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[ CAS No. 5414-19-7 ] {[proInfo.proName]}

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Chemical Structure| 5414-19-7
Chemical Structure| 5414-19-7
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Quality Control of [ 5414-19-7 ]

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Product Details of [ 5414-19-7 ]

CAS No. :5414-19-7 MDL No. :MFCD00039196
Formula : C4H8Br2O Boiling Point : -
Linear Structure Formula :O(CH2CH2Br)2 InChI Key :FOZVXADQAHVUSV-UHFFFAOYSA-N
M.W : 231.91 Pubchem ID :21521
Synonyms :
Chemical Name :1-Bromo-2-(2-bromoethoxy)ethane

Calculated chemistry of [ 5414-19-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.17
TPSA : 9.23 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 1.6
Log Po/w (WLOGP) : 1.79
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 1.99
Consensus Log Po/w : 1.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.02
Solubility : 2.21 mg/ml ; 0.00951 mol/l
Class : Soluble
Log S (Ali) : -1.41
Solubility : 9.12 mg/ml ; 0.0393 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.95
Solubility : 0.26 mg/ml ; 0.00112 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.17

Safety of [ 5414-19-7 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P280-P305+P351+P338 UN#:3334
Hazard Statements:H315-H318-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 5414-19-7 ]

* 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 [ 5414-19-7 ]

[ 5414-19-7 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 5414-19-7 ]
  • [ 619-60-3 ]
  • [ 116104-16-6 ]
  • 2
  • [ 5414-19-7 ]
  • [ 66491-03-0 ]
  • [ 183622-29-9 ]
  • 3
  • [ 5414-19-7 ]
  • [ 13130-79-5 ]
  • [ 1179148-99-2 ]
YieldReaction ConditionsOperation in experiment
31% To a stirred solution of <strong>[13130-79-5]3-amino-1-bromoisoquinoline</strong> (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%). Rt=1.75 min (Cond.-MS-WI); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H4BrN2O: 293.03; found: 293.04.
31% To a stirred solution of 3-amino-l-brotaunoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10175 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 0C for 5 min before 2-bromoethyl ether (90%, 250 DL, 2.00 mmol) was added. The mixture was stirred at 25 0C for 5 h and at 75 0C for 72 h before it was cooled to 25 0C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried with Na2SO4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%) . Rt = 1.75 min (Cond. -MS-Wl) ; 90% homogenity index; LCMS: Anal. CaIc. for [M+H] + C13H14BrN2O: 293.03; found: 293.04.
31% To a stirred solution of 3-amino-l-bromoisoquinolirie (444 mg, 2,00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 0C for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred at 25 0C for 5 h and at 75 0C for 72 h before it was cooled to 25 0C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried with Na2SC>;4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond. MS-Wl); 90% homogenity index; LCMS: Anal. CaIc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.
31% With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 25 - 75℃; for 77h; To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2,4 mmol) in one portion. The mixture was stirred at 25C for 5 min before 2- bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred further at 25C for 5 h and at 75 0C for 72 h before it was cooled to 25C} quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO45 filtered and concentrated. Purification of the residue on silica gel elutmg with 0% to 70% ethyl acetate/hexanes afforded Cap- 143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond. MS-Wl); 90% homogenily index; LCMS: Anal. CaIc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.
31% To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2- bromoethyl ether (90%, 250 mu,, 2.00 mmol) was added. The mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2S04, filtered andconcentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond.-MS-Wl); 90% homogenity index; LCMS: Anal. Calc. for [M+H C13H14BrN20: 293.03; found: 293.04.
31% Step a[00254] To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2- bromoethyl ether (90%, 250 mu,, 2.00 mmol) was added. The mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2S04, filtered andconcentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, Step a as a yellow solid (180 mg, 31%). Rt = 1.75 min(Cond.-MS-Wl); 90% homogenity index; LC-MS: Anal. Calc. for [M+H Ci3H14BrN2 293.03; found: 293.04.
31% With sodium hydride; In N,N-dimethyl-formamide; at 25 - 75℃; for 77h; To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2-bromoethyl ether (90%, 250 mu, 2.00 mmol) was added. This mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2S04, filtered and concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes) afforded Cap- 143, step a (180 mg, 31%) as a yellow solid. Rt = 1.75 min (Cond.-MS-Wl); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ Ci3H14BrN20: 293.03; found: 293.04.
31% To a stirred solution of <strong>[13130-79-5]3-amino-1-bromoisoquinoline</strong> (444 mg, 2.00 mmol) in anhydrous dimethylformamide(10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25C for 5 min before 2-bromoethyl ether (90%, 250 mL, 2.00 mmol) was added. This mixture was stirred further at 25 Cfor 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution anddiluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4 filteredand concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes)afforded Cap-143, step a (180 mg, 31%) as a yellow solid. Rt = 1.75 min (Cond.-MS-W1); 90% homogenity index; LCMS:Anal. Calc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.
31% To a stirred solution of <strong>[13130-79-5]3-amino-1-bromoisoquinoline</strong> (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. This mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes) afforded Cap-143, step a (180 mg, 31%) as a yellow solid. Rt=1.75 min (Cond.-MS-W1); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.
To a stirred solution of 3-amino-l-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C for 5 min before 2-bromoethyl ether (90%, 250 L, 2.00 mmol) was added. The mixture was stirred further at 25 C for 5 h and at 75 C for 72 h before it was cooled to 25 C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over a2S04, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap- 143, step a as a yellow solid (180 mg, 31%). Rt = 1.75 min (Cond.-MS-Wl); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ Ci3H14BrN20: 293.03; found: 293.04.

  • 4
  • [ 5414-19-7 ]
  • [ 27489-62-9 ]
  • [ 1228947-14-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In acetonitrile; at 60℃; (0392) Trans-4-Aminocyclohexanol (0.5 g), 1-bromo-2-(2-bromoethoxyl)ethane (1.07 g) and triethylamine (2.42 ml) were dissolved in anhydrous acetonitrile (20 ml). The reaction mixture was heated at 60 C. overnight. The organic solvent was removed under vacuum. The residue was purified with flash column chromatography on silica gel eluting with 7%-10% methanol in dichloromethane to give the title compound.
  • 5
  • [ 5414-19-7 ]
  • [ 63203-48-5 ]
  • [ 1430753-58-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 95℃; Example 160A ethyl 1-morpholinocyclohexanecarboxylate Ethy 1-aminocyclohexancarboxylate hydrogen chloride (5.800 g), triethylamine (13.62 mL) and 1-bromo-2-(2-bromoethoxy)ethane (4.21 mL) were stirred together in N,N-dimethylformamide (50 mL) at 95 C. overnight. The reaction mixture was diluted with ethyl acetate (150 mL), washed with water (100 mL) and brine (100 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with a gradient of 5% to 25% ethyl acetate/hexanes provided the title compound.
  • 6
  • [ 5414-19-7 ]
  • [ 38222-83-2 ]
  • [ 1621534-73-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; acetonitrile; Step 1. Preparation of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bS)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(1-morpholinoethyl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate. In a 20 mL scintillation vial were combined methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bS)-1-(1-aminoethyl)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate TFA salt (0.020 g, 0.019 mmol) with 1-bromo-2-(2-bromoethoxy)ethane (0.00883 g, 0.038 mmol) and triethylamine (0.016 mL, 0.114 mmol) in 1,4-dioxane (0.5 mL). The mixture was heated to 85 degrees C. for 30 min which resulted in no reaction. The mixture was transferred to a 5 mL microwave vessel and was diluted with dry acetonitrile (2 mL). To the mixture was added additional 1-bromo-2-(2-bromoethoxy)ethane (another 10 equivalents; 0.0445 g, 0.190 mmol) as well as <strong>[38222-83-2]2,6-di-tert-butyl-4-methylpyridine</strong> (0.023 g, 0.114 mmol). The resulting mixture was heated in the microwave to 120 degrees C. for 90 min. The contents of the vessel were concentrated under nitrogen stream, redissolved with a small quantity of a mixture of THF, acetonitrile and methanol, filtered and purified by reverse phase preparative HPLC (Prep HPLC Method 2). The desired product was thus obtained as a white solid and was carried directly into the next step. LCMS: m/z=778.6 (M+H)+, 2.13 min (method 5).
  • 7
  • [ 5414-19-7 ]
  • [ 36725-28-7 ]
  • C15H19N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; TP5 - To 200 mg (0.984 mmol) of (R)-6-(4-aminophenyl)-5-methyl-4,5- dihydropyridazin-3(2H)-one dissolved in 1 mL of DMF was added 250 (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 mu^ of bis (2-bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product (46%). XH NMR (300 MHz, CDC13) delta 8.61 (s, 1H), 7.68 (d, J= 8.8, 2H), 6.92 (d, J= 8.8, 2H), 3.99 - 3.76 (m, 4H), 3.44 - 3.31 (m, 1H), 3.29 - 3.22 (m, 4H), 2.70 (dd, J= 6.7, 16.8, 1H), 2.46 (d, J= 16.7, 1H), 1.24 (d, J= 7.3, 3H). 13C NMR (75 MHz, CDC13) delta 166.64, 154.05, 152.18, 127.10, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 16.36. MS: 274 (M + 1). Anal. Calcd. for C15H19N3O2: C, 65.91; H, 7.01 ; N, 15.37; Found. 65.81, H, 6.66, N, 15.26.
46% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃;Inert atmosphere; To 200 mg (0.984 mmol) of A dissolved in 1 mL of Dimethylformamide (DMF) was added 250 mu^ (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2C03 and the mixture was stirred overnight at 60 C. The next day another 250 mu^ oi bis (2-bromoethyl) ether and 170 mg of K2C03 were added. After 3 hours, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product (46%). NMR (300 MHz, CDC13) delta 8.61 (s, 1H), 7.68 (d, J = 8.8, 2H), 6.92 (d, J = 8.8, 2H), 3.99 - 3.76 (m, 4H), 3.44 - 3.31 (m, 1H), 3.29 - 3.22 (m, 4H), 2.70 (dd, J = 6.7, 16.8, 1H), 2.46 (d, J = 16.7, 1H), 1.24 (d, J = 7.3, 3H). 13C NMR (75 MHz, CDC13) delta 166.64, 154.05, 152.18, 127.10, 125.33, 114.73, 66.69, 48.33, 33.93, 27.94, 16.36. TLC: Rf 0.1 (1 :50 MeOH:CH2Cl2). HPLC: Rt 1.05 min, purity > 95%. MS: 274 (M + 1). HRMS: calcd. 274.1556 (M + 1); found 274.1552. Anal. Calcd. for G5H19N3O2: C, 65.91 ; H, 7.01; N, 15.37; Found. 65.81, H, 6.66, N,
46% With potassium carbonate; In N,N-dimethyl-formamide; at 602℃;Inert atmosphere; Step 1 ): (0666) To 200 mg (0.984 mmol) of <strong>[36725-28-7](R)-6-(4-aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one</strong> dissolved in 1 mL of DMF was added 250 muIota_ (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 muIota_ of bis (2- bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product Compound 3 (46%). 1H NMR (300 MHz, CDCI3) delta 8.61 (s, 1 H), 7.68 (d, J = 8.8, 2H), 6.92 (d, J = 8.8, 2H), 3.99 - 3.76 (m, 4H), 3.44 - 3.31 (m, 1 H), 3.29 - 3.22 (m, 4H), 2.70 (dd, J = 6.7, 16.8, 1 H), 2.46 (d, J = 16.7, 1 H), 1 .24 (d, J = 7.3, 3H). 13C NMR (75 MHz, CDCI3) delta 1 66.64, 154.05, 152.18, 127.1 0, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 1 6.36. MS: 274 (M + 1 ). Anal. Calcd. for C15H19N3O2: C, 65.91 ; H, 7.01 ; N, 15.37; Found. 65.81 , H, 6.66, N, 15.26.
  • 8
  • [ 5414-19-7 ]
  • [ 4949-69-3 ]
  • 4-(4-iodo-3-methylphenyl)morpholine [ No CAS ]
  • 9
  • [ 5414-19-7 ]
  • [ 21230-43-3 ]
  • ethyl 1-methyl-3-morpholino-1H-pyrazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With caesium carbonate; In N,N-dimethyl acetamide; at 120℃; A solution of the <strong>[21230-43-3]ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate</strong> (500 mg, 2.95 mmol), C52CO3 (2.9 g, 8.87 mmol), 1-bromo-2-(2-bromoethoxy) ethane (1.37 g, 5.90 mmol) in DMA(lOmL) as stirred at 120C overnight. Then H20 (20 mL) was added to the mixture and it was extracted with EA(x3). The organic layer was dried and purified by flash to give desired compound as yellow oil (610 mg, 87%). ESI-MS m/z: 240.0 [M+Hjt
87% With caesium carbonate; In N,N-dimethyl acetamide; at 120℃; A solution of the <strong>[21230-43-3]ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate</strong> (500 mg, 2.95 mmol), Cs2CO3 (2.9 g, 8.87 mmol), 1-bromo-2-(2-bromoethoxy) ethane (1.37 g, 5.90 mmol) in DMA (10mL) as stirred at 120 oC overnight. Then H2O (20 mL) was added to the mixture and it was extracted with EA(x3). The organic layer was dried and purified by flash to give desired compound as yellow oil (610 mg, 87%). ESI-MS m/z: 240.0 [M+H]+.
  • 10
  • [ 5414-19-7 ]
  • [ 56239-26-0 ]
  • [ 1228947-14-5 ]
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; ;