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Chemical Structure| 89976-75-0
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Product Details of [ 89976-75-0 ]

CAS No. :89976-75-0 MDL No. :MFCD03425742
Formula : C8H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GEPGYMHEMLZMBC-UHFFFAOYSA-N
M.W : 164.16 Pubchem ID :2763681
Synonyms :

Calculated chemistry of [ 89976-75-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 47.67
TPSA : 64.35 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) : -7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.13
Log Po/w (XLOGP3) : 0.19
Log Po/w (WLOGP) : 0.04
Log Po/w (MLOGP) : -0.06
Log Po/w (SILICOS-IT) : 0.79
Consensus Log Po/w : 0.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.35
Solubility : 7.38 mg/ml ; 0.0449 mol/l
Class : Very soluble
Log S (Ali) : -1.1
Solubility : 13.0 mg/ml ; 0.0795 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.26
Solubility : 0.9 mg/ml ; 0.00548 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.07

Safety of [ 89976-75-0 ]

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 [ 89976-75-0 ]

* 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 [ 89976-75-0 ]
  • Downstream synthetic route of [ 89976-75-0 ]

[ 89976-75-0 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 81721-87-1 ]
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YieldReaction ConditionsOperation in experiment
95% With palladium 10% on activated carbon; hydrogen In methanol for 16 h; To a solution of the compound 7a (2.97g, 15.00 mmol) in MeOH (5OmL) was added palladium 10percent on carbon (0.30g). The resulting mixture was stirred under hydrogen atmosphere for 16 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to afford the compound 7b (2.36g, 95percent) as a brown solid. MS: 165(M+H).
67% With potassium borohydride; copper(l) chloride In methanol at 25℃; To a suspension of 6-nitro-2H-1,4-benzoxazin-3(4H)-one 1 (0.5 g, 0.0026 mol) and CuCl (0.77 g, 0.0078 mol) in anhydrous methanol (25 mL), stirred at 25° C. was added potassium borohydride (0.98 g, 0.018 mol) in portions (exothermic with evolution of hydrogen gas). The reaction mixture was stirred at 25° C. for 30 min. The black precipitate formed was filtered and washed with methanol. The combined filtrate and washings was evaporated to give 6-amino-2H-benzo[b][1,4]oxazin-3(4H)-one which was purified by silica gel column chromatography using ethyl acetate. Brown solid (0.29 g, 67percent). 1H NMR (400 MHz, CDCl3): δ 4.34 (s, 2H); 4.81 (s, 2H); 6.09 (dd, J=2.8, 8.4 Hz, 1H); 6.14 (d, J=2.8 Hz, 1H); 6.59 (d, J=8.4 Hz, 1H); 10.44 (s, 1H).
67% With potassium borohydride; copper(l) chloride In methanol at 25℃; Example 1
6-Amino-2H-benzo[b][1,4]oxazin-3(4H)-one (2) (Scheme 1).
To a suspension of 6-nitro-2H-1,4-benzoxazin-3(4H)-one 1(0.5 g, 0.0026 mol) and CuCl (0.77 g, 0.0078 mol) in anhydrous methanol (25 mL), stirred at 25° C. was added potassium borohydride (0.98 g, 0.018 mol) in portions (exothermic with evolution of hydrogen gas).
The reaction mixture was stirred at 25° C. for 30 min.
The black precipitate formed was filtered and washed with methanol.
The combined filtrate and washings was evaporated to give 6-amino-2H-benzo[b][1,4]oxazin-3(4H)-one which was purified by silica gel column chromatography using ethyl acetate. Brown solid (0.29 g, 67percent). 1H NMR (400 MHz, CDCl3): δ 4.34 (s, 2H); 4.81 (s, 2H); 6.09 (dd, J=2.8, 8.4 Hz, 1H); 6.14 (d, J=2.8 Hz, 1H); 6.59 (d, J=8.4 Hz, 1H); 10.44 (s, 1H).
57.6% With hydrogen In tetrahydrofuran; methanol for 2 h; Reaction 2; A suspension of 1 (3.88g, 20.0mmol) and 5percent Pd/C (200mg) in a mixture of THF (20mL) and MeOH (60mL) was stirred under H2 atmosphere for 2h. The mixture was filtered through celite and the filtrate was concentrated. The residue was purified by column chromatography (MeOH/CHCI3 1:20) to give the product. 2: 1.89g, (57.6percent), gray solid.
56% With hydrogen In methanol 6-Amino-2H-benzo[b][1,4]oxazin-3(4H)-one
Pd/C (10percent) was added to a suspension of 6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (1.5 g) in MeOH (20 mL) and the reaction mixture was stirred under an atmosphere of hydrogen overnight.
The mixture was filtered through Celite.(R). and the filtrate was concentrated under vacuum to give the product (0.705 g, 56percent) as a beige solid.
56% With hydrogen In methanol 6-Amino-2H-benzo[b][1,4]oxazin-3(4H)-one; Pd/C (10percent) was added to a suspension of 6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (1.5 g) in MeOH (20 mL) and the reaction mixture was stirred under an atmosphere of hydrogen overnight. The mixture was filtered through celite and the filtrate was concentrated under vacuum to give the product (0.705 g, 56percent) as a beige solid.

Reference: [1] ChemCatChem, 2014, vol. 6, # 11, p. 3153 - 3159
[2] Patent: WO2018/19252, 2018, A1, . Location in patent: Page/Page column 37
[3] ChemSusChem, 2017, vol. 10, # 15, p. 3035 - 3039
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 71 - 90
[5] Patent: US2009/298819, 2009, A1, . Location in patent: Page/Page column 16; 22
[6] Patent: US2010/216783, 2010, A1, . Location in patent: Page/Page column 14
[7] Patent: WO2005/103018, 2005, A1, . Location in patent: Page/Page column 35
[8] Patent: US2006/194801, 2006, A1, . Location in patent: Page/Page column 49
[9] Patent: US2006/205773, 2006, A1, . Location in patent: Page/Page column 25
[10] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 1263 - 1267
[11] Patent: US5091528, 1992, A,
  • 2
  • [ 598-42-5 ]
  • [ 95-76-1 ]
  • [ 89976-75-0 ]
YieldReaction ConditionsOperation in experiment
98.1% With copper acetylacetonate; sodium hydroxide; N,N`-dimethylethylenediamine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 5 h; Add the appropriate amount of DMF and dichloromethane mixed solvent (30ml) to the reactor.3,4-Dichloroaniline (10 mmol) was added with stirring.Hydroxyacetamide (10 mmol),Copper acetylacetonate catalyst (0.5 mmol),N, N'- dimethylethylenediamine (0.5mmol),NaOH (1 mmol),The reaction is then heated to 50°C for reaction.Reaction 5 hours,TLC detection reaction knot After being bundled, the reaction mixture is poured into saturated saline, stirred rapidly, a large amount of solids precipitate, and filtered and dried to obtain white solid. Body, yield: 98.1percent.
Reference: [1] Patent: CN107652249, 2018, A, . Location in patent: Paragraph 0025-0027; 0037-0046
  • 3
  • [ 85196-33-4 ]
  • [ 89976-75-0 ]
Reference: [1] Patent: JP2018/135315, 2018, A, . Location in patent: Paragraph 0017; 0019
  • 4
  • [ 67-56-1 ]
  • [ 89976-75-0 ]
YieldReaction ConditionsOperation in experiment
95.8% for 0.333333 h; Microwave irradiation A 50 mL round bottom flask was charged with a compound of formula II (0.05 mol)Anhydrous methanol (0.3 mol) and SiO2 supported KNO3 catalyst (2 mmol) were shaken to mix well. The flask was placed in a microwave oven, the flask connected to the condenser outside the furnace, with 100W power microwave radiation reaction, the reaction for 20 minutes. After the reaction was completed, the reaction mixture was poured into a beaker containing 50 mL of ice-NaCl aqueous solution, cooled and solid precipitated. Filtered to give a white solid, yield: 95.8percent.
Reference: [1] Patent: CN107501202, 2017, A, . Location in patent: Paragraph 0019; 0020; 0021; 0031; 0032; 0033-0048
  • 5
  • [ 99-57-0 ]
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Reference: [1] Patent: WO2018/19252, 2018, A1,
  • 6
  • [ 25141-25-7 ]
  • [ 89976-75-0 ]
Reference: [1] Journal of the Chemical Society, 1928, p. 3048
[2] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1957, vol. 15, p. 37
  • 7
  • [ 90814-92-9 ]
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Reference: [1] Gazzetta Chimica Italiana, 1957, vol. 87, p. 659,670
  • 8
  • [ 2298-36-4 ]
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Reference: [1] Chemische Berichte, 1897, vol. 30, p. 2104
  • 9
  • [ 100135-98-6 ]
  • [ 89976-75-0 ]
Reference: [1] Gazzetta Chimica Italiana, 1957, vol. 87, p. 659,670
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