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Chemistry
Organic Building Blocks
Aryls
nitrobenzene
3-Bromo-N-methoxy-N-methyl-5-nitrobenzamide
Chemistry
Organic Building Blocks
Aryls
Amines Bromides Amides Nitroes Benzene Compounds
nitrobenzene
N-methoxy-N-methylbenzamide 1-bromo-3-nitrobenzene benzoyl

[ CAS No. 1519917-98-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1519917-98-6
Chemical Structure| 1519917-98-6
Structure of 1519917-98-6 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 1519917-98-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 1519917-98-6 ]

Product Details of [ 1519917-98-6 ]

CAS No. :1519917-98-6 MDL No. :MFCD25132888
Formula : C9H9BrN2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :GRINWUSYNUMATI-UHFFFAOYSA-N
M.W : 289.08 Pubchem ID :81530379
Synonyms :

Calculated chemistry of [ 1519917-98-6 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.95
TPSA : 75.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 1.47
Log Po/w (SILICOS-IT) : -0.59
Consensus Log Po/w : 1.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.386 mg/ml ; 0.00134 mol/l
Class : Soluble
Log S (Ali) : -3.16
Solubility : 0.201 mg/ml ; 0.000696 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.42
Solubility : 1.09 mg/ml ; 0.00377 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.33

Safety of [ 1519917-98-6 ]

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 [ 1519917-98-6 ]

* 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 [ 1519917-98-6 ]

[ 1519917-98-6 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 6307-83-1 ]
  • [ 6638-79-5 ]
  • 3-bromo-N-methoxy-N-methyl-5-nitrobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% To a solution of 3-brorno-5-nitrobenzoic acid (95a) (5 g, 20.32 mmol) in toluene (40mL) was added thionyl chloride(14.83 rnL, 203 mmol) and heated at reflux for I Ii. Thereaction mixture was concentrated in vacuum to dryness. The residue obtained wasdissolved in CH2CI2 (40.0 mL) and added N,O-dimethylhydroxylarnine hydrochloride (2.97g. 30.5 mmol) followed by triethylamine (14.16 mL, 102 mmol). The reaction mixture was stirred at room temperature overnight, washed with I N HCI (40 mL), I N NaOH (40 mL), water (40 mL), brine (40 mL), dried filtered and concentrated in vacuum. The residue obtained was purified by flash column chromatography (silica gel 40 g. eluting with 0-100% ethyl acetate in hexane) to furnish 3-bromo-N-methoxy-N-methyl-5-nitrobenzamide(95b) (4.5 g, 15.57 mmol, 77% yield) as a yellow oil; ?H NMR (300 MHz, DMSO-d6) 68.51 (t,J2.OHz, IH), 8.37 (dd,J=2.1, 1.4Hz, IH), 8.23 (dd,J 1.8, 1.4 Hz, IFI), 3.57(s, 3H), 3.31 (s, 3H).
Reference： [1]Patent: WO2015/134998,2015,A1 .Location in patent: Page/Page column 393; 394
  • 2
  • [ 1519917-98-6 ]
  • [ 1809016-66-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium (II) acetate; tricyclohexylphosphine / water; toluene / 50 h / 120 °C / Inert atmosphere 2: methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate / 0.75 h / 0 °C
Reference： [1]Current Patent Assignee: BIOCRYST PHARMACEUTICALS INC - WO2015/134998, 2015, A1
  • 3
  • [ 1519917-98-6 ]
  • [ 1809016-67-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium (II) acetate; tricyclohexylphosphine / water; toluene / 50 h / 120 °C / Inert atmosphere 2: methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate / 0.75 h / 0 °C 3: tetrahydrofuran / 3 h / 0 - 20 °C
Reference： [1]Current Patent Assignee: BIOCRYST PHARMACEUTICALS INC - WO2015/134998, 2015, A1
  • 4
  • [ 1519917-98-6 ]
  • [ 1809016-68-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium (II) acetate; tricyclohexylphosphine / water; toluene / 50 h / 120 °C / Inert atmosphere 2: methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate / 0.75 h / 0 °C 3: tetrahydrofuran / 3 h / 0 - 20 °C 4: methanol; sodium tetrahydroborate / 0.25 h / 0 °C
Reference： [1]Current Patent Assignee: BIOCRYST PHARMACEUTICALS INC - WO2015/134998, 2015, A1
  • 5
  • [ 1519917-98-6 ]
  • [ 1809016-69-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: palladium (II) acetate; tricyclohexylphosphine / water; toluene / 50 h / 120 °C / Inert atmosphere 2: methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate / 0.75 h / 0 °C 3: tetrahydrofuran / 3 h / 0 - 20 °C 4: methanol; sodium tetrahydroborate / 0.25 h / 0 °C 5: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 37 h / 20 °C / Inert atmosphere
Reference： [1]Current Patent Assignee: BIOCRYST PHARMACEUTICALS INC - WO2015/134998, 2015, A1
  • 6
  • [ 1519917-98-6 ]
  • [ 1809016-70-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: palladium (II) acetate; tricyclohexylphosphine / water; toluene / 50 h / 120 °C / Inert atmosphere 2.1: methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate / 0.75 h / 0 °C 3.1: tetrahydrofuran / 3 h / 0 - 20 °C 4.1: methanol; sodium tetrahydroborate / 0.25 h / 0 °C 5.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 37 h / 20 °C / Inert atmosphere 6.1: thionyl chloride / dichloromethane / 3 h / 0 - 20 °C 6.2: 2 h / Reflux
Reference： [1]Current Patent Assignee: BIOCRYST PHARMACEUTICALS INC - WO2015/134998, 2015, A1
  • 7
  • [ 1519917-98-6 ]
  • [ 1809010-97-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: palladium (II) acetate; tricyclohexylphosphine / water; toluene / 50 h / 120 °C / Inert atmosphere 2.1: methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate / 0.75 h / 0 °C 3.1: tetrahydrofuran / 3 h / 0 - 20 °C 4.1: methanol; sodium tetrahydroborate / 0.25 h / 0 °C 5.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 37 h / 20 °C / Inert atmosphere 6.1: thionyl chloride / dichloromethane / 3 h / 0 - 20 °C 6.2: 2 h / Reflux 7.1: methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate / 0.5 h / 0 °C
Reference： [1]Current Patent Assignee: BIOCRYST PHARMACEUTICALS INC - WO2015/134998, 2015, A1
  • 8
  • [ 1519917-98-6 ]
  • [ 411235-57-9 ]
  • [ 1809016-65-6 ]
YieldReaction ConditionsOperation in experiment
73% With palladium (II) acetate; tricyclohexylphosphine In water; toluene at 120℃; for 50h; Inert atmosphere; 2 Step-2: Preparation of 3-cyclopropyl-N-methoxy-N-methyl-5-nitrobenzamide (95c) To a 250 mL single-neck flask with a magnetic stir bar was charged with 3-brorno-N-rnethoxy-N-methyl-5-nitrobenzamide (95b) (2.394 g, 8.28 mrnol), cyclopropylboronic acid (1.423 g, 16.56 inmol), potassium phosphate monohydrate (4.77 g, 20.70 mrnol), tricyclohexylphosphine (0.697 g, 2.484 mmol) and palladium(I I) acetate trimer (0.837 g, 1 .242 mrnol). The flask was degassed and purged with nitrogen, this cycle was repeatedtwice, and then the reaction mixture was diluted with toluene (30 mL) and water (10 mL). The reaction mixture was again degassed and purged with nitrogen twice, and then the reaction mixture was purged with nitrogen for 5 mm and started heating to reflux at 120 °C and stirred for 50 h, TLC analysis (ethyl acetate/hexanes, 3/7, v/v) shows reaction was complete. The reaction mixture was cooled to room temperature, quenched with water (50mL) and extracted with ethyl acetate (3 x 75 rnL). The organic layers were combined washed with brine (50 inL), dried over anhydrous MgSO4 (10 g), filtered and excess solvent was removed under reduced pressure. The residue and was purified by flash column chromatography (40 g silica gel, eluting with ethyl acetate in hexanes from 0-50%) to furnish 3-cyclopropyl-N-methoxy-N-methyl-5-nitrobenzamide (95c) (1.523 g, 73 % yield)as a pale yellow oil; ‘H NMR (300 MHz, DMSO-d(.) 6 8.12 (dd, .1= 2.2, 1.4 Hz, I H), 8.03(t,.1 2.0 Hz, IN), 7.71 (t,J= 1.6 Hz, IH), 3.56 (s, 3H), 3.29 (s, 3H), 2.20 (tt,.1= 8.3, 5.0Hz, IH), 1.14- 1.03 (m, 2K), 0.85 (dt, .1=6.9,4.6 Hz, 2H); MS (ES4): MS (ES±) 251.1(M±l), 273.1 (M+Na).
73% With palladium diacetate; potassium carbonate; tricyclohexylphosphine In water; toluene at 110℃; for 50h;
Reference： [1]Current Patent Assignee: BIOCRYST PHARMACEUTICALS INC - WO2015/134998, 2015, A1 Location in patent: Page/Page column 393; 394
[2]Delaney, Connor P.; Kassel, Vincent M.; Denmark, Scott E. [ACS Catalysis, 2020, vol. 10, # 1, p. 73 - 80]
  • 9
  • [ 1519917-98-6 ]
  • [ 2696246-02-1 ]
  • [ 1809016-65-6 ]
YieldReaction ConditionsOperation in experiment
72% With potassium trimethylsilonate; palladium diacetate; tricyclohexylphosphine In 1,4-dioxane at 100℃; for 3h;
Reference： [1]Delaney, Connor P.; Kassel, Vincent M.; Denmark, Scott E. [ACS Catalysis, 2020, vol. 10, # 1, p. 73 - 80]

Tags: 1519917-98-6 synthesis path| 1519917-98-6 SDS| 1519917-98-6 COA| 1519917-98-6 purity| 1519917-98-6 application| 1519917-98-6 NMR| 1519917-98-6 COA| 1519917-98-6 structure

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