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[ CAS No. 1246552-90-8 ] {[proInfo.proName]}

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Product Details of [ 1246552-90-8 ]

CAS No. :1246552-90-8 MDL No. :MFCD18250414
Formula : C9H5BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :ZLAFRLYZTMTUOQ-UHFFFAOYSA-N
M.W : 242.50 Pubchem ID :57415769
Synonyms :

Calculated chemistry of [ 1246552-90-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.45
TPSA : 12.89 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) : -5.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 3.75
Log Po/w (WLOGP) : 3.65
Log Po/w (MLOGP) : 2.85
Log Po/w (SILICOS-IT) : 3.76
Consensus Log Po/w : 3.27

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.32
Solubility : 0.0115 mg/ml ; 0.0000476 mol/l
Class : Moderately soluble
Log S (Ali) : -3.71
Solubility : 0.0469 mg/ml ; 0.000194 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.17
Solubility : 0.00162 mg/ml ; 0.00000668 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.64

Safety of [ 1246552-90-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1246552-90-8 ]

* 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.

  • Downstream synthetic route of [ 1246552-90-8 ]

[ 1246552-90-8 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 104-88-1 ]
  • [ 1246552-90-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: sodium cyanide / water; methanol / 20 - 70 °C 2: 6 h / 120 °C / Inert atmosphere 3: ammonia / dichloromethane; water / 0.5 h / -25 °C / Inert atmosphere 4: copper(ll) sulfate pentahydrate / ethanol; water / 0.5 h / Inert atmosphere; Reflux 5: trifluoroacetic acid / ethanol / Inert atmosphere; Reflux 6: trifluoroacetic acid / dichloromethane / 3 h / Inert atmosphere; Reflux 7: sodium nitrite; hydrogen bromide / water / 1.25 h / 0 °C
  • 2
  • [ 667-27-6 ]
  • [ 1246552-90-8 ]
  • [ 1416806-09-1 ]
YieldReaction ConditionsOperation in experiment
42% With bronze powder In dimethyl sulfoxide for 16h; Inert atmosphere; 15 To a stirred suspension of Copper-Bronze (1.52 g, 8.25 mmol) in DMSO (10 mL) was added ethyl 2-bromo-2,2-difluoroacetate (0.55 mL, 4.13 mmol) at RT. After being stirred at RT for 1 h, compound AE (0.5 g, 2.06 mmol) was added portionwise, and the mixture was stirred for 16 h under inert atmosphere. After completion of reaction (by TLC), the reaction mixture was quenched with satd NH4Cl solution (50 mL), filtered through a Celite pad and washed with CH2Cl2 (3×50 mL). The separated organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (eluting with 5-10% EtOAc in hexanes) to afford ester AF (0.25 g, 0.87 mmol, 42%) as a thick syrup. 1H NMR (500 MHz, CDCl3): δ 9.20 (s, 1H), 8.12 (s, 1H), 8.03 (s, 1H), 7.91 (d, J=8.5 Hz, 1H), 7.75 (d, J=8.5 Hz, 1H), 4.38 (q, J=7.0 Hz, 2H), 1.33 (t, J=7.0 Hz, 3H). MS (ESI): m/z 286 [M+H]+.
  • 3
  • 7-chloroisoquinolin-3-amine [ No CAS ]
  • [ 1246552-90-8 ]
YieldReaction ConditionsOperation in experiment
22% With hydrogen bromide; sodium nitrite In water at 0℃; for 1.25h; 15 To a stirred solution of amine AD (1.0 g, 5.60 mmol) in 48% aq hydrobromic acid (HBr) solution (4.8 mL) was added sodium nitrite (NaNO2; 0.58 g, 8.40 mmol) in H2O (20 mL) dropwise at 0° C. for 15 min, and the reaction mixture was maintained at the same temperature for 1 h. After completion of reaction (monitored by TLC, 40% EtOAc/hexanes), the reaction mixture was diluted with H2O (20 mL), made basic (pH 8-9) with 2 N aq NaOH solution and then extracted with Et2O (3×30 mL). The combined organic extracts were washed with brine (30 mL), dried over anhydrous Na2SO4 and evaporated in vacuo. The crude material was purified by silica gel column chromatography (eluting with 5-10% EtOAc gradient in hexanes) to afford compound AE (0.3 g, 1.23 mmol, 22%) as an off-white solid. 1H NMR (500 MHz, CDCl3): δ 8.97 (s, 1H), 7.95 (s, 1H), 7.89 (s, 1H), 7.72 (d, J=8.5 Hz, 1H), 7.66 (d, J=8.5 Hz, 1H). MS (ESI): m/z 242 [M+].
  • 4
  • [ 135737-05-2 ]
  • [ 1246552-90-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 6 h / 120 °C / Inert atmosphere 2: ammonia / dichloromethane; water / 0.5 h / -25 °C / Inert atmosphere 3: copper(ll) sulfate pentahydrate / ethanol; water / 0.5 h / Inert atmosphere; Reflux 4: trifluoroacetic acid / ethanol / Inert atmosphere; Reflux 5: trifluoroacetic acid / dichloromethane / 3 h / Inert atmosphere; Reflux 6: sodium nitrite; hydrogen bromide / water / 1.25 h / 0 °C
  • 5
  • [ 135737-02-9 ]
  • [ 1246552-90-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: ammonia / dichloromethane; water / 0.5 h / -25 °C / Inert atmosphere 2: copper(ll) sulfate pentahydrate / ethanol; water / 0.5 h / Inert atmosphere; Reflux 3: trifluoroacetic acid / ethanol / Inert atmosphere; Reflux 4: trifluoroacetic acid / dichloromethane / 3 h / Inert atmosphere; Reflux 5: sodium nitrite; hydrogen bromide / water / 1.25 h / 0 °C
  • 6
  • [ 135737-10-9 ]
  • [ 1246552-90-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: copper(ll) sulfate pentahydrate / ethanol; water / 0.5 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / ethanol / Inert atmosphere; Reflux 3: trifluoroacetic acid / dichloromethane / 3 h / Inert atmosphere; Reflux 4: sodium nitrite; hydrogen bromide / water / 1.25 h / 0 °C
  • 7
  • [ 135737-15-4 ]
  • [ 1246552-90-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trifluoroacetic acid / ethanol / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 3 h / Inert atmosphere; Reflux 3: sodium nitrite; hydrogen bromide / water / 1.25 h / 0 °C
  • 8
  • [ 1416806-08-0 ]
  • [ 1246552-90-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 3 h / Inert atmosphere; Reflux 2: sodium nitrite; hydrogen bromide / water / 1.25 h / 0 °C
  • 9
  • [ 1246552-90-8 ]
  • [ 1416805-63-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: bronze powder / dimethyl sulfoxide / 16 h / Inert atmosphere 2.1: n-butyllithium / hexane; diethyl ether / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C / Inert atmosphere 3.1: diethyl ether / 4 h / 0 - 20 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 20 - 65 °C
  • 10
  • [ 1246552-90-8 ]
  • [ 1416806-10-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bronze powder / dimethyl sulfoxide / 16 h / Inert atmosphere 2.1: n-butyllithium / hexane; diethyl ether / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C / Inert atmosphere
  • 11
  • [ 1246552-90-8 ]
  • [ 1416806-11-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bronze powder / dimethyl sulfoxide / 16 h / Inert atmosphere 2.1: n-butyllithium / hexane; diethyl ether / -78 °C / Inert atmosphere 2.2: 1.25 h / -78 - 20 °C / Inert atmosphere 3.1: diethyl ether / 4 h / 0 - 20 °C
  • 12
  • [ 1246552-90-8 ]
  • (R)-4H-1‘-azaspiro[isoxazole-5,3‘-bicyclo[2.2.2]octan]-3-amine [ No CAS ]
  • N-(7-chloroisoquinolin-3-yl)-4H-1‘-azaspiro[isoxazole-5,3‘-bicyclo[2.2.2]octan]-3-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; 19 j00589j (R)-N-(7-chloroisoquinolin-3 -yl)-4H- 1 ‘-azaspiro[isoxazole-5 ,3 ‘-bicyclo [2.2.21 octanj -3- amine hydrochloride ((R)-19) j00590j To a solution of 3-bromo-7-chloroisoquinoline (0.36 g, 1.5 mmol), compound (R)-A-2 (0.27 g, 1.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.14 g, 0.15 mmol) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.17 g, 0.30 mmol) in dioxane (10 mL) was added cesium carbonate (0.97 g, 3.0 mmol). The mixture was stirred at 100 °C for 16 hours under nitrogen atmosphere, then filtered and concentrated in vacuo. The residue was purified by prep-HPLC [Instmment: GX-B; Column: Welch Ultimate AQ-C18 150x30 mm, particle size: 5 .im; Mobile phase:18-48% acetonitnle in H20 (add 0.1% TFA, v/v)j. The solution was treated with 0.2 M hydrochloric acid and lyophilized to give:Compound (R)-19 (0.22 g, 39% yield) as a yellow solid: cSFC analytical (I) tR=3.896 mm., purity: 100%; LCMS (GG): tR2.032 mi, (ES) m/z (M+H)=343.1; ‘H-NMR (CD3OD, 400 MHz):9.20 (s, 1H), 8.21 (s, 1H), 8.01 (s, 1H), 7.96 (d, J=9.2 Hz, 1H), 7.82 (d, J=8.8 Hz, 1H), 3.79-3.62 (m, 3H), 3.54-3.45 (m, 2H), 3.42-3.38 (m, 3H), 2.46-2.42 (m, 2H), 2.16-2.13 (m, 1H), 2.08-1.94 (m, 2 H).
  • 13
  • [ 1246552-90-8 ]
  • 4H-1‘-azaspiro[isoxazole-5,3‘-bicyclo[2.2.2]octan]-3-amine [ No CAS ]
  • (+/-)-N-(7-chloroisoquinolin-3-yl)-4H-1‘-azaspiro[isoxazole-5,3‘-bicyclo[2.2.2]octan]-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; 19 (+1-) N-(7-chloroisoquinolin-3 -yl)-4H- 1 ‘-azaspiro[isoxazole-5 ,3 ‘-bicyclo [2.2 .2joctanj -3- amine (rae- 19) j00586j To a solution of 3-bromo-7-chloro-isoquinoline (50 mg, 0.21 mmol) and compound raeA-2 (39 mg, 0.21 mmol) in dioxane (2.0 mL) under nitrogen was added tns(dibenzylideneacetone)dipalladium(0) (7.6 mg, 0.083 mmol), 4,5 -bis(diphenylphosphino)-9,9- dimethylxanthene (7.2 mg, 0.0 12 mmol) and sodium tert-butoxide (39 mg, 0.41 mmol). The mixture was stirred at 100 °C for 2 hours, then filtered and concentrated in vacuo. The residue was purified by prep-HPLC [Instrument: GX-B; Column: Phenomenex Synergi-C18 150x30 mm, particle size: 4 pm; Mobile phase: 21-51% acetonitrile in H20 (add 0.1% TFA, v/v)j. The solution was treated with 0.2 M hydrochloric acid and lyophilized to give compound rac-19 (50 mg, 13% yield) as a yellow solid.
  • 14
  • [ 1246552-90-8 ]
  • [ 172975-69-8 ]
  • C17H14ClN [ No CAS ]
YieldReaction ConditionsOperation in experiment
35.5% With potassium phosphate tribasic trihydrate; palladium diacetate In ethanol; water; toluene at 70℃; for 12h; 7 Synthesis of S7-3: 20 mmol S7-1, 30.0 mmol S7-2, 0.20 mmol palladium(II)acetate catalyst and 36 mmol potassium phosphate trihydrate was dissolved in 30 mL of a mixed solvent of toluene:ethanol:water (2:1:2) and heated at 70 ° C for 12 h. It was cooled and extracted with dichloromethane (50 mL×3). The organic phase was collected and purified by silica gel column chromatography eluting with petroleum ether: dichloromethane (10:1). the solid S7 was 37.1 mmol obtained (yield: 35.5%).
  • 15
  • [ 1246552-90-8 ]
  • [ 172975-69-8 ]
  • C21H23N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; potassium phosphate tribasic trihydrate / toluene; ethanol; water / 12 h / 70 °C 2: palladium diacetate; potassium phosphate tribasic trihydrate; triphenylphosphine / toluene / 12 h / Reflux
  • 16
  • [ 1246552-90-8 ]
  • C22H16ClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere 2: tetrahydrofuran / -78 - 20 °C / Inert atmosphere
  • 17
  • [ 1246552-90-8 ]
  • C22H14ClN [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere 2: tetrahydrofuran / -78 - 20 °C / Inert atmosphere 3: formic acid / 120 °C / Inert atmosphere
  • 18
  • [ 1246552-90-8 ]
  • C50H32N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere 2: tetrahydrofuran / -78 - 20 °C / Inert atmosphere 3: formic acid / 120 °C / Inert atmosphere 4: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / Inert atmosphere; Reflux
  • 19
  • [ 1246552-90-8 ]
  • [ 623-49-4 ]
  • C12H10ClNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; 4 Synthesis of Intermediate IM-9 Under an argon atmosphere, add 20.00 g (82.5 mmol) of 3-bromo-7-chloroisoquinoline and 275 mL (0.3 M) of THF to a 500 mL three-necked flask, and while stirring at about -78 ° C, add to 56.7 mL (1.1 equivalents) of a 1.6 mol / L nBuLi / n-hexane solution was added dropwise. After stirring at the same temperature for about 1 hour, 8.99 g (1.1 equivalents, 90.7 mmol) of a THF solution of ethyl cyanoformate (23 mL, 1 mol / L) was added dropwise thereto, and stirred at the same temperature for about 30 minutes. Then, the temperature was raised to room temperature, and stirring was additionally performed. After ensuring that the raw materials disappeared, the reaction solution was cooled with water, and extraction using toluene was performed. The aqueous layer was removed, and the organic layer was washed with aqueous sodium bicarbonate solution and saturated saline solution, and dried over MgSO4. MgSO4 was filtered, and the organic layer was concentrated, and the crude product thus obtained was separated by silica gel column chromatography (using a mixture of hexane and toluene as a developing solvent) to obtain an intermediate IM-9 (17.10 g, yield 88%) .
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