[ CAS No. 283173-80-8 ] {[proInfo.proName]}

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2D 3D

Structure of 283173-80-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 283173-80-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 283173-80-8 ]

SDS Specification

Alternatived Products of [ 283173-80-8 ]

Product Details of [ 283173-80-8 ]

CAS No. :	283173-80-8	MDL No. :	MFCD23703297
Formula :	C₁₁H₈BrFN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DIUAWEVAOAYVBP-UHFFFAOYSA-N
M.W :	283.10	Pubchem ID :	22266717
Synonyms :

Calculated chemistry of [ 283173-80-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.18
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	65.72
TPSA :	44.89 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	2.49
Log Po/w (WLOGP) :	2.39
Log Po/w (MLOGP) :	2.36
Log Po/w (SILICOS-IT) :	3.71
Consensus Log Po/w :	2.53

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.58
Solubility :	0.0744 mg/ml ; 0.000263 mol/l
Class :	Soluble
Log S (Ali) :	-3.08
Solubility :	0.237 mg/ml ; 0.000836 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.18
Solubility :	0.00187 mg/ml ; 0.00000659 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.23

Safety of [ 283173-80-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302-H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 283173-80-8 ]

* 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 [ 283173-80-8 ]
Downstream synthetic route of [ 283173-80-8 ]

[ 283173-80-8 ] Synthesis Path-Upstream 1~2

1
[ 283173-80-8 ]
[ 518336-26-0 ]
[ 283173-50-2 ]

Yield	Reaction Conditions	Operation in experiment
6.82 g	With bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; sodium carbonate In methanol; water at 60℃; for 4 h; Inert atmosphere	2-Bromo-8-fluoro-4,5-dihydro-lH-azepino[5,4,3-cd]indol-6(3H)-one (10 g; 35.3 mmol), prepared according to process described in Example 3, sodium carbonate (3.74 g; 35.3 mmol), bis(triphenylphosphine)palladium(II) diacetate (0.529 g; 0.71 mmol) and (4-((methylamino)methyl)phenyl)boronic acid solution (75 ml; 45.9 mmol), prepared according to process described in Example 2, are charged into a three-necked round bottom flask, followed by inertisation with nitrogen. A previously degassed mixture of methanol (130 mL) and water (40 mL) is added and the reaction mixture is stirred at 60°C for 4 hours. The reaction mixture is cooled to ambient temperature followed by addition of activated carbon. The mixture is stirred at ambient temperature for one hour, heated to 50 °C, stirred for another hour and then filtered through a layer of celite. The solution of 8-fluoro-2-(4- ((methylamino)methyl)phenyl)-4,5-dihydro-lH-azepino[5,4,3-cd]indol-6(3H)-one is concentrated to about 110 mL, heated to 40°C followed by dropwise addition of water (40 mL). Reaction mixture is cooled to ambient temperature and stirred for 17 hours at ambient temperature and additional one hour at 0-5°C. Solid is filtered off, washed with water and dried in vacuum oven at 50°C for 5 hours. Crude material (9.5 g) is suspended in methanol (95mL) at reflux temperature and stirred for 20 minutes. Suspension is than cooled down and stirred for 17 hours at ambient temperature and 1.5 hour at 0-5°C. Crystals are filtered off, washed with methanol and dried in vacuum oven at 50°C for 4 hours to obtain 6.82 g of Rucaparib base.

Reference： [1] Patent: WO2018/140377, 2018, A1, . Location in patent: Paragraph 00325; 00327

2
[ 283173-80-8 ]
[ 283173-50-2 ]

Reference： [1] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
[2] Organic Process Research and Development, 2012, vol. 16, # 12, p. 1897 - 1904
[3] ACS Chemical Neuroscience, 2018, vol. 9, # 6, p. 1259 - 1263

[ 283173-80-8 ] Synthesis Path-Downstream 1~1

1
[ 912369-50-7 ]
[ 283173-80-8 ]
8-fluoro-5-(4-(piperazin-1-yl)phenyl)-2,3,4,6-tetrahydro-1H-azepino[5,4,3-cd]indol-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; at 90℃; for 2h;	General procedure: The boric acid or borate ester intermediates (B, D, F and H)(1.1 mmol, 1.1 eq), compound A (1 mmol, 1 eq), Na2CO3 (2 mmol, 2eq) and 10 mL dioxane were placed into a 50 mL three-neckedbottle, the reaction system was evacuated and backfilled withargon three times. Then Pd(dppf)Cl2 (0.05 mmol, 0.05 eq) wasadded to the reaction bottle under argon flow. The resulting solutionwasheated to 90 C and stirred at this temperature for 2 h. The reactionwas monitored by TLC. The mixturewas diluted withwaterand extracted with ethyl acetate. The combined organic layers werewashed with brine, dried over anhydrous Na2SO4, and concentratedto give a crude product, which was purified by column chromatographyto give the target compounds.

Reference： [1]European Journal of Medicinal Chemistry,2022,vol. 227

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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[ 283173-80-8 ]

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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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[ CAS No. 283173-80-8 ] {[proInfo.proName]}

Quality Control of [ 283173-80-8 ]

Related Doc. of [ 283173-80-8 ]

Product Details of [ 283173-80-8 ]

Calculated chemistry of [ 283173-80-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 283173-80-8 ]

Application In Synthesis of [ 283173-80-8 ]

[ 283173-80-8 ] Synthesis Path-Upstream 1~2

[ 283173-80-8 ] Synthesis Path-Downstream 1~1

Technical Information

Related Functional Groups of [ 283173-80-8 ]

Fluorinated Building Blocks

Bromides

Amides

Related Parent Nucleus of [ 283173-80-8 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 283173-80-8 ]

Related Parent Nucleus of
[ 283173-80-8 ]