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[ CAS No. 606-18-8 ] {[proInfo.proName]}

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Chemical Structure| 606-18-8
Chemical Structure| 606-18-8
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Product Details of [ 606-18-8 ]

CAS No. :606-18-8 MDL No. :MFCD00024261
Formula : C7H6N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :JJPIVRWTAGQTPQ-UHFFFAOYSA-N
M.W : 182.13 Pubchem ID :219633
Synonyms :

Calculated chemistry of [ 606-18-8 ]      Expand+

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) : -6.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.81
Log Po/w (XLOGP3) : 1.09
Log Po/w (WLOGP) : 0.88
Log Po/w (MLOGP) : -1.15
Log Po/w (SILICOS-IT) : -1.62
Consensus Log Po/w : 0.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.87
Solubility : 2.48 mg/ml ; 0.0136 mol/l
Class : Very soluble
Log S (Ali) : -2.97
Solubility : 0.193 mg/ml ; 0.00106 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 : 1.82

Safety of [ 606-18-8 ]

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

Application In Synthesis of [ 606-18-8 ]

* 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 [ 606-18-8 ]
  • Downstream synthetic route of [ 606-18-8 ]

[ 606-18-8 ] Synthesis Path-Upstream   1~16

  • 1
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  • [ 46006-36-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
[3] Patent: WO2018/42362, 2018, A1,
  • 2
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  • [ 6924-71-6 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
  • 3
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  • [ 3970-35-2 ]
Reference: [1] Patent: US2005/20626, 2005, A1, . Location in patent: Page 17-18
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  • [ 603-81-6 ]
YieldReaction ConditionsOperation in experiment
69% With palladium 10% on activated carbon; hydrogen In methanol 2-amino-3-nitrobenzoic acid (9.36 g, 51.4 mmol) was dissolved in MeOH (100 mL) and there was added 10percent Pd/C (2.0g). The reaction was stirred under H2-atmosphere (ambient pressure) until absorption ceased. The reaction was filtered through a pad of Celite and the filtrate was evaporated under reduced pressure. The product was purified by flash chromatography (CH2Cl2/MeOH 5:1) and the collected fractions were evaporated to give the title compound (5.40 g, 69percent) as a dark brown solid. mp. 199 °C dec. (Litt4. 201 °C dec.). 1H NMR (300 MHz, DMSO-d6) δ 7.09 (dd, J = 8.0, 1.5 Hz, 1H), 6.67 (dd, J = 7.4, 1.5 Hz, 1H), 6.34 (dd, J = 8.0, 7.4 Hz, 2H), 6.32 (br s, 4H). 13C NMR (75 MHz, DMSO-d6) δ 170.5, 139.6, 135.6, 119.4, 117.0, 114.9, 110.3
1.5 g With palladium on activated charcoal; hydrogen In methanol at 25℃; for 15 h; To a solution of 2-amino-3-nitrobenzoic acid (2.0g, 0.01092 mole) in methanol (30 mL) at 25 °C, was added Pd/C (2.0 g) and stirred for 15 hours under H2 gas atmosphere. Reaction mixture was filtered through celite, washed with methanol (50 mL) and filtrate was concentrated under vacuum to obtain 2,3-diaminobenzoic acid. Yield: 1.5 g; lH - NMR (DMSO- , 400 MHz) δ ppm: 4.92 - 5.22 (m, 4H),6.34 - 6.35 (t, J = 7.6 Hz, 1H), 6.66 - 6.68 (d,J = 7.3 Hz, 1H), 7.08-7.10 (d, J = 7.9 Hz, 1H), 8.12 (m, lH); Mass (m/z): 153.2 (M+H)+.
Reference: [1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 23, p. 4342 - 4350
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
[4] Patent: US6100283, 2000, A,
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 2, p. 814 - 819
[6] Journal of Medicinal Chemistry, 1992, vol. 35, # 24, p. 4595 - 4601
[7] Journal of Medicinal Chemistry, 1996, vol. 39, # 24, p. 4692 - 4703
[8] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 2, p. 267 - 269
[9] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 8, p. 2641 - 2649
[10] Patent: US2011/269766, 2011, A1,
[11] Patent: WO2018/42362, 2018, A1, . Location in patent: Page/Page column 50
[12] Patent: US6358978, 2002, B1,
  • 5
  • [ 607-35-2 ]
  • [ 64-19-7 ]
  • [ 25369-31-7 ]
  • [ 606-18-8 ]
  • [ 97271-98-2 ]
  • [ 97272-30-5 ]
  • [ 97271-96-0 ]
  • [ 97271-97-1 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 3, p. 511 - 518
  • 6
  • [ 606-18-8 ]
  • [ 5398-69-6 ]
Reference: [1] Journal of the Chemical Society, 1920, vol. 117, p. 775
  • 7
  • [ 67-56-1 ]
  • [ 606-18-8 ]
  • [ 57113-91-4 ]
YieldReaction ConditionsOperation in experiment
68% With thionyl chloride In methanol at 0℃; for 23 h; Heating / reflux (3)
methyl 3-nitroanthranilate
thionyl chloride (14.6 ML, 200 mmol) was dropwise added to methanol (150 ML) under cooling with ice..
The resulting solution was added 3-nitroanthranilic acid (3.65 g, 20 mmol), heated under reflux for 23 hours, and then placed under reduced pressure to distill the solvent off..
To the residue were added toluene and aqueous saturated sodium hydrogen carbonate..
The organic portion was taken out, dried over anhydrous magnesium sulfate, and placed under reduced pressure to distill the solvent off.
There was obtained 2.68 g (yield 68) of the desired compound in the form of a yellow crystalline product. 1H NMR (CDCl3, 500 MHz) δ: 3.92 (3H, s), 6.66 (1H, dd, J=8Hz, 8Hz), 8.24 (1H, dd, J=2Hz, 8Hz), 8.38 (1H, dd, J=2Hz, 8Hz).
61% for 48 h; Heating / reflux After dissolving 2-amino-3-nitrobenzoic acid (1.00 g, 5.49 mmol) in methanol (40 ml), sulfuric acid (0.50 ml) was added and the mixture was heated to reflux for 2 days. The reaction mixture was cooled to room temperature, and then the pH was adjusted to approximately 9 with saturated aqueous sodium bicarbonate and the mixture was concentrated under reduced pressure to approximately 10 ml. Water (20 ml) was added, the mixture was extracted with ethyl acetate (10 ml x 3 times), and the obtained organic layer was dried over anhydrous magnesium sulfate. It was then concentrated under reduced pressure, and the produced crystals were dried to obtain 2-amino-3-nitrobenzoic acid methyl ester. The compound was identified by NMR. Yield: 661.4 mg (61percent).1H-NMR (270 MHz, CDCl3): δ8.50(br), 8.37(1H,dd,J=8.6,1.4 Hz), 8.23(1H,dd,J=7.6,1.4 Hz), 6.65(1H,dd,J=8.6,7.6Hz), 3.92(3H,s) ppm.
Reference: [1] Patent: EP1452528, 2004, A1, . Location in patent: Page 21-22
[2] Patent: EP1502916, 2005, A1, . Location in patent: Page 435
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
[4] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
[5] Patent: WO2007/100295, 2007, A1, . Location in patent: Page/Page column 253
[6] Chinese Chemical Letters, 2017, vol. 28, # 4, p. 919 - 926
  • 8
  • [ 606-18-8 ]
  • [ 77-78-1 ]
  • [ 57113-91-4 ]
YieldReaction ConditionsOperation in experiment
83.8%
Stage #1: at 20℃; for 1 h;
Stage #2: for 24 h; Reflux
(III) LiOH (7.6 g) was added to a solution of the product just obtained in stage (II) (30 g) in THF (450 ml) and the mixture was stirred at room temperature for 1 h. Dimethyl sulfate (17.25 ml) was then added and the mixture was heated under reflux for 24 h. The reaction mixture was cooled to room temperature and filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the solution was washed with NH4OH solution, water and sat. NaCI solution. The organic phase was dried over anhydrous Na2SO4 and concentrated to obtain the desired product. Yield: 83.8 percent
Reference: [1] Patent: WO2010/142402, 2010, A1, . Location in patent: Page/Page column 109-110
  • 9
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  • [ 57113-91-4 ]
Reference: [1] Patent: US6100283, 2000, A,
  • 10
  • [ 606-18-8 ]
  • [ 18107-18-1 ]
  • [ 57113-91-4 ]
Reference: [1] Patent: WO2007/51062, 2007, A2, . Location in patent: Page/Page column 132
  • 11
  • [ 186581-53-3 ]
  • [ 606-18-8 ]
  • [ 57113-91-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 119 - 124
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 6106 - 6119
[3] Patent: WO2010/115736, 2010, A2, . Location in patent: Page/Page column 62
  • 12
  • [ 607-35-2 ]
  • [ 64-19-7 ]
  • [ 25369-31-7 ]
  • [ 606-18-8 ]
  • [ 97271-98-2 ]
  • [ 97272-30-5 ]
  • [ 97271-96-0 ]
  • [ 97271-97-1 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 3, p. 511 - 518
  • 13
  • [ 606-18-8 ]
  • [ 107582-20-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 6106 - 6119
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 119 - 124
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
[4] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
[5] Chinese Chemical Letters, 2017, vol. 28, # 4, p. 919 - 926
[6] Patent: EP1452528, 2004, A1,
  • 14
  • [ 606-18-8 ]
  • [ 37619-25-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
  • 15
  • [ 606-18-8 ]
  • [ 78146-52-8 ]
  • [ 162135-93-5 ]
Reference: [1] Patent: US5545646, 1996, A,
  • 16
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  • [ 711007-44-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
[2] Patent: US2011/218103, 2011, A1,
[3] Patent: EP2561759, 2013, A1,
[4] Organic Process Research and Development, 2007, vol. 11, # 4, p. 693 - 698
[5] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 1135 - 1146
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