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[ CAS No. 1068-57-1 ] {[proInfo.proName]}

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Product Details of [ 1068-57-1 ]

CAS No. :1068-57-1 MDL No. :MFCD00007610
Formula : C2H6N2O Boiling Point : -
Linear Structure Formula :H2NN(H)C(CH3)O InChI Key :OFLXLNCGODUUOT-UHFFFAOYSA-N
M.W : 74.08 Pubchem ID :14039
Synonyms :

Calculated chemistry of [ 1068-57-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 17.44
TPSA : 55.12 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) : -7.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.56
Log Po/w (XLOGP3) : -1.58
Log Po/w (WLOGP) : -1.0
Log Po/w (MLOGP) : -0.96
Log Po/w (SILICOS-IT) : -1.22
Consensus Log Po/w : -0.84

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.76
Solubility : 428.0 mg/ml ; 5.78 mol/l
Class : Highly soluble
Log S (Ali) : 0.93
Solubility : 632.0 mg/ml ; 8.53 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.23
Solubility : 124.0 mg/ml ; 1.68 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 1068-57-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P201-P202-P264-P270-P280-P301+P310+P330-P302+P352-P305+P351+P338-P308+P313-P332+P313-P337+P313-P405-P501 UN#:2811
Hazard Statements:H301-H315-H319-H341-H351 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1068-57-1 ]

* 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 [ 1068-57-1 ]
  • Downstream synthetic route of [ 1068-57-1 ]

[ 1068-57-1 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 56-81-5 ]
  • [ 20845-34-5 ]
  • [ 39986-37-3 ]
  • [ 2786-22-3 ]
  • [ 75-07-0 ]
  • [ 64-19-7 ]
  • [ 3332-08-9 ]
  • [ 802294-64-0 ]
  • [ 1068-57-1 ]
  • [ 107-18-6 ]
  • [ 116-09-6 ]
  • [ 107-02-8 ]
  • [ 17167-73-6 ]
  • [ 68078-09-1 ]
Reference: [1] Catalysis Science and Technology, 2014, vol. 4, # 9, p. 3090 - 3098
  • 2
  • [ 62-55-5 ]
  • [ 1068-57-1 ]
  • [ 7343-34-2 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 11, p. 2492 - 2495
  • 3
  • [ 60-35-5 ]
  • [ 1068-57-1 ]
  • [ 7343-34-2 ]
Reference: [1] Journal of the Chemical Society, 1900, vol. 77, p. 1190
  • 4
  • [ 73818-55-0 ]
  • [ 1068-57-1 ]
  • [ 13148-65-7 ]
Reference: [1] Synlett, 1997, vol. 1997, # 3, p. 283 - 284
  • 5
  • [ 1068-57-1 ]
  • [ 78-39-7 ]
  • [ 13148-65-7 ]
Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 3442 - 3444
  • 6
  • [ 506-68-3 ]
  • [ 1068-57-1 ]
  • [ 52838-39-8 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1975, vol. 11, p. 1272 - 1277[2] Khimiya Geterotsiklicheskikh Soedinenii, 1975, vol. 11, # 11, p. 1493 - 1498
  • 7
  • [ 2290-65-5 ]
  • [ 1068-57-1 ]
  • [ 108-33-8 ]
Reference: [1] RSC Advances, 2013, vol. 3, # 19, p. 6813 - 6816
  • 8
  • [ 79-20-9 ]
  • [ 1068-57-1 ]
  • [ 3069-67-8 ]
YieldReaction ConditionsOperation in experiment
99% at 0℃; Sealed tube; Green chemistry; Large scale (2) Preparation of oxadiazolone:Methyl acetate 2000ml into 5000ml three bottles,Under stirring, 740 g of acetylhydrazine was added,Frozen down to 0 below, put 1680g sodium bicarbonate,Seal the reaction bottle.To the reaction bottle in the continuous access to phosgene, phosgene flow rate of 15m3 / h.After the end of the reaction, the solvent was distilled off, crystallized at 0 ° C and filtered to give a white solid 988.2 g, yield: 99percent.
Reference: [1] Patent: CN103724327, 2017, B, . Location in patent: Paragraph 0008; 0030; 0032
  • 9
  • [ 1068-57-1 ]
  • [ 3069-67-8 ]
Reference: [1] Patent: US4952701, 1990, A,
  • 10
  • [ 75-44-5 ]
  • [ 1068-57-1 ]
  • [ 3069-67-8 ]
Reference: [1] Chemische Berichte, 1949, vol. 82, p. 121
[2] Yakugaku Zasshi, 1956, vol. 76, p. 1304,1306, 1307[3] Chem.Abstr., 1957, p. 4275
[4] Helvetica Chimica Acta, 1972, vol. 55, p. 1174 - 1178
[5] Patent: US4952701, 1990, A,
  • 11
  • [ 32315-10-9 ]
  • [ 1068-57-1 ]
  • [ 3069-67-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4430 - 4448
  • 12
  • [ 1068-57-1 ]
  • [ 503-38-8 ]
  • [ 3069-67-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 5, p. 1603 - 1606
[2] Patent: CN106632127, 2017, A, . Location in patent: Paragraph 0001-0003
  • 13
  • [ 1068-57-1 ]
  • [ 103-70-8 ]
  • [ 16227-12-6 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1929, vol. <2> 120, p. 63
  • 14
  • [ 603-69-0 ]
  • [ 35691-93-1 ]
  • [ 141-97-9 ]
  • [ 1068-57-1 ]
Reference: [1] Russian Journal of Organic Chemistry, 1994, vol. 30, # 10, p. 1630 - 1636[2] Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 10, p. 1548 - 1553
[3] Russian Journal of Organic Chemistry, 1994, vol. 30, # 10, p. 1630 - 1636[4] Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 10, p. 1548 - 1553
[5] Russian Journal of Organic Chemistry, 1994, vol. 30, # 10, p. 1630 - 1636[6] Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 10, p. 1548 - 1553
  • 15
  • [ 1068-57-1 ]
  • [ 556-61-6 ]
  • [ 38942-50-6 ]
YieldReaction ConditionsOperation in experiment
38.9%
Stage #1: for 6 h; Heating / reflux
Stage #2: With sodium hydroxide In ethanol; water for 1 h; Heating / reflux
Acetic hydrazide (7.4 g, 100 mmol) in ethanol (75 mL) was placed in a 200 mL 3-necked round bottomed flask outfitted with a magnetic stir bar and a reflux condenser. Methyl isothiocyanate (7.3 g, 100 mmol) in ethanol (75 mL) was added to the pot. The mixture was refluxed, under N2, for 6 h. The reaction was cooled to room temperature and the solvent removed on the rotovap. The resulting wet solid was triturated with ether and filtered to give a sticky, yellow solid. This solid was triturated with hot CH2Cl2/ethyl acetate (1:1), which afforded a white solid of the uncyclized intermediate. The solid and all liquids associated with the reaction were combined, dissolved in ethanol. Aqueous NaOH (1 M, 50 mL) was added and the mixture refluxed under N2 for 1 h. Acetic acid was used to acidify to a pH of 4-5. The mixture was then cooled on an ice bath to facilitate precipitation. White solid formed, was filtered and washed with ether. (repeated the crystallization process three times with mother liquors). Combined all solids collected and chromatographed through silica gel, eluting with 14percent MeOH/ethyl acetate. The collected fractions were concentrated, washed with ether and filtered to yield 5.02 g (38.9percent) of the desired product. 1H NMR (DMSO-d6): d 2.27 (s, 3H) 3.37 (s, 3H) 13.36 (broad s, 1H). MS (APCI) calcd for C4H7N3S: 129.18; found (M+H+) 130.0.
Reference: [1] Patent: US2005/176701, 2005, A1, . Location in patent: Page/Page column 214
  • 16
  • [ 1068-57-1 ]
  • [ 149-73-5 ]
  • [ 3451-51-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 8, p. 1268 - 1285
[2] Patent: WO2011/88025, 2011, A1, . Location in patent: Page/Page column 48; 51
  • 17
  • [ 2290-65-5 ]
  • [ 1068-57-1 ]
  • [ 2302-88-7 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5238 - 5242
[2] RSC Advances, 2013, vol. 3, # 21, p. 7684 - 7687
  • 18
  • [ 100-70-9 ]
  • [ 1068-57-1 ]
  • [ 25433-36-7 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With sodium methylate In methanol at 20℃; for 1 h;
Stage #2: for 10 h; Reflux
General procedure: 5 ml of sodium methoxide methanolic solution (35 wtpercent) was added to a solution of 2-cyanopyridine (0.05 mol) in20 ml of methanol and stirred at room temperature for 1 h. Then the respective hydrazide was added to the generate dimino ester solution and refluxed for 10 h. The obtained mixture was cooled to room temperature and the solvent removed in vacuo. The resulting residue was diluted with water and acidified with 2 ml of acetic acid to produce a white solid. The crystals were separated via filtration, dried and recrystallized from toluene (HL1–3). The physical properties and analytical data of compounds HL1-3 are listed in Table 1, and the spectral data of compounds HL1-3are listed in Table 2.
Reference: [1] Chemical Papers, 2017, vol. 71, # 10, p. 2003 - 2009
  • 19
  • [ 1068-57-1 ]
  • [ 4755-77-5 ]
  • [ 869108-50-9 ]
Reference: [1] Patent: EP1748048, 2007, A1, . Location in patent: Page/Page column 39
  • 20
  • [ 1068-57-1 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
YieldReaction ConditionsOperation in experiment
82 % ee at 20 - 90℃; for 2 h; In a 500mL two neck round-bottomed flask equipped with a magnetic stir bar was dissolved amide 5 (3.40g, 8.13mmol) in THF (60mL) and cooled to −78°C. While stirring at −78°C, potassium tert-butoxide (1.0M solution in THF, 8.95mL, 8.94mmol, 1.10equiv) was added. The reaction mixture was warmed to −10°C and stirred for 30min. The reaction mixture was cooled to −78°C and diphenyl chlorophosphate (2.02mL, 9.76mmol) was added to the reaction mixture. The resulting mixture was warmed to −10°C and stirred at this temperature for 45min. Acetylhydrazide (0.90, 12.20mmol, 1.50equiv) was added to the reaction mixture. The reaction mixture was stirred at room temperature. After 1h, 1-butanol (70mL) was added to the reaction mixture, which was heated to 90°C. After 1h, all solvents were removed under reduce pressure. The residue was dissolved in CH2Cl2 and washed with saturated aq. NaHCO3, brine, dried over anhydrous Na2SO4 and concentrated in vacuo to obtain crude (+)-JQ1, which was purified by flash column chromatography on silica gel (0–100percent ethyl acetate in hexanes) to afford (+)-JQ1 (3.04g, 82percent) as a white solid and with a 91:9 er (determined with Supercritical Fluid Chromatography (SFC) using the CHIRALPAK AS-H column, CO2–EtOH (3:1), 210nm, tR (R-enantiomer) 1.62min, tR (S-enantiomer) 3.51min). This product was further purified by preparative SFC using a CHIRALPAK AS-H column to obtain (+)-JQ1 (S-enantiomer) with >99percent ee. The spectral data of (+)-JQ1 matched with those described in the literature6 with the exception of the optical rotation. [α]D22 +41 (c 0.50, CHCl3), (Lit. [α]D22 +55 (c 0.50, CHCl3);12 (−)-JQ1: >99percent ee, [α]D22 −39 (c 0.55, CHCl3), (Lit. [α]D22 −55 (c 0.50, CHCl3).6
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 21
  • [ 1268524-67-9 ]
  • [ 1068-57-1 ]
  • [ 1268524-70-4 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran at -78 - 23℃; for 0.5 h;
Stage #2: With diethyl chlorophosphate In tetrahydrofuran at -10℃; for 0.75 h;
Stage #3: at 23 - 90℃; for 2 h;
Potassium tert-butoxide (1.0 M solution in THF, 0.3 ml, 0.30 mmol, 1.10 equiv) was added to a solution of S5 (114 mg, 0.27 mmol, 1 equiv) in THF (1.8 ml, 0.15 M) at -78 °C. The reaction mixture was warmed to -10 °C, and stirred at 23 °C for 30 min. The reaction mixture was cooled to -78 °C. Diethyl chlorophosphate (0.047 ml, 0.32 mmol, 1.20 equiv) was added to reaction mixture 22. The resulting mixture was warmed to -10 °C over 45 min. Acetic hydrazide (30 mg, 0.40 mmol, 1.50 equiv) was added to reaction mixture. The reaction mixture was stirred at 23 °C. After 1 h, 1-butanol (2.25 ml) was added to reaction mixture, which was heated to 90 °C. After 1 h, all solvents were removed under reduce pressure. The residue was purified with flash column chromatography (Combiflash system, 4 g silica gel, gradient 0 to 100 percent ethyl acetate-hexanes) to afford (+)-JQl (114 mg, 92 percent) as white solid with 90 percent enantiomeric purity (determined with Berger Supercritical Fluid Chromatography (SFC) using AS-H column, 85 percent hexanes- methanol, 210 nm, tR (R- enantiomer) = 1.59 min, tR (S-enantiomer) = 3.67 min). The product was further purified by chiral preparative HPLC (Agilent High Pressure Liquid Chromatography using an OD-H column) to provide the S-enantiomer in greater than 99 percent ee.1H NMR (600 MHz, CDC13, 25 °C) δ 7.39 (d, J = 8.4 Hz, 2H), 7.31 (d, J = 8.4 Hz, 2H),4.54 (t, J = 6.6 MHz, 1H), 3.54-3.52 (m, 2H), 2.66 (s, 3H), 2.39 (s, 3H), 1.67 (s, 3H), 1.48 (s, 9H).13C NMR (150 MHz, CDC13, 25 °C) δ 171.0, 163.8, 155.7, 150.0, 136.9, 131.1, 130.9, 130.6, 130.3, 128.9, 81.2, 54.1, 38.1, 28.4, 14.6, 13.5, 12.1.HRMS(ESI) calc'd for C2iH24ClN203S [M+H]+: 457.1460, found 457.1451 m/z.TLC (EtOAc), Rf: 0.32 (UV)[a]22D = + 75 (c 0.5, CHCl3)
Reference: [1] Patent: WO2011/143657, 2011, A1, . Location in patent: Page/Page column 82-83
[2] Patent: WO2017/30814, 2017, A1, . Location in patent: Paragraph 00227
[3] Patent: WO2018/109053, 2018, A1, . Location in patent: Page/Page column 22; 23
  • 22
  • [ 1068-57-1 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
YieldReaction ConditionsOperation in experiment
82 % ee at 20 - 90℃; for 2 h; In a 500mL two neck round-bottomed flask equipped with a magnetic stir bar was dissolved amide 5 (3.40g, 8.13mmol) in THF (60mL) and cooled to −78°C. While stirring at −78°C, potassium tert-butoxide (1.0M solution in THF, 8.95mL, 8.94mmol, 1.10equiv) was added. The reaction mixture was warmed to −10°C and stirred for 30min. The reaction mixture was cooled to −78°C and diphenyl chlorophosphate (2.02mL, 9.76mmol) was added to the reaction mixture. The resulting mixture was warmed to −10°C and stirred at this temperature for 45min. Acetylhydrazide (0.90, 12.20mmol, 1.50equiv) was added to the reaction mixture. The reaction mixture was stirred at room temperature. After 1h, 1-butanol (70mL) was added to the reaction mixture, which was heated to 90°C. After 1h, all solvents were removed under reduce pressure. The residue was dissolved in CH2Cl2 and washed with saturated aq. NaHCO3, brine, dried over anhydrous Na2SO4 and concentrated in vacuo to obtain crude (+)-JQ1, which was purified by flash column chromatography on silica gel (0–100percent ethyl acetate in hexanes) to afford (+)-JQ1 (3.04g, 82percent) as a white solid and with a 91:9 er (determined with Supercritical Fluid Chromatography (SFC) using the CHIRALPAK AS-H column, CO2–EtOH (3:1), 210nm, tR (R-enantiomer) 1.62min, tR (S-enantiomer) 3.51min). This product was further purified by preparative SFC using a CHIRALPAK AS-H column to obtain (+)-JQ1 (S-enantiomer) with >99percent ee. The spectral data of (+)-JQ1 matched with those described in the literature6 with the exception of the optical rotation. [α]D22 +41 (c 0.50, CHCl3), (Lit. [α]D22 +55 (c 0.50, CHCl3);12 (−)-JQ1: >99percent ee, [α]D22 −39 (c 0.55, CHCl3), (Lit. [α]D22 −55 (c 0.50, CHCl3).6
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
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