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[ CAS No. 893566-75-1 ] {[proInfo.proName]}

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Chemical Structure| 893566-75-1
Chemical Structure| 893566-75-1
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Product Details of [ 893566-75-1 ]

CAS No. :893566-75-1 MDL No. :MFCD08752230
Formula : C14H18BrNO2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :GKXSAKJDUDGJFB-UHFFFAOYSA-N
M.W : 312.20 Pubchem ID :59463272
Synonyms :

Calculated chemistry of [ 893566-75-1 ]      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 : 79.32
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) : 3.36
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 : 3.24

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 : 2.46

Safety of [ 893566-75-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 893566-75-1 ]

* 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.

  • Downstream synthetic route of [ 893566-75-1 ]

[ 893566-75-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 226942-29-6 ]
  • [ 24424-99-5 ]
  • [ 75416-51-2 ]
  • [ 893566-75-1 ]
  • [ 893566-74-0 ]
YieldReaction ConditionsOperation 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).
  • 2
  • [ 893566-75-1 ]
  • [ 893566-74-0 ]
  • [ 73183-34-3 ]
  • [ 893566-72-8 ]
  • [ 893566-73-9 ]
YieldReaction ConditionsOperation 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).
  • 3
  • [ 893566-75-1 ]
  • [ 1423161-93-6 ]
  • [ 1423161-80-1 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 85℃; for 2h;Inert atmosphere; Sealed tube; A vial was charged with N-(2,4-dimethoxybenzyl)-l-methyl-3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-N-(l,2,4-thiadiazol-5-yl)-lH-indole-6-sulfonamide (Intermediate H)(0.188 g, 0.330 mmol), tert-butyl 8-bromo-3,4-dihydroisoquinoline- 2(lH)-carboxylate (0.257 g, 0.824 mmol), potassium phosphate (0.315 g, 1.483 mmol), and PdCl2(dppf)-CH2Cl2 adduct (0.027 g, 0.033 mmol). DMF (2.197 ml) was added, and the vial was flushed with argon, sealed, and stirred at 85 °C for two hours. Additional tert-butyl 8-bromo-3,4-dihydroisoquinoline-2(lH)-carboxylate (Oakwood Inc., West Columbia, South Carolina ) (0.257 g, 0.824 mmol) was added and the reaction was stirred at 85 °C for two hours. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 40g silica gel column (Teledyne Isco, Lincoln, NE) , gradient elution 0 to 100percent EtOAc:Hex) to afford tert- butyl 8-(6-( -(2,4-dimethoxybenzyl)-N-(l,2,4-thiadiazol-5-yl)sulfamoyl)-l-methyl-lH- indol-3-yl)-3,4-dihydroisoquinoline-2(lH)-carboxylate as a light yellow solid.
  • 4
  • [ 24424-99-5 ]
  • 8-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride [ No CAS ]
  • [ 893566-75-1 ]
YieldReaction ConditionsOperation in experiment
95.5% With triethylamine; In tetrahydrofuran; at 25℃; for 1h; To a solution of 8-bromo-l,2,3,4-tetrahydroisoquinoline HCl salt (3.50 g, 14.1 mmol, 1 eq) in tetrahydrofuran (50 mL) was added triethylamine (2.85 g, 28.2 mmol, 3.9 mL, 2 eq.) and B0C2O (3.10 g, 14.2 mmol, 1.01 eq.). The mixture was stirred at 25 °C for 1 hour. The reaction mixture was diluted with H20 (50 mL) and extracted with ethyl acetate (100 mL*3). The organic phases were washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give Example 121A (4.20 g, yield = 95.5percent). [0215] NMR (400MHz, CDCb) delta 7.41 (d, J=7.6 Hz, 1H), 7.12 - 7.01 (m, 2H), 4.54 (s., 2H), 3.64 (t, J=5.2 Hz, 2H), 2.84 (t, J=5.2 Hz, 2H), 1.51 (s, 9H).
94% With triethylamine; In dichloromethane; at 20℃; for 1.5h; To the solution of 8-bromo-1,2,3,4-tetrahydroiso- quinoline HC1 (1 g, 4.72 mmol) in DCM (20 mE) was added 13oc20 (1030mg, 4.72 mmol) andNEt3 (960mg, 9.43 mmol). The mixture was stirred at 20° C. for 1 .5 h. The mixture was concentrated in vacuo to afford crude product (2000 mg). The crude was purified by silica gel chromatography eluted withEtOAc in petroleum ether from 0 to 30percent to afford the desiredproduct (1.36 mg, 94percent). ?H NMR (400 MHz, CDC13) oe ppm7.42 (d, J=7.5 Hz, 1H), 7.14-6.97 (m, 2H), 4.61-4.48 (m, 2H),3.64 (t, J=5.4 Hz, 2H), 2.90-2.75 (m, 2H), 1.50 (s, 9H)
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