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Product Details of [ 619-17-0 ]

CAS No. :619-17-0 MDL No. :MFCD00007262
Formula : C7H6N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :UEALKTCRMBVTFN-UHFFFAOYSA-N
M.W : 182.13 Pubchem ID :12076
Synonyms :

Calculated chemistry of [ 619-17-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 46.63
TPSA : 109.14 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) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.15
Log Po/w (XLOGP3) : 1.91
Log Po/w (WLOGP) : 0.88
Log Po/w (MLOGP) : -1.15
Log Po/w (SILICOS-IT) : -1.62
Consensus Log Po/w : -0.02

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.38
Solubility : 0.756 mg/ml ; 0.00415 mol/l
Class : Soluble
Log S (Ali) : -3.83
Solubility : 0.0272 mg/ml ; 0.00015 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.79
Solubility : 29.3 mg/ml ; 0.161 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 619-17-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 619-17-0 ]

* 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 [ 619-17-0 ]
  • Downstream synthetic route of [ 619-17-0 ]

[ 619-17-0 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 619-17-0 ]
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Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 2644,2646
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  • [ 619-17-0 ]
  • [ 19815-17-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
[2] Spectroscopy Letters, 2012, vol. 45, # 7, p. 530 - 540,11
[3] Patent: WO2014/120346, 2014, A1,
[4] Patent: CN103360382, 2016, B,
[5] Patent: CN103382182, 2016, B,
[6] Journal of the American Chemical Society, 2016, vol. 138, # 33, p. 10554 - 10560
[7] Patent: US2016/376298, 2016, A1,
[8] Patent: US2017/174638, 2017, A1,
  • 3
  • [ 77287-34-4 ]
  • [ 619-17-0 ]
  • [ 20872-93-9 ]
YieldReaction ConditionsOperation in experiment
86.6% at 150℃; for 16 h; 2-amino-4-nitrobenzoic acid (7.28g, 40.0mmol) and ammonium formate (3.78g, 60.0mmol) were added to 1OmL of formamide, heated to 150 ° C, incubated 16h, cooled to room temperature, Precipitation of solid,Filtered, washed with isopropanol and dried to give 6.62 g of 86 mg as a brown needles of 7-nitro-3H-quinazolin-4-one in 86.6percent yield.
83% at 140℃; General procedure: To a three necked flask, substituted anthranilic acid (1 meq.) was added in excess of formamide (6 meq). The reaction mixture was then heated at 140 °C for 4-6 h. The reaction was monitored with thin layer chromatography and upon completion; ice was added to the reaction mixture. The resultant solid was filtered, washed with water, dissolved in ethyl acetate, dried over MgSO4 and concentrated to obtain the pure desired product. Where product did not precipitate on addition of ice, the reaction mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated to obtain the desired quinazolin-4(3H)-one derivatives 1-9, 11-15, 17-21 and 23-25.The amino derivatives 10, 16 and 22 were prepared using the following general procedure:To a reaction flask, substituted nitroquinazolin-4(3H)-one derivative (0.3 g, 1.56 mmol) was added followed by addition of 6 mL ethyl acetate and SnCl2*2H2O (2.12 g, 9.42 mmol), then reaction mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and quenched with saturated sodium bicarbonate solution, followed by repeated extraction with ethyl acetate (3 .x. 50 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated to obtain the desired amino substituted quinazolin-4(3H)-one derivatives 10, 16 and 22.The substituted anthranilic acid (1 g) was dissolved in excess acetic anhydride (10 mL) and the resulting reaction mixture was stirred at room temperature for 4-7 h. The reaction was monitored for completion using thin layer chromatography. The solvent was evaporated under vacuum and the resultant residue was stirred with ammonia solution for 7 h. Upon completion, the reaction mixture was extracted with ethyl acetate (3 .x. 10 mL), the organic extracts were combined, dried over MgSO4 and evaporated to obtain compounds 26-30, 31a and 32. The 2-methyl-8-nitroquinazolin-4(3H)-one intermediate (31a) was reduced to compound 31 using the same procedure as reported in Scheme 1 for the synthesis of compounds 10, 16 and 22.
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 33, p. 10554 - 10560
[2] Patent: US2017/174638, 2017, A1, . Location in patent: Paragraph 0045
[3] Tetrahedron Letters, 2003, vol. 44, # 24, p. 4455 - 4458
[4] Patent: CN103382182, 2016, B, . Location in patent: Paragraph 0113; 0115-0117
[5] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[6] Journal of the American Chemical Society, 1908, vol. 30, p. 810
[7] Yakugaku Zasshi, 1942, vol. 62, p. 66,68; dtsch. Ref. S. 24[8] Chem.Abstr., 1951, p. 1580
[9] Patent: WO2014/120346, 2014, A1, . Location in patent: Page/Page column 33
[10] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
[11] Chemistry and Biodiversity, 2018, vol. 15, # 6,
  • 4
  • [ 3473-63-0 ]
  • [ 619-17-0 ]
  • [ 20872-93-9 ]
YieldReaction ConditionsOperation in experiment
84% at 130℃; for 18 h; A mixture of 2-amino-4-nitrobenzoic acid (10.0 g, 54.93 mmol) was refluxed at 130° C. for 18 h in methoxyethanol (50 mL) and formamidine acetate (11.43 g, 109.81 mmol).
The clear reaction mixture was cooled to room-temperature to form a yellowish precipitant.
The solvent was removed under vacuum, and the precipitant was washed several times with aqueous ammonia (0.01 M).
The solid was dried in vacuo to yield 8.9 g (84percent) of a light yellow powder. 1H NMR Data: dmso-d6-ppm (δ); 12.68 (1H), 8.37 (d, 1H), 8.33 (d, 1H), 8.26 (1H) and 8.23 (dd, 1H).
Reference: [1] Patent: US2016/376298, 2016, A1, . Location in patent: Paragraph 0220
[2] Spectroscopy Letters, 2012, vol. 45, # 7, p. 530 - 540,11
[3] Patent: CN103360382, 2016, B, . Location in patent: Paragraph 0228; 0244; 0245
  • 5
  • [ 6313-33-3 ]
  • [ 619-17-0 ]
  • [ 20872-93-9 ]
YieldReaction ConditionsOperation in experiment
44% at 200℃; for 0.5 h; Example 8Synthesis of 7-aminoquinazolin-4-one 4-Nitroanthranilic acid (10.0 g, 54.9 mmol) and formamidine hydrochloride (6.63 g, 82.4 mmol) were ground together in a mortar and pestle to produce a fine, intimate mixture. The mixture was placed in a 250 mL round-bottom flask, and spread evenly over the surface. The flask was placed in an oilbath at 200° C. The solid underwent a color change, and a distillate was seen on the side of flask, but did not really melt. After 30 min the flask was removed from the heating bath. 0.3M sodium hydroxide solution (150 mL) was added to the cooled flask, the black solid mass was broken up with a spatula, and stirred for 1 h. The solid was filtered off and washed with water. The filtrate was discarded. The black solid was suspended in dichloromethane/methanol (10:1) and filtered through a plug of silica, eluting with the same solvent until no more product came off. The material was one spot by TLC, plus black baseline material, but was poorly soluble, so a large volume of solvent was needed.The filtrate was evaporated to dryness and the solid residue triturated with a little methanol and filtered to give 7-nitroquinazoline-4-one (4.65 g, 44percent).
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 19, p. 3860 - 3873
[2] Patent: US2008/161297, 2008, A1, . Location in patent: Page/Page column 46
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 11, p. 3235 - 3239
  • 6
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Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 5, p. 616 - 620
  • 7
  • [ 619-17-0 ]
  • [ 20872-93-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
  • 8
  • [ 541-41-3 ]
  • [ 77-78-1 ]
  • [ 619-17-0 ]
  • [ 73043-80-8 ]
Reference: [1] Journal of the Indian Chemical Society, 1979, vol. 56, # 7, p. 708 - 711
  • 9
  • [ 7664-93-9 ]
  • [ 342045-62-9 ]
  • [ 610-36-6 ]
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Reference: [1] Journal of the American Chemical Society, 1909, vol. 31, p. 847
  • 10
  • [ 619-17-0 ]
  • [ 31930-18-4 ]
Reference: [1] Antimicrobial Agents and Chemotherapy, 2005, vol. 49, # 9, p. 3755 - 3761
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5080 - 5092
[4] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 3, p. 497 - 506
[5] Patent: WO2006/12374, 2006, A1, . Location in patent: Page/Page column 180-181
[6] Patent: US2003/225106, 2003, A1, . Location in patent: Page 86
[7] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
  • 11
  • [ 619-17-0 ]
  • [ 109466-84-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Patent: WO2015/6100, 2015, A1,
[3] Patent: WO2015/95795, 2015, A1,
  • 12
  • [ 121-14-2 ]
  • [ 71-43-2 ]
  • [ 92-52-4 ]
  • [ 109466-84-4 ]
  • [ 99-09-2 ]
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Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 10, p. 3306 - 3314
  • 13
  • [ 619-17-0 ]
  • [ 89459-38-1 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 24, p. 6488 - 6491
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 474 - 478
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 17, p. 3344 - 3347
[4] Acta Chemica Scandinavica (1947-1973), 1939, vol. 3, p. 13,14
[5] Tetrahedron Letters, 2004, vol. 45, # 51, p. 9475 - 9477
[6] Patent: EP468683, 1992, A1,
[7] Patent: EP1612204, 2006, A1, . Location in patent: Page/Page column 48
[8] Patent: US2016/158377, 2016, A1, . Location in patent: Paragraph 106
[9] Patent: WO2016/94509, 2016, A1, . Location in patent: Paragraph 0001171
[10] Organic Letters, 2017, vol. 19, # 7, p. 1578 - 1581
[11] Patent: WO2017/214458, 2017, A2, . Location in patent: Page/Page column 477-478
[12] Patent: WO2017/214301, 2017, A1, . Location in patent: Page/Page column 426
[13] Patent: WO2017/214462, 2017, A2, . Location in patent: Page/Page column 625
[14] Patent: WO2017/214456, 2017, A1, . Location in patent: Page/Page column 367
[15] Patent: US2017/355769, 2017, A1, . Location in patent: Paragraph 2093; 2150
  • 14
  • [ 32315-10-9 ]
  • [ 619-17-0 ]
  • [ 63480-10-4 ]
YieldReaction ConditionsOperation in experiment
91% at 70℃; for 12 h; General procedure: A 500 mL single neck round-bottomed flask equipped with a football-shaped PTFE stirring bar (16 mm × 37 mm) was chargedwith 2-amino-5-bromobenzoic acid (10.0 g, 46.3 mmol,1.0 equiv) followed by the addition of tetrahydrofuran (230 mL,0.2 molar) and solid triphosgene (13.7 g, 46.3 mmol, 1.0 equiv)resulting in a suspension. The reaction vessel was placed into afitted metal heating mantle and the neck was equipped with a24/40 Liebig condenser. The suspension was stirred (500 rpm)and the heating mantle set to 70 °C. The suspension becamehomogenous before a white solid precipitated out after about30 minutes at 70 °C. The heterogeneous reaction mixture wasaged for 12 hours then cooled to room temperature (25 °C). Theslurry was poured into a 600 mL beaker equipped with overheadmechanical stirrer (PTFE 75 mm paddle) containing250 mL of deionized water. With vigorous stirring, the mixturebecame homogenous followed by precipitation of a pale whitesolid. The solid was collected by vacuum filtration on aBüchner funnel (7.6 cm diameter) with Whatman 1 filter paper(70 mm) and air pulled through for 5 minutes. The material was transferred to a 250 mL Erlenmeyer flask equipped with cylindricalstir bar and 50 mL of methanol was added. The slurrywas stirred for 10 minutes and then collected by vacuum filtration.The filter cake was dried under vacuum (0.1 mmHg at 25 °C) for 12 hours to afford 9b as a white powder (90percent yield).
Reference: [1] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 2529 - 2536
[2] European Journal of Medicinal Chemistry, 1994, vol. 29, # 12, p. 925 - 940
[3] Patent: EP1719771, 2006, A1, . Location in patent: Page/Page column 51
[4] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 31, p. 6883 - 6889
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  • [ 63480-10-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 22, p. 7979 - 7991
[2] Patent: US2011/263559, 2011, A1, . Location in patent: Page/Page column 20
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  • [ 619-17-0 ]
  • [ 87376-25-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 3, p. 497 - 506
  • 17
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YieldReaction ConditionsOperation in experiment
91% With borane-THF In tetrahydrofuran at 0 - 30℃; for 1 h; Inert atmosphere 5.1.132
6,7-Didehydro-17-methyl-7'-nitroquinolino[2',3':6,7]morphinan-3,14β-diol (29c)
Compound 29c was prepared from compound 23c according to the procedure used to prepare compound 24a.
Yield, 83percent; a yellow oil.
IR (neat): 3365, 2919, 1607, 1530, 1348, 1238, 1051, 756 cm-1. 1H NMR (400 MHz, CDCl3) δ: 1.48-1.58 (1H, m), 2.22 (1H, dt, J = 5.6, 12.8 Hz), 2.42 (1H, dt, J = 3.2, 12.0 Hz), 2.47 (3H, s), 2.47-2.54 (1H, m), 2.92-3.06 (3H, m), 3.13 (1H, d, J = 18.0 Hz), 3.37 (1H, d, J = 18.4 Hz), 3.68 (1H, d, J = 17.2 Hz), 3.76 (1H, d, J = 17.2 Hz), 6.76 (1H, dd, J = 2.4, 8.4 Hz), 7.14 (1H, d, J = 8.4 Hz), 7.16 (1H, d, J = 2.4 Hz), 7.23 (1H, s), 7.25 (1H, d, J = 8.8 Hz), 7.44 (1H, s), 7.67 (1H, d, J = 8.8 Hz), two protons (OH) were not observed. 13C NMR (100 MHz, CDCl3) δ: 23.9, 35.9, 36.1, 39.0, 40.5, 43.1, 45.4, 61.5, 69.3, 114.7, 116.8, 118.8, 122.3, 127.8, 127.9, 129.6, 129.8, 132.9, 135.2, 139.8, 143.1, 146.6, 154.9, 161.0. HRMS (ESI) Calcd for C24H24N3O4 [M+H]+: 418.1767. Found: 418.1774.
70% With borane-THF In tetrahydrofuran at 20℃; for 12 h; To a solution of 2-amino-4-nitrobenzoic acid (1.00 g, 5.49 mmol) in THF (20 mL) at room temperature was added BH3THF (21.96 mL, 21.96 mmol) dropwise via an addition funnel. The reaction mixture was stirred at room temperature for 12h. The reaction was then cooled in an ice bath and quenched by slow addition ofmethanol (100 mL). The mixture was concentrated and the residue was transferred toa separatory funnel containing saturated aqueous NaHCO3 solution (50 mL). The aqueous layer was extracted with ether (3 x 75 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered, and concentrated. The residue was suspended in water, filtered and dried to afford (2-amino-4-nitrophenyl)methanol (650 mg, 70percent yield) as an orange solid: ‘H NMR (400MHz, DMSO-d6) ö 7.46 (d, J=2.0 Hz, 1H), 7.38 - 7.35 (m, 2H), 5.57 (s, 2H), 5.34 (t, J5.4 Hz, 1H), 4.43 (d, J5.5 Hz, 2H).
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Patent: WO2015/6100, 2015, A1, . Location in patent: Page/Page column 113
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5080 - 5092
[4] Patent: US2003/195201, 2003, A1,
[5] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 7033 - 7036
[6] Patent: WO2015/95795, 2015, A1, . Location in patent: Paragraph 0585
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  • [ 1211589-24-0 ]
Reference: [1] Patent: WO2007/138033, 2007, A1,
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