-3 ]
  • [ 24036-46-2 ]
YieldReaction ConditionsOperation in experiment
With bromine In acetic acid
  • 4
  • [ 5466-88-6 ]
  • [ 24036-47-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Br2 / acetic acid 2: KOH / acetone
  • 5
  • [ 24036-48-4 ]
  • [ 24036-47-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. KOH 2: KOH / acetone
  • 6
  • [ 24036-47-3 ]
  • [ 24049-83-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Br2 / acetic acid 2: P2S5 / xylene
  • 7
  • [ 24036-47-3 ]
  • [ 73183-34-3 ]
  • [ 1218790-29-4 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate In water; acetonitrile at 85℃; for 18h; Inert atmosphere of nitrogen; 10.ii To 6-bromo-4-methyl-2H-benzo[b][l,4]oxazin-3(4H)-one (Example 10, step (i), 0.14 g) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (0.220 g) in acetonitrile (6 niL) was added potassium acetate (0.170 g) and nitrogen was bubbled through the mixture. 1,1 bis(Di- te/t-butylphosphino)ferrocene palladium dichloride (5 mg) was added and the mixture was heated at 85 0C for 18h. The mixture was absorbed onto silica and purified by chromatography on silica using 5-100% ethyl acetate / ohexane as eluent to afford the subtitled compound (154 mg).m/e (APCI+) 290 [M+Η]+
  • 8
  • [ 24036-47-3 ]
  • 7-bromo-6-cyclopropyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium phosphate; palladium diacetate; ruphos / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere; Sealed tube 2: bromine; acetic acid / 12 h / 20 °C
  • 9
  • [ 24036-47-3 ]
  • 6-cyclopropyl-4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium phosphate; palladium diacetate; ruphos / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere; Sealed tube 2: bromine; acetic acid / 12 h / 20 °C 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 16 h / 100 °C / Sealed tube
  • 10
  • [ 24036-47-3 ]
  • [ 411235-57-9 ]
  • 6-cyclopropyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With potassium phosphate; palladium diacetate; ruphos In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; Sealed tube; 1 6-Cyclopropyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one To a nitrogen purged solution of 6-bromo-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one (1.50 g, 6.20 mmol, prepared by following the procedure as described in WO2010128324) in 1,4-dioxane (5 mL) was added RuPhos (75 mg, 0.16 mmol), cyclopropylboronic acid (0.64 g, 7.44 mmol), potassium phosphate (3.29 g, 15.5 mmol) and Pd(OAc)2 (139 mg, 0.62 mmol) sequentially. The resulting mixture was heated in sealed tube at 100° C. for 12 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and filtered through celite. The filtrate was concentrated under reduced pressure and the crude product was purified by flash column chromatography (silica gel, 20% ethyl acetate-hexane system as eluent) to afford 200 mg (16%) of the title compound as white solid. 1HNMR (400 MHz, CDCl3) δ 6.89 (d, J=8.0 Hz, 1H), 6.77-6.65 (m, 2H), 4.59 (s, 2H), 3.37 (s, 3H), 1.94-1.87 (m, 1H), 0.99-0.94 (m, 2H), 0.68-0.64 (m, 2H); GC-MS (m/z) 203 (M)+.
  • 11
  • [ 110-91-8 ]
  • [ 24036-47-3 ]
  • 4-methyl-6-morpholino-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate; C42H41ClN5PPd In tetrahydrofuran; tert-Amyl alcohol at 80℃; for 16h; Inert atmosphere; 6.2. General procedure for Buchwald-Hartwig aminations General procedure: An oven dried 4 mL vial was fitted with a magnetic stir bar, then charged with the (hetero)aryl halide (0.5 mmol), the amine (0.6 mmol), 7 (4 mg, 0.01 equiv.), and degassed 2-methylbutan-2-ol (0.5 mL). The reaction mixture was placed under nitrogen, after which KOtBu (1.0Min THF, 0.75 mL,1.5 eq.)was added. The vialwas placed into a pre-heated 80 °C reaction block for 16 h. After cooling, the mixture was diluted with 2 mL of half-saturated NH4Cl solution and 10-20 mL of EtOAc. The EtOAc extract was dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography using an appropriate hexane e EtOAc solvent gradient.
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