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Chemical Structure| 72080-83-2
Chemical Structure| 72080-83-2
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Product Details of [ 72080-83-2 ]

CAS No. :72080-83-2 MDL No. :MFCD02094510
Formula : C10H14N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QMMFTRJQCCVPCE-UHFFFAOYSA-N
M.W : 194.23 Pubchem ID :2794257
Synonyms :

Calculated chemistry of [ 72080-83-2 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 53.01
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 0.74
Log Po/w (WLOGP) : 0.72
Log Po/w (MLOGP) : 0.96
Log Po/w (SILICOS-IT) : 0.77
Consensus Log Po/w : 1.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.43
Solubility : 7.19 mg/ml ; 0.037 mol/l
Class : Very soluble
Log S (Ali) : -1.67
Solubility : 4.15 mg/ml ; 0.0214 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.196 mg/ml ; 0.00101 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 72080-83-2 ]

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

Application In Synthesis of [ 72080-83-2 ]

* 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 [ 72080-83-2 ]
  • Downstream synthetic route of [ 72080-83-2 ]

[ 72080-83-2 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 501-53-1 ]
  • [ 107-15-3 ]
  • [ 72080-83-2 ]
YieldReaction ConditionsOperation in experiment
66.5% With potassium carbonate In dichloromethane at -5 - 20℃; for 3 h; Inert atmosphere Under nitrogen protection,To 500 mLAdd three bottlesDichloromethane (100 mL), Ethylenediamine (39 mL, 0.58 mol)And potassium carbonate (32.4 g, 0.23 mol)The reaction temperature is controlled at -5 ~ 0 ,A solution of benzyl chloroformate (20.0 g, 0.12 mol) in dichloromethane (100 mL) was slowly added dropwise with stirring. About 1h dripping is completed,Stir at room temperature for 2h.The reaction was washed with water (200 mL * 2)The organic layer was separated and the organic layer was dried over sodium sulfate (10 g)Concentrated under reduced pressure,Have a pale yellow foam 23.4g.Ethyl acetate (80 mL) was added to the residue,Stir at room temperature until completely dissolved,Slowly add petroleum ether (80 mL) dropwise,A white solid is generated(White solid benzyl formate),Filtration, the mother liquor was concentrated to give a pale yellow oil 15.1g, yield 66.5percent.
1.85 g at 0℃; for 3.5 h; Intermediate 9 Benzyl N-(2-aminoethyl) carbamate A solution of benzylchloroformate ( 1.3 mL, 9 mmol) in DCM (25 mL) was added over 1.5h to a solution of 1,2-diaminoethane (6 mL, 90 mmol) in DCM (95 mL) cooled at 0°C. The solution was stirred for 2h at 0°C, then the solution was washed with brine (40 mL) . The organic phase was filtered through a phase separator and evaporated to dryness to obta in the title compound as a white solid ( 1.85 g) which was used in the next step without further purification. JH NMR (400 M Hz, CDCI3) δ ppm 7.42-7.31 (m, 5H), 5.13 (br s, 3H), 3.27 (dd, 2H), 2.85 (t, 2H) . UPLC-MS : Rt=0.46; m/z (ES+) : 195 [M + H] + .
23 g at 0 - 20℃; For liquid ethylenediamine (147mL, 2.2mol), was dissolved in 500mL dichloromethane. The ice bath was cooled to 0°C, benzyloxycarbonyl chloride dissolved in 1.5L of methylene chloride (30mL, 219mmol) was dissolved was slowly added dropwise to the reaction flask. System was returned to room temperature overnight. The reaction system was filtered, concentrated to remove part of the solvent, washing with water. Finally concentrated to give a pale yellow viscous liquid. After column chromatography to give a clear oily liquid (23g), i.e., compounds 9-3.
Reference: [1] Chemical Communications, 2017, vol. 53, # 52, p. 7088 - 7091
[2] New Journal of Chemistry, 2013, vol. 37, # 7, p. 1895 - 1905
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 550 - 555
[4] Chemistry - A European Journal, 2011, vol. 17, # 19, p. 5251 - 5255
[5] Synthesis, 1984, # 12, p. 1032 - 1033
[6] Patent: CN104557704, 2017, B, . Location in patent: Paragraph 0052; 0053; 0054
[7] Angewandte Chemie, International Edition, 2012, vol. 51, # 40, p. 10060 - 10063,4[8] Angewandte Chemie, 2012, vol. 124, # 40, p. 10207 - 10210,4
[9] Angewandte Chemie - International Edition, 2012, vol. 51, # 40, p. 10060 - 10063[10] Angew. Chem., 2012, vol. 124, # 40, p. 10207 - 10210,4
[11] Helvetica Chimica Acta, 1982, vol. 65, # 6, p. 1853 - 1867
[12] Chemistry Letters, 2007, vol. 36, # 10, p. 1220 - 1221
[13] Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 7, p. 397 - 405[14] Bioorganicheskaya Khimiya, 1994, vol. 20, # 7, p. 740 - 750
[15] Journal of Organic Chemistry, 2007, vol. 72, # 22, p. 8280 - 8289
[16] Patent: WO2013/124286, 2013, A1, . Location in patent: Page/Page column 65
[17] Patent: US2018/99940, 2018, A1, . Location in patent: Paragraph 0658-0664
[18] Patent: CN103450164, 2017, B, . Location in patent: Paragraph 0049; 0053; 0054
  • 2
  • [ 146552-66-1 ]
  • [ 72080-83-2 ]
YieldReaction ConditionsOperation in experiment
90% With triphenylphosphine In methanol; water for 2 h; Reflux Triphenylphosphine(6.7 g, 25.56 mmol) and water (15 mL) were added to asolution of compound 9 (3.8 g, 17.4 mmol) in MeOH(40 mL). The mixture was heated under reflux for 2 h. Themixture was concentrated under reduced pressure andpurified by column chromatography. The target productwas obtained as light brown oil (3 g, 90 percent). 1H NMR(CDCl3, 300 MHz) δ 7.33 (s, 5H), 5.73 (bs, 1H), 5.08 (s,2H), 3.19 (bs, 2H), 2.76 (bs, 2H); 13C NMR (CDCl3,75 MHz) δ 156.8, 136.6, 128.5, 128.0, 66.6, 43.6, 41.5;LC-MS: m/z calculated for C10H14N2O2: 194, Found :195(M+1) +.
Reference: [1] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 10, p. 2854 - 2860
[2] Medicinal Chemistry Research, 2016, vol. 25, # 5, p. 824 - 833
[3] Journal of Chemical Research, Miniprint, 1992, # 12, p. 3117 - 3132
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 12, p. 5769 - 5777
  • 3
  • [ 83019-89-0 ]
  • [ 501-53-1 ]
  • [ 72080-83-2 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With potassium acetate In 1,2-dimethoxyethane; ethanol; water at 20℃; for 1 h;
Example 12; Preparation of N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)-2-hydroxybenzamide (Ic-10); Ethylenediamine (1.0 g, 16.7 mmol) is dissolved in water (3.0 mL) containing bromoaresal green as an indicator. Methane sulfonic acid (2.8 g, 31 mmol) in water (3.0 ml) was added until a blue to pale yellow color transition is just achieved. The solution was diluted with ethanol (8.0 mL) and vigorously stirred. To the mixture was added the solution of Cbz-Cl (2.8 g, 16.7 mmol) in dimethoxyethane (4 mL) and 50percent w/v aqueous AcOK (10 mL) at 20° C. simultaneously to maintain the pale yellow-green color of the indicator. After the additions are complete the mixture was stirred (RT, 1 h) and concentrated at low temperature under vacuum to removed the volatiles. The residue was shaken with water (20 mL) and filtered. The filtrate was then washed with toluene (3.x.50 mL), basified with excess 40percent aqueous NaOH and extracted with toluene (3.x.50 mL). The organic layer was washed with brine (50 mL), dried over Na2SO4 and evaporated to give benzyl 2-aminoethylcarbamate as an oil (1.65 g, 51percent). Mass calculated for C10H14N2O2=194.23; found: [M-H]+=193.3.
Reference: [1] Patent: US2010/41748, 2010, A1, . Location in patent: Page/Page column 115
  • 4
  • [ 18807-71-1 ]
  • [ 72080-83-2 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydrogencarbonate In water Preparation of benzyl (2-aminoethyl)carbamate To a solution of 2-(((benzyloxy)carbonyl)amino)ethanaminium chloride (1.0 g, 4.3 mmol) in water (5 mL) was added anhydrous Na2CO3 until litmus testing indicated pH 9. Solvent removal afforded a residue that was triturated with CH2Cl2 and filtered. The filtrate was concentrated to afford the desired free amine (0.93 g, 99percent yield).
Reference: [1] Patent: WO2015/81282, 2015, A1, . Location in patent: Paragraph 00714; 00715
  • 5
  • [ 13139-17-8 ]
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  • [ 72080-83-2 ]
YieldReaction ConditionsOperation in experiment
80% for 1 h; Step 1
To a solution of 2-aminoethylamine LVIII (150 mL; 2.25 mol) in chloroform (1.5 L), cooled to 0° C. was added a solution of carbobenzoxy N-hydroxysuccinimide (112.14 g; 0.45 mol) in water (0.5 L) with vigorously stirring for one hour.
The solid was filtered and the solution was washed with brine (3*), once with water and dried over anhydrous MgSO4.
The solvent was evaporated under reduced pressure and the residue was purified on a silica gel column (100:1-->30:1 DCM:MeOH) to yield benzyl 2-aminoethylcarbamate LIX as a colorless viscous oil (350 g; 1.80 mol; 80percent yield).
1H NMR (CDCl3) 2.79-2.83 (m, 2H), 3.21-3.28 (m, 2H), 5.10 (s, 2H), 5.19 (brs, 1H), 7.29-7.34 (m, 1H), 7.35-7.38 (m, 4H); ESIMS found for C10H14N2O2 m/z 195.2 (M+H).
Reference: [1] Patent: US2008/318957, 2008, A1, . Location in patent: Page/Page column 57; 58
[2] Chemical Communications, 2011, vol. 47, # 33, p. 9330 - 9332
[3] Organic Letters, 2012, vol. 14, # 17, p. 4450 - 4453
[4] Patent: WO2016/102562, 2016, A1, . Location in patent: Page/Page column 52
  • 6
  • [ 501-53-1 ]
  • [ 115-39-9 ]
  • [ 72080-83-2 ]
YieldReaction ConditionsOperation in experiment
54% With sodium hydroxide; ethylenediamine In methanol; water Step 1
A mixture of ethylenediamine (60 g, 1 mole), water (250 ml), methanol (500 ml) and Bromophenol Blue solution was acidified to pH 3 (yellow color) with hydrochloric acid (165 ml, 12 N).
While the resulting solution was vigorously stirred at 25° C., benzyl chloroformate (100.6 g, 0.59 mole) was added dropwise (addition time 1.75 hours).
Sodium hydroxide (210 ml, 5 N) was added as required to maintain the solution at pH 3.0-4.5.
The methanol was removed at reduced pressure and the reaction mixture was filtered.
The aqueous filtrate was extracted once with benzene, and the benzene extract was discarded.
The aqueous solution was cooled in a salt-ice bath, layered with ether and treated with sodium hydroxide (130 ml, 10 N) to pH 11-13.
Three layers formed:
an ether layer, an aqueous layer, and an oily blue layer.
The aqueous layer was separated and extracted four times with portions of ether.
The ether layer and ether extracts were combined with the oily blue layer and the ether removed using water pump vacuum.
An oil pump was then used at 25° C. until the pressure dropped to 0.6 ppm.
During this time, water and ethylenediamine were removed by distillation.
The residue left in the flask consisted of an oil and a small amount of solid.
After the mixture was filtered, 60 g (54percent yield) of benzyl N-(2-aminoethyl)carbamate were obtained.
This crude oil worked satisfactorily in the next step without further purification.
See C. M.
Hoffmann and S. R. Sapir, Journal of Organic Chemistry, 27, 3565 (1962) for further discussion of this preparatory method.
Reference: [1] Patent: US4346231, 1982, A,
  • 7
  • [ 28170-07-2 ]
  • [ 107-15-3 ]
  • [ 72080-83-2 ]
Reference: [1] Synthesis, 2002, # 15, p. 2195 - 2202
[2] Organic Syntheses, 2007, vol. 84, p. 209 - 214
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 17, p. 2675 - 2685
  • 8
  • [ 77987-49-6 ]
  • [ 72080-83-2 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1992, # 12, p. 3117 - 3132
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 12, p. 5769 - 5777
[3] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 10, p. 2854 - 2860
[4] Medicinal Chemistry Research, 2016, vol. 25, # 5, p. 824 - 833
  • 9
  • [ 134307-72-5 ]
  • [ 72080-83-2 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1992, # 12, p. 3117 - 3132
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 12, p. 5769 - 5777
[3] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 10, p. 2854 - 2860
[4] Medicinal Chemistry Research, 2016, vol. 25, # 5, p. 824 - 833
  • 10
  • [ 886-64-6 ]
  • [ 72080-83-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 3, p. 699 - 709
  • 11
  • [ 501-53-1 ]
  • [ 72080-83-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 12, p. 5769 - 5777
[2] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 10, p. 2854 - 2860
[3] Patent: WO2015/81282, 2015, A1,
[4] Medicinal Chemistry Research, 2016, vol. 25, # 5, p. 824 - 833
  • 12
  • [ 18807-67-5 ]
  • [ 72080-83-2 ]
Reference: [1] Hoppe-Seyler's Zeitschrift fuer physiologische Chemie, 1968, vol. 349, # 2, p. 251 - 262
[2] Israel Journal of Chemistry, 1974, vol. 12, p. 87 - 101
  • 13
  • [ 2304-94-1 ]
  • [ 72080-83-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 3, p. 699 - 709
  • 14
  • [ 100-51-6 ]
  • [ 72080-83-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 17, p. 2675 - 2685
  • 15
  • [ 949-90-6 ]
  • [ 72080-83-2 ]
Reference: [1] Journal of Combinatorial Chemistry, 2010, vol. 12, # 2, p. 248 - 254
  • 16
  • [ 77153-05-0 ]
  • [ 72080-83-2 ]
Reference: [1] Patent: WO2015/81282, 2015, A1,
  • 17
  • [ 3459-92-5 ]
  • [ 107-15-3 ]
  • [ 72080-83-2 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 495
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 496
  • 18
  • [ 72080-83-2 ]
  • [ 18807-71-1 ]
YieldReaction ConditionsOperation in experiment
62.62 g With hydrogenchloride In diethyl ether A solution of N-(benzyloxycarbonyloxy)succinimide (ZOSu, 100 g, 401 mmol) in dichloromethane (500 mL) was added dropwise over 2 hours to a solution ofethylenediamine (1, 189 mL, 2.81 mol) in dichloromethane (750 mL). After 30 minutes the suspension was filtered and solids washed with dichloromethane. The filtrate was evaporated to dryness and the residue diluted with toluene (1.00 L) and water (0.50 L). The resulting mixture was filtered and the filtrate was separated to afford two phases. The aqueous phase contained the product; therefore it was extracted withdichloromethane (2 x 250 mL). All organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was diluted with toluene (750 mL) and extracted with 2 M aqueous hydrochloric acid (500 mL) and 1 M aqueous hydrochloric acid (100 mL). Acidic aqueous phases were combined and basified with a solution of sodium hydroxide (60.0 g, 1.50 mol) in water (90 mL). The resulting mixture was extracted with dichloromethane (4 x 200 mL), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and diluted with hexanes (200 mL). 4 M Solution of hydrogen chloride in ether (100 mL, 400 mmol) was added to the solution, the resulting suspension was concentrated in vacuo and diluted with hexanes (1.00 L). Theprecipitated solid was filtered, washed with hexanes and dried in vacuo to give (2-amino- ethyl)-carbamic acid benzyl ester hydrochloride as white powder.Yield : 62.62 g (68percent).RF (Si02, dichloromethane/methanol 4: 1) : 0.25 (free base).1H NMR spectrum (300 MHz, AcOD-d4, 80 °C, dH) : 7.42-7.26 (m, 5 H); 5.16 (s, 2 H); 3.60 (t, J = 5.7 Hz, 2 H); 3.32 (t, J = 5.7 Hz, 2 H).
Reference: [1] Patent: WO2016/102562, 2016, A1, . Location in patent: Page/Page column 52
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