[ CAS No. 893566-74-0 ] {[proInfo.proName]}

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2D 3D

Structure of 893566-74-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 893566-74-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 893566-74-0 ]

SDS Specification

Alternatived Products of [ 893566-74-0 ]

Product Details of [ 893566-74-0 ]

CAS No. :	893566-74-0	MDL No. :	MFCD08752228
Formula :	C₁₄H₁₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SZIPGDGOBMFCEH-UHFFFAOYSA-N
M.W :	312.20	Pubchem ID :	49761184
Synonyms :

Calculated chemistry of [ 893566-74-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	79.33
TPSA :	29.54 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.43
Log Po/w (XLOGP3) :	3.33
Log Po/w (WLOGP) :	3.21
Log Po/w (MLOGP) :	3.18
Log Po/w (SILICOS-IT) :	3.11
Consensus Log Po/w :	3.25

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.92
Solubility :	0.0373 mg/ml ; 0.00012 mol/l
Class :	Soluble
Log S (Ali) :	-3.63
Solubility :	0.0737 mg/ml ; 0.000236 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.3
Solubility :	0.0157 mg/ml ; 0.0000504 mol/l
Class :	Moderately soluble

Medicinal Chemistry

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

Safety of [ 893566-74-0 ]

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 [ 893566-74-0 ]

* 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 [ 893566-74-0 ]
Downstream synthetic route of [ 893566-74-0 ]

[ 893566-74-0 ] Synthesis Path-Upstream 1~1

1
[ 893566-74-0 ]
[ 622867-52-1 ]

Reference： [1] Patent: WO2017/205193, 2017, A1,

[ 893566-74-0 ] Synthesis Path-Downstream 1~2

1
[ 226942-29-6 ]
[ 24424-99-5 ]
[ 75416-51-2 ]
[ 893566-75-1 ]
[ 893566-74-0 ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of 6-bromo-1,2,3,4-tetrahydroisoquinoline and 8-bromo-1,2,3,4-tetrahydroisoquinoline (22.1 mmol) in THF (100 mL) was added DIPEA (22.1 mmol) and BOC2O (24 mmol). The reaction mixture was allowed to stir at rt over the weekend and then concentrated. Water (5 mL) was added to the residue and the pH was adjusted to 2 by the addition of 1N H3PO4. The mixture was extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate and tert-butyl 8-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (6.04 g, 88%) as a yellow oil.
		Dry THF (50 mL) and DIPEA (1.3 mL, 7.5 mmol) were added followed by BOC- anhydride (1.8 g, 8.2 mmol). The mixture was stirred overnight at RT. The volatiles were evaporated and the residue was taken up in water. The pH was adjusted to 2 with IM phosphoric acid and the product was extracted twice with EtOAc. The combined organic phases were washed with brine made slightly alkaline with saturated sodium bicarbonate, dried, filtered and concentrated. The crude product was purified by column chromatography with EtOAc-heptanes (1:50 through 1:20) to give 2.24 g (96%) of a 3:1 mixture of the title product and fert-butyl 8-bromo-3,4-dihydroisoquinoline-2(lH)- carboxylate. EPO <DP n="26"/>LC-MS m/z 256/258 (M-56);1H NMR (CDCl3) delta 7.31 (dd, IH), 7.30 (br s, IH), 6.98 (d, IH), 4.52 (s, 2H), 3.63 (t, 2H), 2.81 (t, 2H) and 1.50 (s, 9H) ppm (6-isomer).1H NMR (CDCl3) delta 7.42 (dd, IH), 7.12-7.01 (m's, 2H), 4.55 (s, 2H), 3.64 (t, 2H), 2.84 (t, 2H) and 1.51 (s, 9H) ppm (8-isomerV
		Dry THF (50 mL) and DIPEA (1.3 mL, 7.5 mmol) were added followed by BOC- anhydride (1.8 g, 8.2 mmol). The mixture was stirred at RT overnight. The volatiles were i5 evaporated and the residue was taken up in water. The pH was adjusted to 2 with IM phosphoric acid and the product was extracted twice with EtOAc. The combined organic phases were washed with brine made slightly alkaline with saturated sodium bicarbonate, dried, filtered and concentrated. The crude product was purified by column chromatography with EtOAc-heptanes (1:50 through 1:20) to give 2.24 g (96%) of a 3:120 mixture of the title product and tert-butyl 8-bromo-3,4-dihydroisoquinoline-2(lH)- carboxylate. LC-MS mlz 256, 258 (M-56);1H NMR (CDCl3) delta 7.31 (dd, IH), 7.30 (br s, IH), 6.98 (d, IH), 4.52 (s, 2H), 3.63 (t, 2H),2.81 (t, 2H) and 1.50 (s, 9H) ppm (6-isomer).25 11HH N NMMRR ( (CCDDCCll33)) delta delta 77..4422 ( (dddd,, I IHH)),, 77..112-7.01 (m, 2H), 4.55 (s, 2H), 3.64 (t, 2H), 2.84 (t, 2H) and 1.51 (s, 9H) ppm (8-isomer).

Reference： [1]Patent: US2008/171754,2008,A1 .Location in patent: Page/Page column 101; 102
[2]Patent: WO2006/65215,2006,A1 .Location in patent: Page/Page column 17; 24-25
[3]Patent: WO2006/65216,2006,A1 .Location in patent: Page/Page column 16; 24

2
[ 893566-75-1 ]
[ 893566-74-0 ]
[ 73183-34-3 ]
[ 893566-72-8 ]
[ 893566-73-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 85℃; for 4h;	A solution of tert-butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate and <strong>[893566-75-1]tert-butyl 8-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate</strong> (19.5 mmol), bis(pinacolato)diboron (21.4 mmol) and potassium acetate (61 mmol) in DMF (100 mL) was degassed. To this solution was added PdCl2dppf (1:1 complex with DCM, 0.8 mmol). The reaction mixture was heated at 85 C. for 4 hr and then allowed to cool to room temperature and diluted with EtOAc. The solution was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate and tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate. LCMS: (FA) ES+360 (for each).
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 81℃;	tert-Butyl 6-( 4,4,5 ,5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-vD-3 ,4-dihvdroisoquinoline- 2(liD-carboxylate is A 3:1 mixture (0.49 g, 1.6 mmol) of fert-butyl 6-bromo-3,4-dihydroisoquinoline-2(lH)- carboxylate and tert-butyl 8~bromo-3,4-dihydroisoquinoline-2(li/)- carboxylate, bis(pinacolato)diborane (0.45 g, 1.8 mmol), PdCl2 x dppf (0.039 g, 0.048 mmol), potassium acetate (0.48 g, 4.8 mmol) and DMF (8.0 mL) was heated at 81 C ' WeligKtyThe~slve1alphat^30 twice with EtOAc. The organic phase was dried, filtered and concentrated. Column chromatography with EtO Ac-heptanes (1:10 through 1:4) gave 0.24 g of a 4:1 mixture of EPO <DP n="25"/>the title product and ter/-butyl 8-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4- dihydroisoquinoline-2(lH)-carboxylate.1H NMR (CDCl3) delta 7.62 (d, IH), 7.60 (s, IH), 7.13 (d, IH), 4.59 (s, 2H), 3.64 (t, 2H), 2. .85 (t, 2H), 1.50 (s, 9H) and 1.35 (s, 12H) ppm (6-isomer). 1H NMR (CDCl3) delta 7.69 (d, IH), 7.24-7.14 (m's, 2H), 4.88 (s, 2H), 3.64 (t, 2H), 2.85 (t, 2H), 1.50 (s, 9H) and 1.35 (s, 12H) ppm (8-isomef).
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 81℃;	A 3:1 mixture (0.49 g, 1.6 mmol) of tert-mty 6-bromo-3,4-dihydroisoquinoline-2(lH)- carboxylate and fert-butyl 8-bromo-3,4-dihydroisoquinoline-2(lH)- carboxylate, bis(pinacolato)diborane (0.45 g, 1.8 mmol), PdCl2 x dppf (0.039 g, 0.048 mmol), potassium acetate (0.48 g, 4.8 mmol) and DMF (8.0 mL) was heated at 81 0C overnight. The solvent was evaporated, the residue taken up in water-brine and washed twice with EtOAc. The organic phase was dried, filtered and concentrated. Column chromatography with EtOAc-heptanes (1:10 through 1:4) gave 0.24 g of a 4:1 mixture of the title product and tert-butyl 8-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4- dihydroisoquinoline-2( lH)-carboxylate.1H NMR (CDCl3) delta 7.62 (d, IH), 7.60 (s, IH), 7.13 (d, IH), 4.59 (s, 2H), 3.64 (t, 2H)5 2.85 (t, 2H), 1.50 (s, 9H) and 1.35 (s, 12H) ppm (6-isomer). 1H NMR (CDCl3) delta 7.69 (d, IH), 7.24-7.14 (m, 2H)5 4.88 (s, 2H), 3.64 (t, 2H), 2.85 (t, 2H), 1.50 (s, 9H) and 1.35 (s, 12H) ppm (8-isomer).

Reference： [1]Patent: US2008/171754,2008,A1 .Location in patent: Page/Page column 102
[2]Patent: WO2006/65215,2006,A1 .Location in patent: Page/Page column 23-24
[3]Patent: WO2006/65216,2006,A1 .Location in patent: Page/Page column 23

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Isomers

Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Ester Cleavage ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

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[ 893566-74-0 ]

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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 893566-74-0 ] {[proInfo.proName]}

Quality Control of [ 893566-74-0 ]

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Product Details of [ 893566-74-0 ]

Calculated chemistry of [ 893566-74-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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[ 893566-74-0 ] Synthesis Path-Upstream 1~1

[ 893566-74-0 ] Synthesis Path-Downstream 1~2

Technical Information

Related Functional Groups of [ 893566-74-0 ]

Bromides

Amides

Related Parent Nucleus of [ 893566-74-0 ]

Tetrahydroisoquinolines

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[ 893566-74-0 ]

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[ 893566-74-0 ]