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[ CAS No. 3959-07-7 ] {[proInfo.proName]}

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Product Details of [ 3959-07-7 ]

CAS No. :3959-07-7 MDL No. :MFCD00047931
Formula : C7H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :XRNVSPDQTPVECU-UHFFFAOYSA-N
M.W : 186.05 Pubchem ID :77571
Synonyms :

Calculated chemistry of [ 3959-07-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.82
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 1.92
Log Po/w (WLOGP) : 1.76
Log Po/w (MLOGP) : 2.3
Log Po/w (SILICOS-IT) : 2.13
Consensus Log Po/w : 1.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.63
Solubility : 0.436 mg/ml ; 0.00234 mol/l
Class : Soluble
Log S (Ali) : -2.09
Solubility : 1.51 mg/ml ; 0.00813 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.3
Solubility : 0.0941 mg/ml ; 0.000506 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 3959-07-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3259
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3959-07-7 ]

* 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.

  • Upstream synthesis route of [ 3959-07-7 ]
  • Downstream synthetic route of [ 3959-07-7 ]

[ 3959-07-7 ] Synthesis Path-Upstream   1~5

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  • [ 153171-22-3 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 18, p. 5610 - 5613
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  • [ 68819-84-1 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0 - 20℃; (c) A solution of Boc2O (1.29g, 5.91mmol) in CH2Cl2 (10ml) was added to a suspension of 4-bromobenzylamine (1.00g, 5.38mmol) and Et3N (0.60g, 5.91mmol) in CH2Cl2 (10ml) for 5min at 0°C with a CaCl2 tube. The reaction mixture was stirred overnight at room temperature. Then, H2O (50ml) was added to the mixture, and the organic layer was separated. The aqueous layer was extracted with CHCl3 (50ml×3). The combined organic layer was washed with H2O (50ml×1) and then brine (50ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure to afford (4-bromobenzyl)carbamic acid tert-butyl ester (1.63g, quant. y.) as a colorless solid. Colorless powder (n-hexane). Mp 73–74°C. 1H NMR (300MHz/CDCl3) δ 1.46 (9H, s, t-Bu), 4.26 (2H, d, J=6.0Hz, CH2), 4.84 (1H, br s, NH), 7.16 (2H, d, J=8.4Hz, ArH), 7.45 (2H, d, J=8.4Hz, ArH).
96% With sodium hydroxide In 1,4-dioxane; water at 20℃; for 12 h; / Bromobenzylamine (0.93 g, 5 mmol) was dissolved in 1,4-dioxane (20 mL) and was treated with 10percent aq. NaOH (5 mL). To the stirred solution was added (Boc)20 (1.1 g, 5 mmol) dissolved in dioxane (10 mL). The mixture was stirred at room temperature for 12 hours. Water was added (20 mL) and the reaction mixture was extracted with ethyl acetate (3 x 50 mL). The organic phase was collected, washed with brine, dried over MgS04, filtered, and the solvent was evaporated to give the product as a white solid (1.37 g, 96percent).1H NMR (400 MHz, CDC13) δ (ppm) 7.44 (d, J= 8.1 Hz, 2H), 7.15 (d, J= 8.0 Hz, 2H), 4.86 (br s, 1H), 4.26 (d, J= 6.1 Hz, 2H), 1.45 (s, 9H). ESI-MS (m/z): 287 [M+2]+.
95% at 20℃; for 1 h; A solution of 4-bromobenzylamine (40.0g, 217.0 mmol) in THF (150 mL) was treated with di-tert-butyl dicarbonate (46.0g, 217 mmol) and stirred at rt for 1 h. The reaction mixture was concentrated in vacuo to afford a solid which was purified bychromatography (80:20 Hexanes: EtOAc) afforded the Boc protected amine (63.0 g, 95percent) as a white solid. A solution of the aryl bromide (30.0g, 98.0 mmol) in DMSO (100 mL) was treated with bis(pinacolato)diboron (30.0g, 118 mmol), KOAc (30.0g, 306 mmol), and PdCl2(dppf) (0.2 mmol) and warmed to 85 °C for 12 h. The reaction mixture was diluted with EtOAc (250 mL) and washed with water (2 x 150 mL) and brine (100 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to afford a solid which was purification by chromatography (80:20 hexanes: EtOAc) afforded the desired cmpd (31.0 g, yield 97percent) as a white solid. ESI-MS (M+H)+: 334.
90% at 20℃; Cooling with ice Dissolve 10 mL of p-bromobenzylamine (1.0 g, 5.37 mmol) in a 100 mL round bottom flaskIn dichloromethane (DCM),Further, di-tert-butyl dicarbonate ((Boc) 2O (1.29 g, 5.91 mmol)) was gradually added dropwise.The DCM solution was stirred for 5 minutes under ice salt bath conditions and stirred at room temperature overnight.After the reaction was completed, the solvent was evaporated under reduced pressure, and water (40 mL) was added.The organic layer was combined and dried over anhydrous sodium sulfate.Evaporate the solvent and purify it by silica gel column chromatography. Eluent: petroleumEther (PE) / ethyl acetate (EA) = (20:1),A white solid (1.30 g, 90percent) was obtained.
89% With sodium carbonate In tetrahydrofuran; water for 12 h; Reflux General procedure: p-bromobenzamine (1 g, 5.37 mmol) was dissolved in THF:Water 2:5. Boc2O (1.41 g, 6.45 mmol) and Na2CO3 ( 1.67 g, 12.09 mmol) were then added and the mixture was refluxed for 12 h. Extraction was performed with 3x50 mL of EtOAc. The organic phase was dried with Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography using heptane : EtOAc 10:1. Yield: 1.36 g (89percent, 4.79 mmol). 1H-NMR (CDCl3, 400MHz) δ: 7.74 (dt, 2H), 7.18 (d, 2H), 4.28 (d, 2H), 1.48 (s, 9H). 13C-NMR (CDCl3, 400MHz) δ: 156, 138, 132, 129, 121, 80, 44, 28. GC-MS: 285 m/z. Analytical data can be found in literature.2 Tert-butyl-4-bromobenzylcarbamate (400 mg, 1.40 mmol) was dissolved in 10 mL of dry dioxane, potassium acetate (165 mg, 1.68 mmol), bis(pinacolato)diboron (426 mg, 1.68 mmol) and Pd(dppf)Cl2 (10 mg, 0.01 mmol) were added and the reaction was stirred at 100 ºC for 12 h. The mixture was stirred with 10 mL of sat. NaCl aqueous solution for 10 min. and extracted with 3x50 mL EtOAc. The combined organic phases were dried with Na2SO4 and concentrated in vacuo. The resulting residue was purified by flash chromatography using heptane : EtOAc 10:1. The pure compound was treated with 2.0 M HCl in diethyl ether and the resulting deprotected HCl salt was filtered off. Yield: 276 mg (73percent, 1.039 mmol). 1H-NMR (CDCl3 400MHz) δ: 7.69 (d, 2H), 7.48 (d, 2H), 4.03 (s, 2H), 1.29 (s, 12H). Analytical data can be found in literature.3
89% With triethylamine In dichloromethane at 0 - 20℃; for 1 h; General procedure: To a solution of (6chioropyridin3yl)methanamine (3.30 g, 23.1 mmol) inDCM (30 inL) was added TEA (4.84 mL. 34.7 rnmoi) and BOC2O (6.72 mL, 28.9 mrnol), at 0 °C. The resulting mixture was stirred at ambient temperature for iii. The reaction was quenched with saturated sodium bicarbonate solution (50 mL) and extracted with DCM (3x l0() rnL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain Intermediate 2A (5.50 g, 98.0percent) as a yellow oil. ‘H NMR (300 MHz, DMSO-.ck) ö ppm1.38 (s, 9 H), 4,14 (d, J= 6.04 Hz, 2 H), 7.48 (d, J= 7.93 Hz, 2 H), 771 (dd, J= 8.12,2.46 Hz, I H), 8.28 (d, J = 189 Hz, I H). LCMS ,MethodD): retention time 2.31 mm,jM-H1-{i 243. 1.
78% With triethylamine In dichloromethane at 0 - 20℃; General procedure: The hydrogenation of 3-phenylpropylazide (Table 2, entry 1) is given as an example. 3-Phenylpropylazide (3a) (207.2 mg, 1.29 mmol) was charged into an Ar-filled 100 mL glass autoclave equipped with a Teflon-coated magnetic stirring bar. THF (1.2 mL) degassed by three freeze–thaw cycles was introduced via a Teflon cannula, followed by the addition of a solution of the Pd NPs catalyst in DMF (5.0 mM, 20 μL, 0.10 μmol, S/Pd = 12,900:1). Hydrogen was introduced into the reaction vessel until the pressure gauge indicated 8 atm, and then the pressure was carefully released to 1 atm by opening the stop valve. This procedure was repeated five times,and finally hydrogen was pressurized to 8 atm. The vessel was placed in a water bath controlled at 50 °C, and the reaction mixture was vigorously stirred for 16 h. After careful venting of the hydrogen, the reaction mixture was concentrated under reduced pressure. 1,1,2,2-Tetrachloroethane (124.0 mg, 0.739 mmol) was added as an internal standard for the NMR analysis, and the produced 3-phenylpropylamine (4a) was quantified (99.5percent). The reaction mixture was carefully concentrated under reduced pressure to remove THF. To this crude mixture were added dichloromethane (5 mL) and triethylamine (0.45 mL, 3.2 mmol), and the mixture was cooled to 0 °C. Boc2O (726.7 mg, 3.3 mmol) was added at 0 °C, and the solution was stirred at room temperature over night. The reaction mixture was diluted by addition of dichloromethane (10 mL). The solution was washed 3 times successively with water, then once with brine, and dried over magnesium sulfate. After removal of the drying agent by filtration, the solution was concentrated under reduced pressure. The residual oil was purified by silica gel column chromatography (hexane : ethyl acetate = 20:1), giving pure carbamate Boc-4a as a colorless oil (248.3 mg, 87percent).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3557 - 3560
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3720 - 3731
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8666 - 8670[4] Angew. Chem., 2013, vol. 125, # 33, p. 8828 - 8832,5
[5] Patent: WO2014/85453, 2014, A2, . Location in patent: Page/Page column 58-59
[6] Patent: WO2015/89327, 2015, A1, . Location in patent: Paragraph 0336
[7] Patent: CN108794490, 2018, A, . Location in patent: Paragraph 0056; 0057; 0058
[8] Tetrahedron Letters, 2013, vol. 54, # 3, p. 213 - 216
[9] Patent: WO2018/93569, 2018, A1, . Location in patent: Page/Page column 45; 46; 55
[10] Tetrahedron Letters, 2016, vol. 57, # 37, p. 4183 - 4186
[11] Patent: US2003/199689, 2003, A1, . Location in patent: Page/Page column 48
[12] MedChemComm, 2013, vol. 4, # 12, p. 1562 - 1570
[13] Patent: WO2014/146490, 2014, A1, . Location in patent: Page/Page column 75
[14] Patent: WO2014/146246, 2014, A1, . Location in patent: Page/Page column 63
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Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 5944 - 5948
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  • [ 3959-07-7 ]
  • [ 330794-35-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8666 - 8670[2] Angew. Chem., 2013, vol. 125, # 33, p. 8828 - 8832,5
[3] Patent: WO2015/89327, 2015, A1,
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  • [ 1448189-80-7 ]
Reference: [1] Patent: WO2014/108452, 2014, A1,
[2] Patent: WO2015/867, 2015, A1,
[3] Patent: US2016/45607, 2016, A1,
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