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[ CAS No. 1214900-33-0 ] {[proInfo.proName]}

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Chemical Structure| 1214900-33-0
Chemical Structure| 1214900-33-0
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Product Details of [ 1214900-33-0 ]

CAS No. :1214900-33-0 MDL No. :MFCD28399182
Formula : C14H16BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QDKMSQYSOZVXQB-UHFFFAOYSA-N
M.W : 326.19 Pubchem ID :59276304
Synonyms :

Calculated chemistry of [ 1214900-33-0 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.43
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 79.75
TPSA : 46.61 Ų

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) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.81
Log Po/w (XLOGP3) : 3.28
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 2.51
Log Po/w (SILICOS-IT) : 2.81
Consensus Log Po/w : 2.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.96
Solubility : 0.0354 mg/ml ; 0.000109 mol/l
Class : Soluble
Log S (Ali) : -3.93
Solubility : 0.038 mg/ml ; 0.000117 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.18
Solubility : 0.0216 mg/ml ; 0.0000661 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.37

Safety of [ 1214900-33-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1214900-33-0 ]

* 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.

  • Downstream synthetic route of [ 1214900-33-0 ]

[ 1214900-33-0 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1214900-33-0 ]
  • [ 2602268-41-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 °C 2: montmorillonite / 20 °C 3: scandium tris(trifluoromethanesulfonate) / 1,2-dichloro-ethane / 60 °C
  • 2
  • [ 1214900-33-0 ]
  • [ 2602268-59-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 °C 2: montmorillonite / 20 °C
  • 3
  • [ 1214900-33-0 ]
  • [ 2624036-40-2 ]
YieldReaction ConditionsOperation in experiment
With lithium triethylborohydride In tetrahydrofuran at -78℃; for 0.5h; General procedure for synthesis of 8 and 11 General procedure: To a solution of 6 or 9 (2.0 mmol) in dry THF (8 mL) at -78 °C was added LiEt3BH (2.1 mL, 2.1 mmol, 1M in THF). After being stirred at -78 °C for 0.5 h, the reaction was quenched with saturated sodium bicarbonate aqueous solution then the mixture was extracted with EtOAc (30 mL*3). The combined organic layers were washed with brine. Dried, filtrated and concentrated to give the crude product without further purification. The residue was dissolved in MeOH (8 mL) and montmorillonite K-10 (200 mg) was added, after being stirred at rt for overnight, the mixture was filtrated through a short silica gel and concentrated to give the N,O-acetal 7 or 10. To a solution of 7 or 10 (1.0 mmol) in DCE (4 mL) was added Sc(OTf)3 (0.5 mmol), then the mixture was heated at 60 °C for 1-2 h. After being cooled to rt, the reaction was quenched with saturated sodium bicarbonate aqueous solution then the mixture was extracted with EtOAc (30 mL*3). The combined organic layers were washed with brine. Dried, filtrated and concentrated. The residue was purified by flash chromatography on silica gel to give 8 or 11.
With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; General Procedure for the Synthesis of 6 or 7 General procedure: To a solution of compound 14 or 15 (2.0 mmol) in dry THF (10 mL) was added DMAP (0.2 mmol) and Boc2O (5.0 mmol). After being stirred at room temperature for 12 h, the mixture was quenched with NH4Cl and extracted with EtOAc (30 mL × 3). The combined organic layers were washed with brine, dried over MgSO4, filtrated and concentrated. The residue was purified by flash chromatography on silica gel (PE/EA = 5:1) to give the desired product 16 or 17. The compound 16 or 17 (0.5 mmol) was dissolved in dry THF (3 mL) under Ar atmosphere. Then DIBAL-H (1 M, 1.5 equiv) was dropped slowly. After being stirred at -78 °C for 2 h, the mixture was quenched with EtOAc and potassium sodium tartrate, and extracted with EtOAc (20 mL × 3). The combined organic layers were washed with brine, dried over MgSO4, filtrated and concentrated, then obtained the crude product 6 or 7 to be used without purification because of its unstablity.
  • 4
  • [ 1214900-33-0 ]
  • [ 2624036-25-3 ]
  • [ 2624036-47-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 5
  • [ 1214900-33-0 ]
  • [ 2624036-26-4 ]
  • [ 2624036-48-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 6
  • [ 1214900-33-0 ]
  • [ 2624036-27-5 ]
  • [ 2624036-49-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 7
  • [ 1214900-33-0 ]
  • [ 2624036-28-6 ]
  • [ 2624036-50-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 8
  • [ 1214900-33-0 ]
  • [ 2624036-30-0 ]
  • [ 2624036-52-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 9
  • [ 1214900-33-0 ]
  • [ 2624036-32-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2 h / 20 °C / Inert atmosphere
  • 10
  • [ 1214900-33-0 ]
  • [ 2624036-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2: copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 2 h / 20 °C / Inert atmosphere 3: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 80 °C / Inert atmosphere
  • 11
  • [ 147497-32-3 ]
  • [ 24424-99-5 ]
  • [ 1214900-33-0 ]
YieldReaction ConditionsOperation in experiment
With dmap In tetrahydrofuran at 20℃; for 12h; General Procedure for the Synthesis of 6 or 7 General procedure: To a solution of compound 14 or 15 (2.0 mmol) in dry THF (10 mL) was added DMAP (0.2 mmol) and Boc2O (5.0 mmol). After being stirred at room temperature for 12 h, the mixture was quenched with NH4Cl and extracted with EtOAc (30 mL × 3). The combined organic layers were washed with brine, dried over MgSO4, filtrated and concentrated. The residue was purified by flash chromatography on silica gel (PE/EA = 5:1) to give the desired product 16 or 17. The compound 16 or 17 (0.5 mmol) was dissolved in dry THF (3 mL) under Ar atmosphere. Then DIBAL-H (1 M, 1.5 equiv) was dropped slowly. After being stirred at -78 °C for 2 h, the mixture was quenched with EtOAc and potassium sodium tartrate, and extracted with EtOAc (20 mL × 3). The combined organic layers were washed with brine, dried over MgSO4, filtrated and concentrated, then obtained the crude product 6 or 7 to be used without purification because of its unstablity. tert-butyl 6-bromo-1-oxo-3,4-dihydroisoquinoline-2(1H)-carboxylate (17b): White solid (581 mg, 89%); mp 81-83 °C; IR (film): vmax 2978, 1715, 1591,1310, 1231, 1146, 949, 838 cm-1; 1H NMR (400 MHz, CDCl3) δ 8.03-7.98 (m, 1H), 7.50-7.46 (m, 1H), 7.40-7.37 (m, 1H), 4.00-3.96 (m, 2H), 3.00-2.96 (m, 2H), 1.58 (s, 9H) ppm; 13C{1H} NMR (100 MHz, CDCl3) δ 163.2, 152.9, 141.3, 131.4, 130.7, 130.2, 128.4, 127.9, 83.5, 44.3, 28.1 ppm; HRMS (ESI-Orbitrap) m/z: [M + Na]+ Calcd for C14H16BrNO3Na+: 350.0185, 348.0206, found: 350.0184, 348.0208.
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