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Product Details of [ 2615-25-0 ]

CAS No. :2615-25-0 MDL No. :MFCD00075174
Formula : C6H14N2 Boiling Point : -
Linear Structure Formula :- InChI Key :VKIRRGRTJUUZHS-UHFFFAOYSA-N
M.W : 114.19 Pubchem ID :18374
Synonyms :

Calculated chemistry of [ 2615-25-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 34.26
TPSA : 52.04 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) : -7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : -0.32
Log Po/w (WLOGP) : 0.21
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 0.15
Consensus Log Po/w : 0.34

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.35
Solubility : 51.4 mg/ml ; 0.45 mol/l
Class : Very soluble
Log S (Ali) : -0.31
Solubility : 55.7 mg/ml ; 0.488 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.31
Solubility : 55.8 mg/ml ; 0.489 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 2615-25-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3259
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2615-25-0 ]

* 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 [ 2615-25-0 ]
  • Downstream synthetic route of [ 2615-25-0 ]

[ 2615-25-0 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 3114-70-3 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
YieldReaction ConditionsOperation in experiment
30 % de at 200℃; for 2 h; Inert atmosphere; Autoclave In a 500 mL autoclave, 100 g of 1,4-diaminocyclohexane (cis / trans form = 80/20, manufactured by Tokyo Chemical Industry Co., Ltd.), 100 g of propylene glycol monomethyl ether (PGME) 7.5 g of Ru catalyst ("AA-4501", 5percent Ru alumina powder, manufactured by N. E-Chemcat Co., Ltd.) and 0.63 g of sodium methoxide (manufactured by Tokyo Chemical Industry Co., Ltd.) were charged, (N 2) gas (10 kgf / cm 3) was repeated three times, and the inside of the system was replaced with nitrogen gas.While stirring at a stirring speed of 300 rpm, a temperature The reaction was carried out for 2 hours under the condition of 200 ° C. and pressure (pressure of N 2 gas) of 12 MPa. After the reaction, the reaction mixture was cooled to room temperature and pressure filtered using a 0.2 μm membrane filter to remove the catalyst to obtain a filtrate. Analysis of the obtained filtrate by gas chromatography mass spectrometry (GC-MS) revealed that the proportion of cis isomer was 63.37 areapercent, the proportion of trans form was 34.7 areapercent, the other components (4-aminocyclo By-product such as hexanol) was 1.93 areapercent, and cis / trans form = 65/35.
Reference: [1] Patent: JP2015/13833, 2015, A, . Location in patent: Paragraph 0062; 0073
  • 2
  • [ 106-50-3 ]
  • [ 2615-25-0 ]
Reference: [1] Patent: US2175003, 1937, ,
[2] Nippon Kagaku Kaishi, 1941, vol. 62, p. 190,192[3] Chem.Abstr., 1942, p. 5140
[4] Bulletin of the Chemical Society of Japan, 1944, vol. 19, p. 153,154[5] Nippon Kagaku Kaishi, 1941, vol. 62, p. 190,192[6] Chem.Abstr., 1942, p. 5140
[7] Patent: US2175003, 1937, ,
[8] Nippon Kagaku Kaishi, 1941, vol. 62, p. 190,192[9] Chem.Abstr., 1942, p. 5140
[10] Bulletin of the Chemical Society of Japan, 1944, vol. 19, p. 153,154[11] Nippon Kagaku Kaishi, 1941, vol. 62, p. 190,192[12] Chem.Abstr., 1942, p. 5140
[13] Patent: US2175003, 1937, ,
[14] Nippon Kagaku Kaishi, 1941, vol. 62, p. 190,192[15] Chem.Abstr., 1942, p. 5140
[16] Bulletin of the Chemical Society of Japan, 1944, vol. 19, p. 153,154[17] Nippon Kagaku Kaishi, 1941, vol. 62, p. 190,192[18] Chem.Abstr., 1942, p. 5140
  • 3
  • [ 556-48-9 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
Reference: [1] ChemCatChem, 2013, vol. 5, # 10, p. 2905 - 2912
  • 4
  • [ 106-50-3 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
Reference: [1] Russian Journal of Applied Chemistry, 2014, vol. 87, # 3, p. 397 - 403[2] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2014, vol. 87, # 3, p. 397 - 403,7
  • 5
  • [ 106-50-3 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
  • [ 108-91-8 ]
Reference: [1] Russian Journal of Applied Chemistry, 2014, vol. 87, # 3, p. 397 - 403[2] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2014, vol. 87, # 3, p. 397 - 403,7
  • 6
  • [ 100-02-7 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
  • [ 27489-62-9 ]
  • [ 6850-65-3 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 17, p. 3689 - 3693
  • 7
  • [ 106-50-3 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
  • [ 6850-65-3 ]
  • [ 108-91-8 ]
  • [ 108-93-0 ]
Reference: [1] Russian Journal of Applied Chemistry, 2014, vol. 87, # 3, p. 397 - 403[2] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2014, vol. 87, # 3, p. 397 - 403,7
  • 8
  • [ 54657-09-9 ]
  • [ 2615-25-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1977, vol. 20, # 2, p. 279 - 290
  • 9
  • [ 32175-29-4 ]
  • [ 2615-25-0 ]
Reference: [1] Journal of medicinal chemistry, 1965, vol. 8, p. 401 - 404
  • 10
  • [ 106-50-3 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
  • [ 6850-65-3 ]
  • [ 108-91-8 ]
  • [ 108-93-0 ]
Reference: [1] Russian Journal of Applied Chemistry, 2014, vol. 87, # 3, p. 397 - 403[2] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2014, vol. 87, # 3, p. 397 - 403,7
  • 11
  • [ 100-02-7 ]
  • [ 2615-25-0 ]
  • [ 15827-56-2 ]
  • [ 27489-62-9 ]
  • [ 6850-65-3 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 17, p. 3689 - 3693
  • 12
  • [ 24424-99-5 ]
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  • [ 177906-48-8 ]
YieldReaction ConditionsOperation in experiment
83% at 20℃; Example 17. N-(3-(5-((lr,4r)-4-(Dimethylamino)cyclohexylamino)-3-ethylpyrazolo[l,5- ajpyrimidin- 7-ylamino)phenyl)acrylamide (SB1-E-21) tert-Butyl (lr,4r)-4-aminocyclohexylcarbamate (SBl-E-21-1) To a solution of SM-21-1 (2.0 g, 17.5 mmol) in MeOH (100 mL) was added the solution of (Boc)20 (1.1 g, 5.04 mmol) in MeOH (60 mL) dropwise for 30 min, the mixture was stirred at r.t overnight. After completion, concentrated to remove the solvent, the residue was added H20 (50 mL), further stirred at r.t for 20 min, then filtered, the filtrate was extracted with ethyl acetate (120 mL χ 2), the organic phase was washed with brine (50 mL χ 2), dried with Na2S04. Filtered, concentrated to remove the solvent to obtain SBl-E-21-1 (off-white solid, 900 mg, yield 83percent).
66% at 5 - 20℃; (a) terf-Butyl ((l,4-frans)-4-aminocyclohexyl)carbamate (compound 15, Scheme 3, wherein Pq is Boc) In a 10 L reactor, a solution of (l,4-trans)-cyclohexane-l,4-diamine (compound 14, Scheme 3) (89 g, 779 mmol, Aldrich Sigma) in Et20 (2 L) was cooled to 5 °C, then a solution of di-tert-butyl dicarbonate (170 g, 779 mmol) in Et20 (1 L) was added dropwise over 2 h. The reaction mixture was stirred at 5 °C for 2 h and at RT overnight. To the reaction mixture, 10percent citric acid solution (3 L) was added and stirred for 30 min. The insoluble solid was filtered off, and the phases were separated. The aqueous layer was washed with Et20 (1 L). The aqueous phase was cooled to 10 °C and basified with solid NaOH (pH 14), then extracted with DCM (2 x 2 L). The combined organic phases were dried over Na2S04 and evaporated under reduced pressure to give a white solid (110 g, 66percent yield). This was combined with another batch (210 g) of this compound (compound 15) then re-purified by flash column chromatography (2-5percent MeOH/ DCM) to afford a white solid (compound 23) (297 g). *H NMR (400 MHz, CDCI3) δ 4.48 - 4.28 (1H, m), 3.48-3.28 (1H, m) , 2.68 - 2.57 (1H, m) , 2.01 - 1.89 (2H, m) , 1.89 - 1.69 (2H, m), 1.35 (9H, s) and 1.28 - 1.05 (4H, m).
43% at 0 - 20℃; for 16.5 h; Synthesis of Compound 390; terf-Butyl (4-amino-cyclohexyl)-carbamate (223); A solution of irα"^- 1,4-diaminocyclohexane (1 kg, 8.76 mol) in THF (14 L) at 0°C is treated with a solution dicarbonate (238 g, 1.09 mol) in THF (500 mL) over 30 minutes. The reaction mixture is then warmed to RT, stirred 16 h and filtered. The isolated solids are washed with THF (3 x 2 L) and then the filtrate is reduced in vacuo. The residue thus obtained is suspended in water (8 L) and filtered once more. The filtrate is extracted with DCM (3 x 2 L) and the combined organic phases dried over Na2SO4 and reduced in vacuo. The residue is taken up in TBME (2.4 L), washed with water (3 x 300 mL) then concentrated to -400 mL. Heptane (1 L) is added to induce precipitation of the desired amine; the resulting suspension is stirred 1 h at 0°C, filtered and washed with heptane (2 x 100 mL) to afford the title compound. Yield: 100.5 g (43percent).
27.7% at -60 - 20℃; for 13.5 h; To a solution of trans- 1 ,4-diaminocyclohexane (commercially available from Sigma- Aldrich, Milwaukee, WI) (5 g, 43.78mmol) in MeOH (100 mL) was added di-tert-butyl dicarbonate (4.77 g, 21.89 mmol) with MeOH (50 mL) at -60°C over 90 minutes. The temperature was slowly allowed to warm to ambient temperature. The reaction mixture was stirred for 12 hours at ambient temperature. After completion of the reaction, monitored by TLC (TLC eluent: 10percent MeOH in CHC13, Ninhydrin stain active), the reaction mixture was concentrated to remove MeOH. Water was added to form a white precipitate. The resulting mixture was stirred for 10 minutes and then the precipitate was filtered and washed with water. The filtrate (aqueous layer) was extracted with EtOAc (2 x 150mL). The extract was washed with saturated aqueous NaCl solution and separated and further dried on anhydrous Na2S04. Following filtration, the organic layer was concentrated under reduced pressure to afford tert-butyl ((lr,4r)-4-aminocyclohexyl)carbamate as a white solid (2.6 g, 27.70 percent). The filtered solid (3 g) product was bisboc protected compound and unreacted starting material remained in the aqueous layer. FontWeight="Bold" FontSize="10" H NMR (400 MHz, DMSO-d6): δ 6.67 (d, J= 7.6 Hz, 1H), 3.12 (m, 1H), 2.44 (m, 1H), 1.71 (m, 4H), 1.36 (s, 9H), 1.17 (m, 2H), 1.04 (m, 2H).

Reference: [1] Chemistry - An Asian Journal, 2010, vol. 5, # 4, p. 877 - 886
[2] Patent: WO2016/160617, 2016, A2, . Location in patent: Paragraph 00401
[3] Journal of Organic Chemistry, 1996, vol. 61, # 25, p. 8811 - 8818
[4] Patent: WO2016/116563, 2016, A1, . Location in patent: Page/Page column 34-35
[5] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 352
[6] Patent: WO2013/134079, 2013, A1, . Location in patent: Paragraph 0176-0177
[7] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 6, p. 1451 - 1466
[8] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 20, p. 5223 - 5226
[9] Patent: KR2015/83721, 2015, A, . Location in patent: Page/Page column 18
[10] Chemical Communications, 2017, vol. 53, # 6, p. 1064 - 1067
[11] Journal of Enzyme Inhibition and Medicinal Chemistry, 2017, vol. 32, # 1, p. 865 - 877
[12] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 655 - 666
[13] Patent: EP1323710, 2003, A1,
  • 13
  • [ 24424-99-5 ]
  • [ 2615-25-0 ]
  • [ 177906-48-8 ]
Reference: [1] Phytochemistry, 2003, vol. 63, # 3, p. 315 - 334
  • 14
  • [ 24424-99-5 ]
  • [ 2615-25-0 ]
  • [ 195314-59-1 ]
Reference: [1] Patent: US2010/48637, 2010, A1,
  • 15
  • [ 2615-25-0 ]
  • [ 501-53-1 ]
  • [ 149423-77-8 ]
Reference: [1] Patent: WO2015/113455, 2015, A1, . Location in patent: Page/Page column 36
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