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Chemical Structure| 3177-80-8
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Product Details of [ 3177-80-8 ]

CAS No. :3177-80-8 MDL No. :MFCD00075178
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :SXOPCLUOUFQBJV-UHFFFAOYSA-N
M.W : 167.16 Pubchem ID :255720
Synonyms :

Calculated chemistry of [ 3177-80-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 44.3
TPSA : 72.55 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) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.8
Log Po/w (XLOGP3) : 1.61
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : -0.37
Log Po/w (SILICOS-IT) : 0.5
Consensus Log Po/w : 0.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.24 mg/ml ; 0.00744 mol/l
Class : Soluble
Log S (Ali) : -2.75
Solubility : 0.3 mg/ml ; 0.0018 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.53
Solubility : 4.91 mg/ml ; 0.0294 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.31

Safety of [ 3177-80-8 ]

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 [ 3177-80-8 ]

* 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 [ 3177-80-8 ]
  • Downstream synthetic route of [ 3177-80-8 ]

[ 3177-80-8 ] Synthesis Path-Upstream   1~34

  • 1
  • [ 3177-80-8 ]
  • [ 77287-34-4 ]
  • [ 16064-27-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2794 - 2809
[2] Journal of Medicinal Chemistry, 1983, vol. 26, # 3, p. 420 - 425
[3] Journal of Scientific and Industrial Research, 1956, vol. 15 C, p. 1,2
  • 2
  • [ 3177-80-8 ]
  • [ 16064-27-0 ]
  • [ 90915-46-1 ]
  • [ 104510-25-0 ]
  • [ 1332493-37-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 17, p. 6089 - 6099
  • 3
  • [ 3177-80-8 ]
  • [ 16064-27-0 ]
Reference: [1] Patent: WO2004/31161, 2004, A1, . Location in patent: Page 117
  • 4
  • [ 3177-80-8 ]
  • [ 61948-60-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 10, p. 2297 - 2300
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 14, p. 2763 - 2773
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156
[4] Patent: WO2014/101113, 2014, A1,
[5] Patent: WO2014/101120, 2014, A1,
[6] Patent: WO2014/105666, 2014, A1,
[7] Patent: WO2014/101373, 2014, A1,
[8] Patent: WO2014/105664, 2014, A1,
[9] Patent: US2016/90374, 2016, A1,
[10] Patent: EP322133, 1989, A1,
  • 5
  • [ 3177-80-8 ]
  • [ 607-68-1 ]
  • [ 61948-60-5 ]
Reference: [1] Patent: US5686458, 1997, A,
  • 6
  • [ 3177-80-8 ]
  • [ 20197-99-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 10, p. 2297 - 2300
  • 7
  • [ 3177-80-8 ]
  • [ 548-93-6 ]
Reference: [1] Biochemical Preparations, 1958, vol. 6, p. 20,21
[2] Journal of the American Chemical Society, 1948, vol. 70, p. 1847
  • 8
  • [ 4920-80-3 ]
  • [ 3177-80-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 14, p. 2763 - 2773
[2] Journal of Medicinal Chemistry, 1984, vol. 27, # 3, p. 363 - 367
[3] Patent: EP322133, 1991, B1,
[4] Patent: EP322133, 1989, A1,
[5] Chemistry - A European Journal, 2008, vol. 14, # 36, p. 11610 - 11622
[6] Journal of the American Chemical Society, 1933, vol. 55, p. 706,712
[7] Journal of the American Chemical Society, 1948, vol. 70, p. 1847
[8] Biochemical Preparations, 1958, vol. 6, p. 20,21
[9] Helvetica Chimica Acta, 1924, vol. 7, p. 698
[10] Chemische Berichte, 1956, vol. 89, p. 2174,2178
[11] Journal of the Chemical Society, 1912, vol. 101, p. 548
[12] Justus Liebigs Annalen der Chemie, 1912, vol. 391, p. 44
[13] Journal of the American Chemical Society, 1933, vol. 55, p. 4234,4236
[14] Australian Journal of Chemistry, 1976, vol. 29, p. 2003 - 2021
[15] Journal of Organic Chemistry, 1967, vol. 32, p. 62 - 66
[16] Chemistry of Natural Compounds, 1986, vol. 22, # 4, p. 435 - 438[17] Khimiya Prirodnykh Soedinenii, 1986, vol. 22, # 4, p. 465 - 469
[18] Patent: US5064833, 1991, A,
[19] Patent: US4347246, 1982, A,
[20] Patent: US4440941, 1984, A,
[21] Letters in Drug Design and Discovery, 2013, vol. 10, # 4, p. 369 - 373
  • 9
  • [ 5345-42-6 ]
  • [ 3177-80-8 ]
Reference: [1] Chemistry of Natural Compounds, 1986, vol. 22, # 4, p. 435 - 438[2] Khimiya Prirodnykh Soedinenii, 1986, vol. 22, # 4, p. 465 - 469
[3] Biochemical Preparations, 1958, vol. 6, p. 20,21
[4] Australian Journal of Chemistry, 1976, vol. 29, p. 2003 - 2021
[5] Letters in Drug Design and Discovery, 2013, vol. 10, # 4, p. 369 - 373
  • 10
  • [ 34954-65-9 ]
  • [ 3177-80-8 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 20, p. 6797 - 6801
  • 11
  • [ 4920-77-8 ]
  • [ 3177-80-8 ]
Reference: [1] Australian Journal of Chemistry, 1976, vol. 29, p. 2003 - 2021
[2] Letters in Drug Design and Discovery, 2013, vol. 10, # 4, p. 369 - 373
  • 12
  • [ 115378-20-6 ]
  • [ 3177-80-8 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1987, # 20, p. 1528 - 1530
[2] Tetrahedron Letters, 2011, vol. 52, # 17, p. 2262 - 2264
  • 13
  • [ 90-04-0 ]
  • [ 3177-80-8 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1987, # 20, p. 1528 - 1530
[2] Bulletin de la Societe Chimique de France, 1950, p. 782,785
[3] Tetrahedron Letters, 2011, vol. 52, # 17, p. 2262 - 2264
  • 14
  • [ 84575-27-9 ]
  • [ 3177-80-8 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 602 - 604
  • 15
  • [ 33768-49-9 ]
  • [ 3177-80-8 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1987, # 20, p. 1528 - 1530
[2] Tetrahedron Letters, 2011, vol. 52, # 17, p. 2262 - 2264
  • 16
  • [ 108-39-4 ]
  • [ 3177-80-8 ]
Reference: [1] Letters in Drug Design and Discovery, 2013, vol. 10, # 4, p. 369 - 373
  • 17
  • [ 63478-14-8 ]
  • [ 3177-80-8 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 50, p. 6111 - 6114
[2] Tetrahedron, 1991, vol. 47, # 27, p. 5051 - 5070
  • 18
  • [ 73453-77-7 ]
  • [ 3177-80-8 ]
Reference: [1] Tetrahedron, 1991, vol. 47, # 27, p. 5051 - 5070
[2] Tetrahedron Letters, 1986, vol. 27, # 50, p. 6111 - 6114
  • 19
  • [ 857193-93-2 ]
  • [ 3177-80-8 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1950, p. 782,785
  • 20
  • [ 99-06-9 ]
  • [ 3177-80-8 ]
Reference: [1] Journal of the Chemical Society, 1912, vol. 101, p. 548
  • 21
  • [ 586-38-9 ]
  • [ 3177-80-8 ]
Reference: [1] Journal of the Chemical Society, 1912, vol. 101, p. 548
  • 22
  • [ 66354-88-9 ]
  • [ 3177-80-8 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1950, p. 782,785
  • 23
  • [ 3177-80-8 ]
  • [ 5121-34-6 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With potassium hydroxide In diethyl ether; water at 0℃;
Step A:; To a 60 mL of aqueous solution of KOH (2.68 g, 47.8 mmol) was added ether (200 mL) followed by the addition of 1-methyl-3-nitro-1-nitrosoguanidine (5.28 g, 35.9 mmol) slowly at 0° C. The ethereal layer was isolated and added into a solution of 2-amino-3-methoxybenzoic acid (2.0 g, 11.9 mmol) in acetone (20 mL). The reaction mixture was quenched with 2 mL of acetic acid and concentrated under reduced pressure. The residue was dissolved into ether and washed with saturated solution of NaHCO3, brine, dried over Na2SO4, filtered and concentrated to a light orange solid (2.16 g, 99percent): 1H NMR (300 MHz, CDCl3) δ 7.47 (dd, J=8.2, 1.0 Hz, 1H), 6.85 (dd, J=7.8, 1.2 Hz, 1H), 6.58 (t, J=8.4 Hz, 1H), 6.00 (br s, 2H), 3.87 (s, 6H).
Reference: [1] Patent: US2006/183769, 2006, A1, . Location in patent: Page/Page column 36
[2] Journal of Physical Chemistry A, 2012, vol. 116, # 22, p. 5325 - 5336
  • 24
  • [ 67-56-1 ]
  • [ 3177-80-8 ]
  • [ 5121-34-6 ]
YieldReaction ConditionsOperation in experiment
91% at 95℃; (c) methyl 2-amino-3-methoxybenzoate To a solution of 2-amino-3-methoxybenzoic acid (34.5 g, 206 mmol) in MeOH (250 mL) was added concentrated H2SO4 (50 mL) slowly. The reaction mixture was heated at 95 °C overnight. The reaction mixture was cooled to room temperature, and concentrated in vacuo. The residue was a beige slurry which was mixed with Et20 and poured slowly into a mixture of Et20 and cold aqueous saturated Na2C03 containing excess Na2C03. The Et20 layer was separated and aqueous layer was extracted with Et20 two more times. The combined Et20 extracts were washed with diluted NaOH (2x), brine and dried over Na2S04, filtered through a short silica plug and concentrated in vacuo to afford methyl 2-amino-3-methoxybenzoate (34.0 g, 91percent) as a tan solid. LC-MS(ES) m/z = 182 [M+H]+.
Reference: [1] Patent: WO2014/195919, 2014, A1, . Location in patent: Page/Page column 68
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 602 - 604
[3] Patent: WO2007/30582, 2007, A2, . Location in patent: Page/Page column 95
  • 25
  • [ 3177-80-8 ]
  • [ 80-11-5 ]
  • [ 5121-34-6 ]
Reference: [1] Heterocycles, 2006, vol. 67, # 1, p. 161 - 173
  • 26
  • [ 186581-53-3 ]
  • [ 3177-80-8 ]
  • [ 5121-34-6 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1987, # 20, p. 1528 - 1530
[2] Tetrahedron Letters, 2011, vol. 52, # 17, p. 2262 - 2264
  • 27
  • [ 3177-80-8 ]
  • [ 70127-96-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6474 - 6477
  • 28
  • [ 3177-80-8 ]
  • [ 10541-78-3 ]
Reference: [1] Journal of the Chemical Society, 1912, vol. 101, p. 548
  • 29
  • [ 3177-80-8 ]
  • [ 157893-14-6 ]
Reference: [1] Patent: US2014/288045, 2014, A1,
[2] Patent: WO2016/44772, 2016, A1,
[3] Patent: WO2009/100169, 2009, A1,
  • 30
  • [ 3177-80-8 ]
  • [ 88377-29-1 ]
YieldReaction ConditionsOperation in experiment
74% With hydrogen bromide; copper(I) bromide; sodium nitrite In water at 0 - 60℃; for 2 h; REAGENT PREPARATION 20: 2-bromo-3-(methyloxy)benzoic acid:[00932] To 2-amino-3-(methyloxy)benzoic acid (4.00 g, 23.9 mmol) in 10percent aqueous hydrobromic acid (54 ml) at O0C was added sodium nitrite (1.65 g, 23.9 mmol) in water (17 ml). To this solution was added dropwise a solution of copper (I) <n="391"/>bromide (3.78 g, 26.3 mmol) in 48percent hydrobromic acid (22 ml) and heated to 6O0C for 2 h. The mixture was cooled to O0C, and the resultant precipitate was collected by filtration, washed with cold water and recrystallized from water to give pure 2-bromo- 3-(methyloxy)benzoic acid (4.07g, 74percent). MS (EI) for C8H7BrO3: 232 (MH+).
Reference: [1] Tetrahedron, 2001, vol. 57, # 23, p. 4967 - 4975
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 40, p. 7257 - 7260
[3] Patent: WO2009/55077, 2009, A1, . Location in patent: Page/Page column 388-389
[4] Journal of Medicinal Chemistry, 1984, vol. 27, # 3, p. 363 - 367
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3018 - 3022
[6] Justus Liebigs Annalen der Chemie, 1912, vol. 391, p. 44
[7] Justus Liebigs Annalen der Chemie, 1935, vol. 516, p. 248,262
  • 31
  • [ 3177-80-8 ]
  • [ 88377-31-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 3, p. 363 - 367
  • 32
  • [ 3177-80-8 ]
  • [ 205877-13-0 ]
YieldReaction ConditionsOperation in experiment
100% With borane-THF In tetrahydrofuran at 0 - 20℃; for 1.66667 h; Inert atmosphere General procedure: To a solution of 6-chloroanthranilic acid (1.5 g, 8.74 mmol) in THF (5 mL) was added dropwise 1.08 M borane–tetrahydrofuran complex in THF (24.3 mL, 26.2 mmol) at 0 °C under an Ar atmosphere for 10 min. After 1.5 h with stirring at 30 °C, the solution was cooled at 0 °C, added aqueous THF (THF/H2O = 1:1, 60 mL) and potassium carbonate, and extracted with diethyl ether three times. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was crystallized from AcOEt to give 1a (1.2 g, 88percent) as a white needle crystal.
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 7, p. 1193 - 1202
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 2080 - 2092
[4] Journal of Medicinal Chemistry, 2002, vol. 45, # 15, p. 3280 - 3285
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 49, p. 15272 - 15276[6] Angew. Chem., 2016, vol. 128, # 49, p. 15498 - 15502,5
[7] Canadian Journal of Chemistry, 2016, vol. 94, # 4, p. 305 - 311
[8] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6474 - 6477
  • 33
  • [ 3177-80-8 ]
  • [ 214476-78-5 ]
Reference: [1] Patent: EP973746, 2003, B1,
  • 34
  • [ 3177-80-8 ]
  • [ 864293-44-7 ]
YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide In methanol at -5 - 0℃; Example 30
2-Amino-5-bromo-3-(methyloxy)benzoic acid
To a solution of 2-amino-3-(methyloxy)benzoic acid (15.0 g, 89.7 mmol) in MeOH (100 mL) was added NBS (16.8 g, 94.2 mmol) at -5° C.
The reaction was kept stirring at 0° C. overnight, then put into the ice water under the condition of stirring.
A precipitate formed and was filtered out using Celite, and dried in vacuo to afford 2-amino-5-bromo-3-(methyloxy)benzoic acid (22.0 g, 99percent).
1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 6.93 (s, 1H), 3.87 (s, 3H).
99% With N-Bromosuccinimide In methanol at -5 - 0℃; Example 30
2-Amino-5-bromo-3-(methyloxy)benzoic Acid
To a solution of 2-amino-3-(methyloxy)benzoic acid (15.0 g, 89.7 mmol) in MeOH (100 mL) was added NBS (16.8 g, 94.2 mmol) at -5° C.
The reaction was kept stirring at 0° C. overnight, then put into the ice water under the condition of stirring.
A precipitate formed and was filtered out using Celite, and dried in vacuo to afford 2-amino-5-bromo-3-(methyloxy)benzoic acid (22.0 g, 99percent).
1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 6.93 (s, 1H), 3.87 (s, 3H).
99% With N-Bromosuccinimide In methanol at -5 - 0℃; Example 33
2-Amino-5-bromo-3-(methyloxy)benzoic Acid
To a solution of 2-amino-3-(methyloxy)benzoic acid (15.0 g, 89.7 mmol) in MeOH (100 mL), NBS (16.8 g, 94.2 mmol) was added at -5° C.
The reaction was kept stirring at 0° C. overnight, then put into the ice water under the condition of stirring.
A precipitate formed and was filtered over Celite and dried in vacuo to afford 2-amino-5-bromo-3-(methyloxy)benzoic acid (22.0 g, 99percent).
1H NMR (400 MHz, CDCl3): δ 7.65 (s, 1H), 6.93 (s, 1H), 3.87 (s, 3H).
99% With N-Bromosuccinimide In methanol at -5 - 0℃; Example 30 2-Amino-5-bromo-3-(methyloxy)benzoic acidTo a solution of 2-amino-3-(methyloxy)benzoic acid (15.0 g, 89.7 mmol) in MeOH(100 mL) was added NBS (16.8 g, 94.2 mmol) at -5 0C. The reaction was kept stirring at 00C overnight, then put into the ice water under the condition of stirring. A precipitate formed and was filtered out using Celite, and dried in vacuo to afford 2-amino-5-bromo-3-(methyloxy) benzoic acid (22.0 g, 99percent). 1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1 H), 6.93 (s, 1 H), 3.87 (s, 3 H).
82.2% With N-Bromosuccinimide In dichloromethane at 20℃; for 2 h; To a solution of 2-amino-3-methoxybenzoic acid (10.0 g, 59.8 mmol,1.0 eq) in DCM (150 mL) was added NBS (10.6 g, 59.8 mmol, 1.0 eq) and the mixture was stirred at rt for 2 h. The solid was filtered and washed with DCM (lOOmL x 2) to provide 2-amino-5-bromo-3-methoxybenzoic acid as a grey solid (12.1 g, 82.2percent).

Reference: [1] Patent: US2009/203657, 2009, A1, . Location in patent: Page/Page column 50
[2] Patent: US2009/203677, 2009, A1, . Location in patent: Page/Page column 53
[3] Patent: US2009/197871, 2009, A1, . Location in patent: Page/Page column 52-53
[4] Patent: WO2009/100169, 2009, A1, . Location in patent: Page/Page column 131
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6087 - 6109
[6] Patent: WO2018/35061, 2018, A1, . Location in patent: Paragraph 0288; 0411
[7] Patent: WO2010/7116, 2010, A2, . Location in patent: Page/Page column 78
[8] Patent: WO2010/7114, 2010, A2, . Location in patent: Page/Page column 112
[9] Patent: US2014/288045, 2014, A1, . Location in patent: Paragraph 0511
[10] Journal of Medicinal Chemistry, 2015, vol. 58, # 8, p. 3548 - 3571
[11] Patent: WO2016/44772, 2016, A1, . Location in patent: Paragraph 303; 304
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