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[ CAS No. 222036-66-0 ] {[proInfo.proName]}

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Chemical Structure| 222036-66-0
Chemical Structure| 222036-66-0
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Product Details of [ 222036-66-0 ]

CAS No. :222036-66-0 MDL No. :MFCD10000828
Formula : C8H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :RGJCJWXNNDARPQ-UHFFFAOYSA-N
M.W : 148.16 Pubchem ID :21956239
Synonyms :

Calculated chemistry of [ 222036-66-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.8
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) : -7.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.98
Log Po/w (XLOGP3) : 0.09
Log Po/w (WLOGP) : -0.01
Log Po/w (MLOGP) : 0.52
Log Po/w (SILICOS-IT) : 1.14
Consensus Log Po/w : 0.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.22
Solubility : 8.95 mg/ml ; 0.0604 mol/l
Class : Very soluble
Log S (Ali) : -0.8
Solubility : 23.4 mg/ml ; 0.158 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.459 mg/ml ; 0.0031 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.08

Safety of [ 222036-66-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 222036-66-0 ]

* 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 [ 222036-66-0 ]
  • Downstream synthetic route of [ 222036-66-0 ]

[ 222036-66-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 110568-64-4 ]
  • [ 222036-66-0 ]
YieldReaction ConditionsOperation in experiment
84% With hydrogenchloride; iron In ethanol; water for 2 h; Heating A mixture of 5-nitro-1 lead noise isobutyl ketone Jie (100mg, 0.56mmoL), reduced iron powder (314mg, 5.6mmoL) was added to ethanol (2. OmL) and concentrated hydrochloric acid (0.5mL) and heated under reflux for 2 hours , TLC the reaction was complete. Cooling, the methanol solution saturated with ammonia (NH3) neutralizing the acid, diatomaceous earth filtration, washed with methanol, the solvent evaporated under reduced pressure to give a white solid 70.0mg, 84percent yield
76.2% With hydrogen In methanol for 1 h; Step C / Intermediate B8: 5-aminoisoindoiin-1 -oneTo a solution of 5-nitroisoindolin-1 -one (60 mg, 0.337 mmoi) in methanol (20 mL) was added palladium on carbon (10 percent, 50 mg). The mixture was stirred under an atmosphere of hydrogen for 1 hour. Filtration through Celite, followed by concentration led to 5-aminoisoindoiin-1 -one as a tan solid (38 mg, yield 78.2 percent).
48% With iron; ammonium chloride In ethanol; water at 80℃; for 2 h; Step 4:
Synthesis of 5-Amino-2,3-dihydro-isoindol-1-one
To a suspension of Fe (1.1 g, 19.6 mmole), NH4Cl (1.5 g, 28 mmole) in a mixture of ethanol/water (30 ml/7 ml) at 80° C. was added a mixture of 5-Nitro-2,3-dihydro-isoindol-1-one (1 g, 5.6 mmole) in 10 ml ethanol.
The reaction mixture was stirred at 80° C. for 2 hours.
Mixture was cooled down, filtered off, solid was washed with 50 ml ethanol.
The filtrate was concentrated, taken into 50 ml ethylacetate, washed with 20 ml water.
Organic layer was dried over Na2SO4, filtered and concentrated to give about 900 mg crude.
Trituration with methyl t-butylether gave 400 mg pure product, 48percent yield.
A 18 ml vial was loaded with a mixture of 30percent H2O2 (1 ml), 3N NaOH (3 ml) and MeOH (2.5 ml).
To this mixture 5-Amino-pyridine-2-carbonitrile (450 mg, 3.78 mmole) was added at room temperature.
Reaction mixture was stirred at rt for 45 minutes, TLC showed the starting material to be consumed.
The mixture was diluted with water and filtered; the solid was washed with water and dried to give 480 mg product, 92percent yield.
Reference: [1] Patent: CN103804358, 2016, B, . Location in patent: Paragraph 0126
[2] Patent: WO2012/92880, 2012, A1, . Location in patent: Page/Page column 57
[3] Patent: US9138427, 2015, B2, . Location in patent: Page/Page column 287
[4] Patent: WO2006/17443, 2006, A2, . Location in patent: Page/Page column 154-155
[5] Patent: US2010/15141, 2010, A1, . Location in patent: Page/Page column 26
[6] Patent: WO2011/19538, 2011, A1, . Location in patent: Page/Page column 128
[7] Patent: WO2015/81891, 2015, A1, . Location in patent: Page/Page column 138; 139
  • 2
  • [ 62621-09-4 ]
  • [ 222036-66-0 ]
Reference: [1] Patent: WO2011/19538, 2011, A1,
[2] Patent: WO2015/81891, 2015, A1,
[3] Patent: US9138427, 2015, B2,
[4] Patent: CN103804358, 2016, B,
[5] Patent: WO2012/92880, 2012, A1,
  • 3
  • [ 1113057-04-7 ]
  • [ 222036-66-0 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 11, p. 1815 - 1832
  • 4
  • [ 1975-51-5 ]
  • [ 222036-66-0 ]
Reference: [1] Patent: WO2011/19538, 2011, A1,
[2] Patent: WO2015/81891, 2015, A1,
[3] Patent: US9138427, 2015, B2,
[4] Patent: CN103804358, 2016, B,
  • 5
  • [ 133446-99-8 ]
  • [ 222036-66-0 ]
Reference: [1] Patent: WO2015/81891, 2015, A1,
[2] Patent: US9138427, 2015, B2,
[3] Patent: CN103804358, 2016, B,
[4] Patent: WO2012/92880, 2012, A1,
  • 6
  • [ 1357104-53-0 ]
  • [ 222036-66-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 814 - 819
  • 7
  • [ 552330-86-6 ]
  • [ 222036-66-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 814 - 819
  • 8
  • [ 1357104-48-3 ]
  • [ 222036-66-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 814 - 819
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