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Chemical Structure| 68076-36-8
Chemical Structure| 68076-36-8
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Product Details of [ 68076-36-8 ]

CAS No. :68076-36-8 MDL No. :MFCD00210019
Formula : C9H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZFQWJXFJJZUVPI-UHFFFAOYSA-N
M.W : 188.27 Pubchem ID :4351
Synonyms :

Calculated chemistry of [ 68076-36-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 7
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.6
TPSA : 64.35 Ų

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) : -6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 0.7
Log Po/w (WLOGP) : 1.25
Log Po/w (MLOGP) : 0.95
Log Po/w (SILICOS-IT) : 0.55
Consensus Log Po/w : 1.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.99
Solubility : 19.4 mg/ml ; 0.103 mol/l
Class : Very soluble
Log S (Ali) : -1.63
Solubility : 4.42 mg/ml ; 0.0235 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.09
Solubility : 1.52 mg/ml ; 0.00807 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.12

Safety of [ 68076-36-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P312-P363-P405-P501 UN#:2735
Hazard Statements:H314-H303 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 68076-36-8 ]

* 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.

  • Upstream synthesis route of [ 68076-36-8 ]
  • Downstream synthetic route of [ 68076-36-8 ]

[ 68076-36-8 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 24424-99-5 ]
  • [ 110-60-1 ]
  • [ 68076-36-8 ]
YieldReaction ConditionsOperation in experiment
97.65% at 20℃; for 16 h; Synthesis of compound 19: butane diamine (1 g, 0.01 13 mol, 5 eq) was solubilised in CH2CI2 (15 ml). To the solution was added Boc20 (0.619 g, 0.00283 mol, 1 eq) solubilised in CH2CI2 (15 ml). The reaction mixture was left to stir at RT for 16 hours. The structure of the product was evaluated by TLC CH2CI2 8/MeOH 2/NH40aq 33 percent 0.2. The suspension formed was filtered and the filtrate was dried by rotary evaporator. The oily residue was eluted with EtOAc (15 ml) and washed with a saturated NaCI solution (3 χ 10 ml) to remove the excess unreacted diamine. The organic extracts were dehydrated over sodium sulphate and evaporated. 0.520 g of a yellow oil were obtained. Yield 97.65 percent. 1H NMR (400 MHz, CDCI3) δ 1 .38 (s, 9H), 1 .52-1 .59 (m, 4H), 2.34 (brs, 2H, D20 exch.), 2.72- 2.79 (m, 2H), 3.19-3.24 (m, 2H), 5.95 (brs, 1 H, D20 exch.).
97.65% at 20℃; for 16 h; Synthesis of compound 19: butane diamine (1 g, 0.0113 mol, 5 eq) was solubilised in CH2Cl2 (15 ml). To the solution was added Boc2O (0.619 g, 0.00283 mol, 1 eq) solubilised in CH2Cl2 (15 ml). The reaction mixture was left to stir at RT for 16 hours. The structure of the product was evaluated by TLC CH2Cl2 8/MeOH 2/NH4Oaq 33percent 0.2. The suspension formed was filtered and the filtrate was dried by rotary evaporator. The oily residue was eluted with EtOAc (15 ml) and washed with a saturated NaCl solution (3×10 ml) to remove the excess unreacted diamine. The organic extracts were dehydrated over sodium sulphate and evaporated. 0.520 g of a yellow oil were obtained. Yield 97.65percent. 1H NMR (400 MHz, CDCl3) δ 1.38 (s, 9H), 1.52-1.59 (m, 4H), 2.34 (brs, 2H, D2O exch.), 2.72-2.79 (m, 2H), 3.19-3.24 (m, 2H), 5.95 (brs, 1H, D2O exch.).
94.3% at 0 - 20℃; for 21 h; 50.02 g (567.4 mmol) of 1,4-diaminobutane was dissolved in chloroform (600 mL) and was cooled to 0°C. 13.17 g (6.03 mmol) of di-tert-butyl dicarbonate dissolved in chloroform (300 mL) was added drop-wise over the course of two hours and the reaction was stirred overnight, allowing it to reach room temperature. After 21 hours of reaction time, the entire reaction mixture was transferred to a separatory funnel and was washed with water (8 x 200 mL), dried over sodium sulfate and evaporated in vacuo to give 10.71 g (94.3percent yield) of 10 as a clear oil. lH NMR (300 MHz, CDCb) δ 4.84 (s, 1H), 3.04 (t, 2H), 2.64 (t, = 6.7 Hz, 2H), 1.46 - 1.38 (m, 4H), 1.37 (s, 9H). 13C NMR (75 MHz, CDCb) δ 155.93, 78.82, 41.70, 40.30, 30.77, 28.32, 27.37. HRMS (ESI) calculated mass (C9H2iN202) [M+H] 1+: 189.1603, mass found m/z: 189.1601 [M+H] 1+.
83% at 20℃; for 4.5 h; Cooling with ice A solution of di-tert-butyl dicarbonate (22 g, 100 mmol) inMeOH (20 mL) was added over 30 min to a stirred solutionof 1,4-diaminobutane (25, 1.8 g, 20 mmol) in MeOH (160 mL)under ice-cooling. After stirring for 4 h at room temperature,the solvent was removed under reduced pressure. The residuewas purified by silica gel column chromatography (CHCl3:MeOH: aq. NH3=10 : 1 : 0.1) to give the title compound (26)in 83percent yield. Colorless oil. 1H-NMR (CDCl3, 400 MHz) δ:4.68 (1H, br s, NH), 3.11 (2H, q, J=6.7 Hz, NCH2), 2.69 (2H, t,J=6.7 Hz, NCH2), 1.55–1.40 (4H, m, CH2), 1.42 (9H, s, CH3).MS (EI) m/z: 188 [M]+. The 1H-NMR spectrum was similar tothat of a previous report.30
81% With triethylamine In methanol at 0 - 20℃; Inert atmosphere Synthesis of tertiobutyl (4-aminobutyl)carbamoate 2′
4.4 g of 1.4 diaminobutane (0.05 mol) are dissolved in 110 ml of a solution of triethylamine and methanol (10percent by volume of TEA in methanol) under argon and at 0° C. A solution of di-terbutyl dicarbonate (3.63 g, 0.017 mol) and methanol (10 ml) is added dropwise into the mixture under heavy stirring. The mixture is stirred at ambient temperature over one night. The solvents are removed under vacuum to obtain an oily residue which is dissolved in dichloromethane (100 ml) and washed two times with 100 ml of an aqueous solution of sodium hydroxide (10percent by weight of NaOH in water). [0146] The organic phase is dried and rid of solvent under vacuum and the product is purified by chromatography (1:10:89 NH4OH:MeOH:CHCl3). The product 2′ obtained is a translucent oil (yield: 81percent). Rf 0,4 (NH4OH/MeOH/CHCl3). Here Here [0147] NMR1H (300 MHz, CDCL3) δ 4.71 (s, 1H, NHCO), 3.10 (dt, J1=6 Hz, 2H, CH2); 2.69 (t, J1=6 Hz, 2H, CH2); 1.57-1.44 (m, 4H, 2CH2); 1.42 (s, 9H, CH3). [0148] NMR13C (75 MHz, CDCl3) δ 156.2; 79.2; 41.9; 40.8; 30.8, 28.5; 27.6.
79.36% at 20℃; for 13 h; In a 250 ml round bottom flask was added 5 g of butylene diamine (56.72 mol) and dissolved in 50 ml of dichloromethane.15.95 g of di-tert-butyl dicarbonate (56.72 mol) dissolved in 50 ml of methylene chloride were slowly added dropwise to the round bottom flask at room temperature, and the dropwise addition was continued for 1 hour.After the addition was completed, the mixture was stirred at room temperature for 12 hours. After the reaction was completed, with 300ml0.1mol hydrochloric acid,300ml5percent sodium bicarbonate solution, 300ml saturated sodium chloride solution was extracted three times the dichloromethane solution. With anhydrous sodium sulfate The organic phase was dried, then filtered and the organic phase was dried under reduced pressure on a rotary evaporator to give a clear liquid compound 4 (8.46g, yield Rate of 79.36percent).
75% With triethylamine In methanol at 20℃; General procedure: Di-tert-butyl dicarbonate (3.63g, 0.017mol, dissolved in 10mL methanol) was added into a solution of diamine 1a (3.0g, 0.05mol) in triethylamine and methanol (10percent TEA in MeOH, 110mL), and the obtained solution was stirred at room temperature overnight. The methanol and TEA were removed in vacuo to yield an oily residue that was dissolved in dichloromethane (100mL) and washed with a solution of 10percent aq sodium carbonate (2×100mL). The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated to dryness to give translucent oil. The crude product was chromatographed on silica gel (NH4OH:MeOH:CHCl3, 1:10:89) to give 2a as yellow oils (1.91g, 70percent).
75%
Stage #1: With hydrogenchloride In methanol; water at 0℃; for 0.833333 h;
Stage #2: for 70 h;
N-(tert-butoxycarbonyl)-1,4-diaminobutane
Concentrated HCl (2.85 mL, 34.09 mmol) was added to methanol (50 mL) and cooled to 0° C. on ice. 1,4-Diaminobutane (3 g, 34.09 mmol) was added to the mixture and stirred for 20 min.
Water (ddH2O; 7 mL) was added and stirred 30 minutes. Di-tert-butyl dicarbonate (11.72 mL, 51.11 mmol) in methanol (30 mL) was added drop wise over 10 min then stirred for 1 h.
The solvent was evaporated in vacuo and the resulting solid washed with diethyl ether (3*30 mL).
1 M NaOH solution was added and the product was extracted 2* with CH2Cl2.
Both organic layers were combined and washed 1* with a brine solution.
The organic layer was then dried over CaCl2 and concentrated in vacuo to yield a white solid (4.81 g, 75percent yield). ESI [M+H]+1 expected 189.27 Da, observed 189.2 Da. 1H NMR (500 MHz, CDCl3): δ 4.61 (s, 1H), 3.13 (m, 2H), 2.17 (m, 2H), 1.50 (m, 6H), 1.44 (s, 9H).
65.6% With sodium hydroxide In ethanol; water at 20℃; for 12 h; Inert atmosphere To a mixture of 1,4-Diaminobutane (1.30 Kg, 14.75 mol) and aqueous sodiumhydroxide (1.41 L, 10.0 M) was added a solution of di-tert-butyl dicarbonate (1.62Kg, 7.50 mol) in ethanol (14.1 L) dropwise. The mixture was stirred at ambienttemperature for 12 h, and TLC showed that all the diamine were consumed(DCM:MeOH = 5:1, UV). The organic solvent was removed in vacumm, the residuewas diluted with water (4.2 L) and extracted with DCM (3.0 L×3). The organic layerswas combined, washed with brine and dried over Na2SO4. The solvent was removedunder reduced pressure to give the crude product 12 (1.82 Kg, 65.6percent) as yellow oil,which could be used in next step without further purification.
64% With sodium hydroxide In ethanol at 20℃; 20g of butanediamine (compound a) is added into a 500 ml round bottom flask, and added with 23 ml of 28percent sodium hydroxide solution. After butanediamine has been completely dissolved, 200 ml of 12.5percent ethanol solution of (Boc)2O is dropwise added into the reaction solution at room temperature while agitating. The reaction is carried out under ceaseless agitation at room temperature and monitored via TLC. After reaction is completed, the reaction solution is concentrated by rotary evaporation to remove ethanol, and extracted with DCM for several times until full extraction. The organic layers are merged, washed with saturated salt water, dried with anhydrous sodium sulfate, and treated by suction filtration after standing for some time. After concentration, 13.7 g of compound b, a colorless oil-like substance, is obtained, and the yield is 64percent. The reaction equation is expressed as follows:
64% With sodium hydroxide In ethanol at 20℃; (2) 20 g of butanediamine (compound a) is added into a 500 ml round bottom flask, and added with 23 ml of 28percent sodium hydroxide solution. After butanediamine has been completely dissolved, 200 ml of 12.5percent ethanol solution of (Boc)2O is dropwise added into the reaction solution at room temperature while agitating. The reaction is carried out under ceaseless agitation at room temperature and monitored via TLC. After the reaction is completed, the reaction solution is concentrated by rotary evaporation to remove ethanol, and extracted with DCM for several times until full extraction. The organic layers are merged, washed with saturated salt water, dried with anhydrous sodium sulfate, and treated by suction filtration afier standing for some time. Afier concentration, 13.7 g ofcompound b, a colorless oil-like substance, is obtained, and the yield is 64percent. The reaction equation isexpressed as follows:
60% With sodium hydroxide In ethanol at 20℃; This is a known compound. Ryszard Andruszkiewicz, Michal Radowski, and Zbigniew Czaj gucki; Synthetic Communications, 2005,35: 1085—1094.Sodium hydroxide solution (28percent, 23 mL) was added to 1,4-butanediamine (20 g, compound 4-1) in a 500 mL round bottom flask. After the butanediamine was completelydissolved, di-tert-butylpyrocarbonate [(Boc)20, 200 mL, 12.5percent ethanolic solution] was added dropwise to the reaction solution at room temperature with stirring. After the reaction was completed, the reaction solution was concentrated by rotary evaporation to remove ethanol, and extracted with DCM (6 x 50 mL). The organic layers were combined, neutralized with 2N HC1 to pH 5 and washed with water (2 x 50 mL) and saturated salt water (50 mL) successively toremove the residual butanediamine. The organic phase was then washed with saturated aqueous K2C03 solution and purified by chromatography using a strongly basic alumina column and MeOHIDCM as eluents. After concentration, compound 4-2 was obtained as a colorless oil-like substance (12.8 g, 60percent).
60% at 20℃; for 16 h; General procedure: The appropriate diamine (10 eq) was dissolved in DCM and a solution of Boc2O (1 eq) was added dropwise and the stirring was continued for 16hat room temperature. Removal of the solvent gave residue that was dissolved in DCM and washed with brine (3×10ml). The organic fraction was dried providing the desired products 27 and 28.
55% at 0 - 20℃; for 18 h; General procedure: To a cooled (0°C) suspension of 1,6-diaminohexane (20.0g, 172mmol) in 50mL DCM was added a solution of Boc2O(3.75g, 17.2mmol) in 24mL DCM. After the addition the ice bath was removed and the mixture was stirred at rt for 18h. Afterwards the precipitates were filtered and the filtrate was washed with sat. aqueous NaHCO3(3x50mL). The organic layer was washed with H2O(2x50mL) and brine (50mL), dried over Na2SO4,filtered and concentrated to get 3.1g (84percent) of oil.
8.7% for 12.83 h; Cooling with ice 1,4-diaminobutane (1 mL, 12.94 mmol) was dissolved in DCM (20 mL) and put on ice. Di-tert-butyl dicarbonate (0.3 g, 1.29 mmol) in DCM (5 mL) was dripped in over 50minutes. The reaction was left at ice temperature for 12 hours. The reaction was washed with water (100 mL) followed by brine (100 mL), before being dried with magnesium sulphate. The solvent was removed under vacuum to leave a yellow solid. Yield= 0.087g (8.7percent) lH NMR (CDCb) δ ppm: 1.40- 1.61 (m 12H) 3.13 (q J=6.1 Hz 2H) 4.55 (s 1H) 13C NMR (DMSO) δ ppm: 155.57 (C=0), 77.26 (C), 28.36 (CH3), 28.21, 27.29, 26.93, 26.86. MS (+APCI) m/z= Found 289.2126; expected 188. Diamer produced. IR (KBr) v = 3372 2983 2941 2847 1681 (C=0) 1521 cm"1

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  • 2
  • [ 73371-96-7 ]
  • [ 110-60-1 ]
  • [ 68076-36-8 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: at 0℃; for 18 h;
Stage #2: With hydrogenchloride In water
Stage #3: With sodium hydroxide In water
(a) Protection of 1,4-diaminobutane; 2- (t-Butoxycarbonyloxyimino)-2-phenylacetonitrile (25g) in tetrahydrofuran (75ml, anhydrous) was added dropwise, over 2 hours, to an ice chilled solution of 1,4- diaminobutane 1 (25g) in tetrahydrofuran (75ml, anhydrous). This was allowed to stir for 18 hours. The solvent was removed by evaporation; the crude mixture taken up in water (300ml) and acidified to pH-6 using HCI solution (2M). This was then washed with dichloromethane. The aqueous layer was then basified to -pH 12 with NaOH (2M) and extracted with chloroform (2 x 200ml). The combined organic layers were washed with brine (2 x 150ml), dried (anhydrous sodium sulphate), filtered and evaporated down giving a clear light yellow/green oil 2 (15.1g, -79percent yield) which was sufficiently pure to be carried through to the next stage. Analysis: 1H-NMR (300MHz, CDCl3) 1.16 (2H, br s, -NHz), 1.44 (9H, s, -But), 1.44- 1.54 (4H, m, CH2), 2.71 (2H, m, CH2), 3.13 (2H, m, CH2), 4.70 (lH, br s, NH) ; 13C- NMR (75MHz, CDCl3) 27.48, 28.40, 30.29, 40.43, 41.83, 78.99,155.98; MS (CI) 189 (100percent, M+1).
Reference: [1] Patent: WO2005/116050, 2005, A1, . Location in patent: Page/Page column 29-30
  • 3
  • [ 26364-65-8 ]
  • [ 68076-36-8 ]
Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
  • 4
  • [ 91419-50-0 ]
  • [ 68076-36-8 ]
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  • 5
  • [ 1070-19-5 ]
  • [ 110-60-1 ]
  • [ 68076-36-8 ]
YieldReaction ConditionsOperation in experiment
80.2% at 10℃; for 3 h; 299.2 g (3.4 mol, 1.5 eq) of butylenediamine was mixed with 200 mL of isopropyl ether, cooled in ice water to 10° C., and then isopropyl ether of tert-butyl azidocarboxylate was added dropwise thereto, and the reaction was incubated for 3 hours after completion of the dropwise addition. TLC detected the end of the reaction. The reaction solution was washed successively with 200 mL of water and 100 mL of saturated saline, and the organic phase was dried and concentrated to give crude Boc-protected butylenediamine. Using a vacuum pump to distill off to obtain a colorless transparent liquid, namely a mono-Boc-protected butylenediamine, with a yield of 342.2 g, a GC purity of 98.6percent, and a total yield of 80.2percent in two-step reaction. FIG. 3 is a graph of the results of the nuclear magnetic test of the product.
Reference: [1] Patent: CN106810467, 2017, A, . Location in patent: Paragraph 0038; 0040
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[2] Helvetica Chimica Acta, 1993, vol. 76, # 4, p. 1636 - 1648
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 9, p. 2587 - 2590
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  • 17
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  • 19
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Reference: [1] Synthesis, 1982, # 5, p. 404 - 405
  • 20
  • [ 1538-75-6 ]
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  • [ 68076-36-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4457 - 4478
  • 21
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