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[ CAS No. 112275-50-0 ] {[proInfo.proName]}

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Chemical Structure| 112275-50-0
Chemical Structure| 112275-50-0
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Product Details of [ 112275-50-0 ]

CAS No. :112275-50-0 MDL No. :MFCD00276987
Formula : C10H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WDPWEXWMQDRXAL-UHFFFAOYSA-N
M.W :200.28 Pubchem ID :2756058
Synonyms :

Calculated chemistry of [ 112275-50-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.31
TPSA : 41.57 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) : 2.5
Log Po/w (XLOGP3) : 0.81
Log Po/w (WLOGP) : 0.46
Log Po/w (MLOGP) : 0.86
Log Po/w (SILICOS-IT) : 0.79
Consensus Log Po/w : 1.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.39
Solubility : 8.08 mg/ml ; 0.0404 mol/l
Class : Very soluble
Log S (Ali) : -1.26
Solubility : 10.9 mg/ml ; 0.0544 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.56
Solubility : 5.5 mg/ml ; 0.0275 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.41

Safety of [ 112275-50-0 ]

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

Application In Synthesis of [ 112275-50-0 ]

* 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 [ 112275-50-0 ]
  • Downstream synthetic route of [ 112275-50-0 ]

[ 112275-50-0 ] Synthesis Path-Upstream   1~8

  • 1
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YieldReaction ConditionsOperation in experiment
90% at 20℃; for 24 h; To a solution of di-tert-butyldicarbonate (2.201 g, 9.780 mmol) in acetic acid (9.8 mL), a solution of 1,4-diazepane (1.0 g, 9.780 mmol) in acetic acid (9.8 mL)at ambient temperature is added. After 24 hours, add water and adjust the pH to 10 with 10percent NaOH. Extract the aqueous phase with dichloromethane (2 x 15 mL), dry the organic phase and eliminate the solvent, to obtain the compound tert-butyl 1,4-diazepane-1-carboxylate with 90.0percent yield.; A liquid is obtained that was analyzed, obtaining the following data: IR νmax (cm-1): 2932, 2514, 1681, 1477, 1411, 1166, 991, 769 ( Figure 4 ).
88% at 20℃; To a solution of 1,4-diazepane (1.00 g, 9.98 mmol) in DCM (22 mL) was added a solution of (t-Boc)2O (1.08 g, 4.99 mmol) in DCM (11 mL) at room temperature.
The reaction mixture was stirred at room temperature overnight and concentrated in vacuo.
The residue was dissolved in Et2O and extracted with 10percent aq. citric acid solution.
The aqueous layer was basified with solid K2CO3 until pH 11 and then extracted with EtOAc twice.
The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to afford tert-butyl 1,4-diazepane-1-carboxylate (795 mg, 88percent) as a yellow oil, which was used for the next reaction without further purification. 1H-NMR (CDCl3, Varian, 400 MHz): δ 1.47 (9H, s) 1.59 (1H, br. s), 1.74-1.80 (2H, m), 2.84-2.93 (4H, m), 3.39-3.51 (4H, m).
66% With triethylamine In dichloromethane c
Homopiperazine-carboxylic Acid tert-butyl Ester
To a solution of homopiperazine (5.0 g, 49.92 mmol) in dichloromethane (100 mL), Di-tert-butyl dicarbonate (3.63 g, 16.64 mmol) and triethylamine (6.96 mL, 49.92 mmol) were added at room temperature.
Then the reaction mixture was stirred at room temperature for 16 hours.
The solid was filtered and the organic phase was washed with water (3*).
The organic phase was dried (sodium sulfate), filtered and concentrated to afford the title compound (6.5 g, 66percent). EI-MS m/z 197.79(M-).
65% at 20℃; for 25 h; Inert atmosphere To a solution of homopiperazine 39 (4.01 g, 39.9 mmol, 2 equiv.) in dry dichloromethane (100 mL) at RT was added a solution of Boc2O (4.37 g, 4.6 mL, 20.0 mmol, 1 equiv.) in dry dichloromethane (50 mL) over a period of 3 h after which the reaction mixture was stirred for 22 h. The solvent was evaporated and the residue thus obtained was treated with water (100 mL). The precipitated product was collected by filtration and the filtrate was further extracted with dichloromethane (3 x 100 mL). The combined organic fractions were dried (Na2SO4) and evaporated to afford the title compound 40 as an opaque, yellow oil (2.60 g, 65percent). The product could be further purified by gradient column chromatography (90:10:0.1 85:15:0.1 v/v CH2Cl2:MeOH:aqueous NH4OH) but was of sufficient purity to be used in the next step without purification. Rf 0.37 (90:10 v/v CH2Cl2:MeOH:aqueous NH4OH); IR (ZnSe) 3319 (NH), 2936, 1677 (C=O), 1413, 1168, 908, 727, 435; 1H NMR (300 MHz, CDCl3) δ 3.48-3.38 (4H, m, NCH2), 2.90-2.83 (4H, m, NHCH2), 2.32 (1H, s, NH), 1.80-1.73 (2H, m, CH2CH2CH2), 1.43 (9H, s, 3 CH3);2, 3 13C NMR (75.5 MHz, CDCl3) δ 155.6 (NCO2t-Bu), 79.4 (C(CH3)3), 49.5 (homopiperaz. CH2), 48.2 (homopiperaz. CH2), 46.1 (homopiperaz. CH2), 45.3 (homopiperaz. CH2), 30.3 (CH2CH2CH2), 28.6 (CH3); HRMS (+ESI) Calc. for C10H20N2O2 [M + H]+ 201.1598, found: 201.1597; m/z (+ESI) 201.20 ([M + H]+, 100percent).
59% at 20℃; for 72 h; [00401] 1. A solution of di-tert-butyl dicarbonate (25 g, 115 mmol.) in CH2Cl2 (100 mL) was added over a period of 20 min to a solution of homopiperazine (57 g, 5.0 equiv) in CH2Cl2 (200 mL). The reaction mixture was stirred at room temperature for 3 days. H2O (150 mL) was added to the reaction mixture and the mixture was extracted with CH2Cl2 (2.x.100 mL). The combined extracts were washed with brine and dried over MgSO4. The solvent was removed under reduced pressure to afford an oil which was purified by simple distillation to give 1-(tert-butyloxycarbonyl)homopiperazine: 13.68 g, 59percent yield, colorless oil: The purity was determined by GC/MS (95percent), m/e 200.1 (M+, C10H20N2O2).
11% at 0℃; for 5 h; Reflux Homopiperazine (5.00 g, 49.92 mmol) was dissolved in methanol (200 ml) and cooled to 0°C. Boc anhydride (12 g, 55.0 mmol) in methanol (100 ml) was added dropwise over 1 h and the reaction allowed to warm to room temperature after which the reaction was heated to reflux for 4 h. The reaction was concentrated in vacuo and dissolved in 1 M citric acid (150 ml). The aqueous layer was then washed with EtOAc (3 x 70 ml). The aqueous layer was then cooled to 0°C made basic with solid Na2C03. The product was then extracted with EtOAc (3 100 ml), dried with Na2SO4, filtered and concentrated in vacuo to give WIN-321 -193-01 as a clear oil (1 .08 g, 1 1 percent yield). 1 H N R (CDCI3): δ 3.54 - 3.37 (m, 4H), 2.96 - 2.81 (m, 4H), 1.87 (br. s., 1 H), 1.84 - 1.72 (m, 2H), 1.47 (s, 9H).

Reference: [1] Patent: EP2578588, 2013, A1, . Location in patent: Paragraph 0110; 0111
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 16, p. 6143 - 6148
[3] Patent: US2016/168156, 2016, A1, . Location in patent: Paragraph 0592; 0593
[4] Patent: US2003/216375, 2003, A1,
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 17, p. 5493 - 5497
[6] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 15, p. 7291 - 7301
[7] Patent: EP914319, 2001, B1,
[8] Patent: US6686353, 2004, B1, . Location in patent: Page/Page column 120-121
[9] Tetrahedron Letters, 2008, vol. 49, # 34, p. 5047 - 5049
[10] Journal of the American Chemical Society, 2009, vol. 131, # 40, p. 14413 - 14418
[11] Patent: US6337326, 2002, B1, . Location in patent: Example 1
[12] Patent: WO2017/219083, 2017, A1, . Location in patent: Page/Page column 71; 72
[13] Patent: US2003/153556, 2003, A1,
[14] Patent: US6335324, 2002, B1, . Location in patent: Page column 92
[15] Journal of Medicinal Chemistry, 2011, vol. 54, # 4, p. 1033 - 1058
[16] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2988 - 2998
  • 2
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  • [ 1070-19-5 ]
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YieldReaction ConditionsOperation in experiment
68.9% at 15℃; for 4 h; After homopiperazine 340.0g (3.4mol, 1.5eq), 200mL of ethanol and 50mL of water were mixed, ice water was cooled to 15°C, and then a solution of tert-butyl azide in isopropyl ether was added dropwise thereto. After incubation, the reaction was incubated for 4 h and TLC detected the end of the reaction. After the reaction mixture was concentrated, 200 mL of water was added to stir, and the mixture was filtered. The filtrate was extracted three times with 200 mL of dichloromethane. The combined organic phases were washed once with 200 mL of water and 100 mL of saturated brine in that order, and the organic phase was dried and concentrated to give crude Boc-protected homopiperazine. 250 mL of petroleum ether was added to the crude product and stirred. The solid was washed with ice-cold salt and dried. After suction drying, a single Boc-protected homopiperazine was obtained. The yield was 313.2 g, and the GC purity was 97.2percent. The yield is 68.9percent.
Reference: [1] Patent: CN106810467, 2017, A, . Location in patent: Paragraph 0020; 0044; 0046
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Reference: [1] Patent: US6262046, 2001, B1,
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Reference: [1] Patent: US5380724, 1995, A,
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Reference: [1] Patent: WO2003/101994, 2003, A1, . Location in patent: Page 84
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Reference: [1] Patent: EP574906, 1993, A2,
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Reference: [1] Patent: US6337326, 2002, B1, . Location in patent: Page column 6
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  • [ 223796-20-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 11, p. 2217 - 2226
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