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Chemical Structure| 864293-44-7
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Product Details of [ 864293-44-7 ]

CAS No. :864293-44-7 MDL No. :MFCD11101005
Formula : C8H8BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :YSBGYQUUOKRQAT-UHFFFAOYSA-N
M.W : 246.06 Pubchem ID :45480457
Synonyms :

Calculated chemistry of [ 864293-44-7 ]

Physicochemical Properties

Num. heavy atoms : 13
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 : 52.0
TPSA : 72.55 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.98
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 1.19
Consensus Log Po/w : 1.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.82
Solubility : 0.37 mg/ml ; 0.0015 mol/l
Class : Soluble
Log S (Ali) : -3.13
Solubility : 0.183 mg/ml ; 0.000742 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.4
Solubility : 0.984 mg/ml ; 0.004 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 864293-44-7 ]

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 [ 864293-44-7 ]

* 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 [ 864293-44-7 ]
  • Downstream synthetic route of [ 864293-44-7 ]

[ 864293-44-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 864293-44-7 ]
  • [ 157893-14-6 ]
YieldReaction ConditionsOperation in experiment
62%
Stage #1: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5 h;
Stage #2: With sodium nitrite In tetrahydrofuran; water
Stage #3: With hypophosphorous acid In tetrahydrofuran; water at 20℃;
Example 31
3-Bromo-5-(methyloxy)benzoic Acid
To a solution of 2-amino-5-bromo-3-(methyloxy)benzoic acid (16.40 g, 66.65 mmol) in H2O (80 mL), was added conc. HCl (30 mL) and THF (5 mL) at 0° C.
The reaction mixture was stirred for 30 min, and then NaNO2 (14.00 g, 202.91 mmol) was cautiously added to the solution.
This solution was stirred for 2 h, and then H3PO2 (22.00 g, 333.35 mmol) was cautiously added to the solution.
The solution was kept stirring overnight at the room temperature (monitored by TLC), then filtered and rinsed with water (50 mL*2).
The resulting solid was dried to afford 3-bromo-5-(methyloxy)benzoic acid (9.60 g, 62percent).
1H NMR (400 MHz, CDCl3) δ 7.46 (t, J=1.6 Hz, 1H), 7.31 (q, J=16.8 Hz, 1H), 7.21 (t, J=16.8 Hz, 1H), 3.84 (s, 1H).
62%
Stage #1: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5 h;
Stage #2: With sodium nitrite In tetrahydrofuran; water for 2 h;
Stage #3: With hypophosphorous acid In tetrahydrofuran; water at 20℃;
Example 34
3-Bromo-5-(methyloxy)benzoic Acid
To a solution of 2-amino-5-bromo-3-(methyloxy)benzoic acid (16.40 g, 66.65 mmol) in H2O (80 mL), conc. HCl (30 mL) and THF (5 mL) were added at 0° C.
The reaction was stirred for 30 min, and then NaNO2 (14.00 g, 202.91 mmol) was cautiously added to the solution.
After the reaction mixture had stirred for 2 h, H3PO2 (22.00 g, 333.35 mmol) was cautiously added to the solution.
The reaction was kept stirring overnight at the room temperature (monitored by TLC), and filtered and rinsed with water (50 mL*2).
The formed precipitate was dried to afford 3-bromo-5-(methyloxy)benzoic acid (9.60 g, 62percent).
1H NMR (400 MHz, CDCl3): δ 7.46 (t, J=1.6 Hz, 1H), 7.31 (q, J=16.8 Hz, 1H), 7.21 (t, J=16.8 Hz, 1H), 3.84 (s, 1H).
62%
Stage #1: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5 h;
Stage #2: With sodium nitrite In tetrahydrofuran; water at 0℃; for 2 h;
Stage #3: With hypophosphorous acid In tetrahydrofuran; water at 20℃;
Example 31 3-Bromo-5-(methyloxy)benzoic acidTo a solution of 2-amino-5-bromo-3-(methyloxy)benzoic acid (16.40 g, 66.65 mmol) in H2O (80 mL), was added cone. HCl (30 mL) and THF (5 mL) at 00C. The reaction mixture was stirred for 30 min, and then NaNO2 (14.00 g, 202.91 mmol) was cautiously added to the solution. This solution was stirred for 2 h, and then H3PO2 (22.00 g, 333.35 mmol) was cautiously added to the solution. The solution was kept stirring overnight at the room temperature (monitored by TLC), then filtered and rinsed with water (50 mL x 2). The resulting solid was dried to afford 3- bromo-5-(methyloxy)benzoic acid (9.60 g, 62percent). 1H NMR (400 MHz, CDCl3) δ 7.46 (t, J=I.6 Hz, 1 H), 7.31 (q, J=16.8 Hz, 1 H), 7.21 (t, J=16.8 Hz, 1 H), 3.84 (s, 1 H).
3.2 g
Stage #1: With hydrogenchloride; sodium nitrite In tetrahydrofuran; water at 0℃; for 2 h;
Stage #2: With hypophosphorous acid In tetrahydrofuran; water at 20℃; for 16 h;
3-Bromo-5-methoxybenzoic acid
To a solution of 2-amino-5-bromo-3-methoxybenzoic acid (4 g, 16.3 mmol) in water (20 mL) at 0° C., conc. HCl (7.5 mL, 90 mmol) and THF (20 mL) were added.
The mixture was stirred for 30 min, and then NaNO2 (3.16 g, 45.8 mmol) was added.
The resulting mixture was stirred for 2 h and then hypophosphorous acid (5.1 g, 76 mmol, 50percent in H2O) was added to the reaction.
The mixture was stirred at room temperature for 16 h.
The precipitate was collected by filtration, washed with water and dried in vacuo to afford the desired product (3.2 g, 85percent yield). ESI-MS m/z: 229.2 [M-H]-.
3.2 g
Stage #1: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.5 h;
Stage #2: With sodium nitrite In tetrahydrofuran; water for 2 h;
Stage #3: With hypophosphorous acid In tetrahydrofuran; water at 20℃; for 16 h;
To a solution of 2-amino-5-bromo-3-methoxybenzoic acid (4 g, 16.3 mmol) in water (20 mL) at 0°C, conc. HC1 (7.5 mL, 90 mmol) and THF (20 mL) were added. The mixture was stirred for 30 mm, and then NaNO2 (3.16 g, 45.8 mmol) was added. The resulting mixture was stirred for 2 h and then hypophosphorous acid (5.1 g,76 mmol, 50percent in H20) was added to the reaction. The mixture was stirred at room temperature for 16 h. The precipitate was collected by filtration, washed with water and dried in vacuo to afford the desired product (3.2 g, 85percent yield). ESI-MS m/z: 229.2 [M3

Reference: [1] Patent: US2009/203677, 2009, A1, . Location in patent: Page/Page column 53
[2] Patent: US2009/197871, 2009, A1, . Location in patent: Page/Page column 53
[3] Patent: WO2009/100169, 2009, A1, . Location in patent: Page/Page column 131
[4] Patent: US2014/288045, 2014, A1, . Location in patent: Paragraph 0512
[5] Patent: WO2016/44772, 2016, A1, . Location in patent: Paragraph 303; 304
  • 2
  • [ 864293-44-7 ]
  • [ 6303-21-5 ]
  • [ 157893-14-6 ]
YieldReaction ConditionsOperation in experiment
62%
Stage #1: With hydrogenchloride In tetrahydrofuran; water at 0℃;
Stage #2: With sodium nitrite In tetrahydrofuran; water for 2 h;
Stage #3: at 20℃;
Example 31
3-Bromo-5-(methyloxy)benzoic acid
To a solution of 2-amino-5-bromo-3-(methyloxy)benzoic acid (16.40 g, 66.65 mmol) in H2O (80 mL), was added conc. HCl (30 mL) and THF (5 mL) at 0° C.
The reaction mixture was stirred for 30 min, and then NaNO2 (14.00 g, 202.91 mmol) was cautiously added to the solution.
This solution was stirred for 2 h, and then H3PO2 (22.00 g, 333.35 mmol) was cautiously added to the solution.
The solution was kept stirring overnight at the room temperature (monitored by TLC), then filtered and rinsed with water (50 mL*2).
The resulting solid was dried to afford 3-bromo-5-(methyloxy)benzoic acid (9.60 g, 62percent).
1H NMR (400 MHz, CDCl3) δ 7.46 (t, J=1.6 Hz, 1H), 7.31 (q, J=16.8 Hz, 1H), 7.21 (t, J=16.8 Hz, 1H), 3.84 (s, 1H).
Reference: [1] Patent: US2009/203657, 2009, A1, . Location in patent: Page/Page column 50
  • 3
  • [ 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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