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[ CAS No. 5676-60-8 ] {[proInfo.proName]}

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Chemical Structure| 5676-60-8
Chemical Structure| 5676-60-8
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Product Details of [ 5676-60-8 ]

CAS No. :5676-60-8 MDL No. :MFCD03791181
Formula : C8H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :NNHTUFOCRUBQCF-UHFFFAOYSA-N
M.W : 148.16 Pubchem ID :590539
Synonyms :

Calculated chemistry of [ 5676-60-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.38
TPSA : 52.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 1.48
Log Po/w (WLOGP) : 1.73
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : 1.63
Consensus Log Po/w : 1.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.3
Solubility : 0.749 mg/ml ; 0.00505 mol/l
Class : Soluble
Log S (Ali) : -2.18
Solubility : 0.979 mg/ml ; 0.00661 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.92
Solubility : 0.177 mg/ml ; 0.0012 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.38

Safety of [ 5676-60-8 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H317-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5676-60-8 ]

* 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 [ 5676-60-8 ]
  • Downstream synthetic route of [ 5676-60-8 ]

[ 5676-60-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 5683-43-2 ]
  • [ 5676-60-8 ]
YieldReaction ConditionsOperation in experiment
85% With iron; ammonium chloride In methanol; water at 70℃; for 2 h; INTERMEDIATE Bl2-Methyl- 1 ,3-benzoxazol-6-amine To a heated suspension (70 0C) of 6-nitro-2-methyl-benzoxazole (4.00 g, 22.4 mmol) in MeOH (60 mL) was added a solution of ammonium chloride (12.1 g, 0.227 mol) in water (40 mL) followed by iron powder (4.52 g, 80.1 mmol). The mixture was stirred for 2 h at 70 0C and then filtered through Celite and washed with MeOH. The filtrate was concentrated and the residue was partitioned between water and EtOAc. The organic layers were combined and the solvent was removed under reduced pressure to give the title compound. Yield 2.83 g (85percent). Analytical HPLC: purity 100percent (System A); LRESIMS (ESI+) m/z = 149 (M+H)+.
Reference: [1] Patent: WO2009/150144, 2009, A1, . Location in patent: Page/Page column 137
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 28, p. 5082 - 5088
[3] Journal of the Chemical Society, 1928, p. 121
[4] Journal of the Chemical Society, 1930, p. 2685,2687
[5] DRP/DRBP Org.Chem.,
[6] Patent: US2326497, 1938, ,
[7] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 2640 - 2646[8] Zhurnal Obshchei Khimii, 1960, vol. 30, # 8, p. 2658 - 2664
[9] Collection of Czechoslovak Chemical Communications, 1996, vol. 61, # 2, p. 268 - 275
[10] Collection of Czechoslovak Chemical Communications, 1996, vol. 61, # 3, p. 371 - 380
[11] Tetrahedron Letters, 1999, vol. 40, # 46, p. 8085 - 8088
[12] Patent: US2014/274933, 2014, A1, . Location in patent: Paragraph 0081; 0082
[13] Chemical Communications, 2015, vol. 51, # 91, p. 16312 - 16315
[14] Journal of Photochemistry and Photobiology A: Chemistry, 2018, vol. 361, p. 62 - 66
[15] Patent: US2326497, 1939, ,
  • 2
  • [ 5683-43-2 ]
  • [ 110-54-3 ]
  • [ 7439-89-6 ]
  • [ 5676-60-8 ]
YieldReaction ConditionsOperation in experiment
83% With sodium carbonate In dichloromethane; water; acetic acid; ethyl acetate A.
2-Methyl-6-aminobenzoxazole (479A)
To a solution of 2-methyl-6-nitrobenzoxazole (100 mg, 0.560 mmol) in AcOH (2 mL) was added iron powder (325 mesh, 63.0 mg, 1.12 mmol) at 70° C. in a single portion.
After 15 min at 70° C. additional iron powder (325 mesh, 63.0 mg, 1.12 mmol) was added and stirring was continued for 15 min.
The mixture was cooled and concentrated under reduced pressure.
The resulting residue was taken up into EtOAc and washed with sat. Na2CO3 followed by H2O.
The organic layer was dried over MgSO4, concentrated under reduced pressure and purified by flash chromatography on silica gel eluding with a gradient of 0 to 25percent EtOAc in CH2Cl2 to yield 69 mg (83percent) of compound 479A as a solid. HPLC: 97percent at 0.24 min (retention time) (YMC S5 ODS column, 4.6*50 mm Ballistic, 10-90percent aqueous methanol over 4 min containing 0.2percent H3PO4, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 149.2 [M+H]+.
Reference: [1] Patent: US2004/77605, 2004, A1,
[2] Patent: US2005/119228, 2005, A1,
  • 3
  • [ 13452-14-7 ]
  • [ 5676-60-8 ]
Reference: [1] Patent: EP2589592, 2018, B1,
  • 4
  • [ 95-21-6 ]
  • [ 5676-60-8 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 121
  • 5
  • [ 5676-60-8 ]
  • [ 38191-34-3 ]
Reference: [1] Patent: WO2009/150144, 2009, A1,
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