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[ CAS No. 65996-58-9 ] {[proInfo.proName]}

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Chemical Structure| 65996-58-9
Chemical Structure| 65996-58-9
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Product Details of [ 65996-58-9 ]

CAS No. :65996-58-9 MDL No. :
Formula : C6H6N4O Boiling Point : -
Linear Structure Formula :- InChI Key :FFYPRJYSJODFFD-UHFFFAOYSA-N
M.W : 150.14 Pubchem ID :135461003
Synonyms :

Calculated chemistry of [ 65996-58-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 3.0
Molar Refractivity : 41.12
TPSA : 87.56 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) : -7.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.18
Log Po/w (XLOGP3) : -0.76
Log Po/w (WLOGP) : -0.16
Log Po/w (MLOGP) : -0.53
Log Po/w (SILICOS-IT) : 1.0
Consensus Log Po/w : -0.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.9
Solubility : 19.0 mg/ml ; 0.127 mol/l
Class : Very soluble
Log S (Ali) : -0.6
Solubility : 37.6 mg/ml ; 0.25 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.07
Solubility : 1.28 mg/ml ; 0.00855 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 65996-58-9 ]

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 [ 65996-58-9 ]

* 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 [ 65996-58-9 ]
  • Downstream synthetic route of [ 65996-58-9 ]

[ 65996-58-9 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 224946-82-1 ]
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YieldReaction ConditionsOperation in experiment
99% With ammonium formate In methanol at 75℃; for 4 h; 2-Amino-3H-pyrrolo[3,2-0C for 4 h. After completion of the reaction, the reaction mixture was cooled and filtered through a pad of Celite with hot 1 : 1 DMF/MeOΗ. The filtrate was concentrated in vacuo to provide the product as an off-white solid (6.2 g, 99percent).
Reference: [1] Patent: WO2006/122003, 2006, A2, . Location in patent: Page/Page column 32; 36
  • 2
  • [ 570386-22-0 ]
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YieldReaction ConditionsOperation in experiment
61% With sodium dithionite In water for 2 h; Heating / reflux A mixture of 10 (24 g) and sodium dithionite (48 g) in water (240 ml) was heated under reflux for 2 h..
The suspension was hot filtered, cooled and then filtered to give 2 (7.84 g, 61percent) as a yellow/brown solid..
Recrystallized from water it had mp>300° C. 1H NMR (d6-DMSO) was as reported.3 13C NMR δ 155.9, 152.0, 146.6, 128.3, 113.6, 101.2.
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 22, p. 8411 - 8412
[2] Patent: US6693193, 2004, B1, . Location in patent: Page column 11-12; 16
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  • [ 518316-55-7 ]
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Reference: [1] Synthetic Communications, 2002, vol. 32, # 24, p. 3797 - 3802
[2] Croatica Chemica Acta, 2008, vol. 81, # 1, p. 147 - 156
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YieldReaction ConditionsOperation in experiment
9.6%
Stage #1: With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 26℃;
Stage #2: With sodium acetate In methanol at 0 - 20℃;
Stage #3: With sodium hydroxide In methanol; water at 60℃; for 0.5 h;
Preparation of Intermediate DDTo a mixture of Intermediate CC (200 mg, 1.049 mmol), Et3N (0.436 mL, 3.14 mmol), and l ,3-dicarbomethoxy-2-methyl-2-thiopseudourea (216 mg, 1.049 mmol) in DMF (8 mL) was added HgCl2 (284 mg, 1.049 mmol) at room temperature (26 °C). The mixture was stirred overnight. The reaction mixture was then filtered, and the filtrate was diluted with H20 (50 mL), extracted with EtOAc (-150 mL), washed with H20 (50 mL) and brine solution (50 mL), dried (Na2SC>4), filtered, and evaporated to obtain crude Intermediate DD (150 mg). This material was used in the next step without any further characterization and purification. Rf = 0.3 (20percentEtO Ac/petroleum ether). Mass: (m z=313.1).Preparation of Compound (33)To a solution of Intermediate DD (150 mg, 0.48 mmol) in MeOH ( 10 mL) was added NaOMe (129 mg, 2.40 mmol) at 0 °C. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was concentrated, and IN aqueous NaOH (2.5 mL) was added. The reaction was heated to 60 °C for 30 minutes. The reaction mixture was evaporated to obtain a crude residue that was purified by column chromatography (100-200 mesh silica gel, 20percent) MeOH/CHCl3/aq. NH3) to obtain Compound (33) (15 mg, 9.6percent). Rf = 0.6 (20percent MeOH/CHCl3/0.1 mL aqueous NH3). 1H-NMR (400MHz, DMSO-J6) δ 11.36 and 1 1.20 (2 overlapped br. s, exchanged with D20, 2H), 7.05 (s, 1H), 6.05 (br. s, exchanged with D20, 2H), 5.88 (d, J = 2.4Hz, 1H). Mass (m/z): 150.7 (M++l). LCMS: (Column: Zodiacsil 120-5-C- 18-Aq (4.6 χ 50 mm), Mobile phase: A: 0.01M HCOONH4 (Aq); B: MeOH, T/percentB: 0/5, 10/90, 10.1/5, Flow: 1.0 mL/min, Diluent: MeOH), Rt=2.379 min, 97.08 (214 nm), 98.26 (254 nm).
Reference: [1] Patent: WO2011/35009, 2011, A1, . Location in patent: Page/Page column 74-75
  • 5
  • [ 111869-50-2 ]
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YieldReaction ConditionsOperation in experiment
701 mg With sodium hydroxide In water for 0.25 h; Microwave irradiation In the sequence, in a microwave tube was added 4 (200 mg,0.97 mmol) and NaOH (195.0 mg, 4.84 mmol) in H2O (5 mL). Theset conditions were 95 C for 15 min with an average power of40 W. This procedure was repeated four times and then the crudeproducts were mixed. The solvent was evaporated under vacuumand then water (5 mL) was added. The mixture was acidified topH 5.0 with glacial acetic acid. The precipitate was filtered andthen recrystallized in ethanol/H2O (3:1) affording the desired product5 in 96percent yield (701.0 mg)
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
  • 6
  • [ 151587-58-5 ]
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Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 29, p. 4595 - 4598
[2] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[3] Patent: US6693193, 2004, B1, . Location in patent: Page column 10-11
  • 7
  • [ 4214-85-1 ]
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Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 22, p. 8411 - 8412
[2] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[3] Tetrahedron Letters, 1993, vol. 34, # 29, p. 4595 - 4598
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[5] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[6] Patent: WO2006/122003, 2006, A2,
  • 8
  • [ 151587-54-1 ]
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Reference: [1] Synthetic Communications, 2002, vol. 32, # 24, p. 3797 - 3802
[2] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[3] Tetrahedron Letters, 1993, vol. 34, # 29, p. 4595 - 4598
  • 9
  • [ 3977-29-5 ]
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Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[4] Patent: WO2006/122003, 2006, A2,
  • 10
  • [ 518316-52-4 ]
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Reference: [1] Synthetic Communications, 2002, vol. 32, # 24, p. 3797 - 3802
  • 11
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Reference: [1] Synthetic Communications, 2002, vol. 32, # 24, p. 3797 - 3802
  • 12
  • [ 518316-53-5 ]
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Reference: [1] Synthetic Communications, 2002, vol. 32, # 24, p. 3797 - 3802
  • 13
  • [ 151587-55-2 ]
  • [ 65996-58-9 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[2] Tetrahedron Letters, 1993, vol. 34, # 29, p. 4595 - 4598
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Reference: [1] Patent: WO2006/122003, 2006, A2,
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Reference: [1] Patent: WO2006/122003, 2006, A2,
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  • [ 914496-92-7 ]
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Reference: [1] Patent: WO2006/122003, 2006, A2,
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  • [ 180059-04-5 ]
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Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 25, p. 4339 - 4340
  • 18
  • [ 180059-05-6 ]
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Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 25, p. 4339 - 4340
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Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 29, p. 4595 - 4598
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  • [ 63200-54-4 ]
Reference: [1] Patent: WO2006/122003, 2006, A2,
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