Home Cart 0 Sign in  
X

[ CAS No. 866775-09-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 866775-09-9
Chemical Structure| 866775-09-9
Chemical Structure| 866775-09-9
Structure of 866775-09-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 866775-09-9 ]

Related Doc. of [ 866775-09-9 ]

Alternatived Products of [ 866775-09-9 ]

Product Details of [ 866775-09-9 ]

CAS No. :866775-09-9 MDL No. :MFCD11656228
Formula : C7H7BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FETASVOVQOWEBL-UHFFFAOYSA-N
M.W : 231.05 Pubchem ID :45480453
Synonyms :

Calculated chemistry of [ 866775-09-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.62
TPSA : 65.21 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) : -6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.93
Log Po/w (WLOGP) : 1.22
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : 1.17
Consensus Log Po/w : 1.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.73
Solubility : 0.434 mg/ml ; 0.00188 mol/l
Class : Soluble
Log S (Ali) : -2.92
Solubility : 0.276 mg/ml ; 0.00119 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.6
Solubility : 0.578 mg/ml ; 0.0025 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 866775-09-9 ]

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 [ 866775-09-9 ]

* 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 [ 866775-09-9 ]
  • Downstream synthetic route of [ 866775-09-9 ]

[ 866775-09-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 36052-27-4 ]
  • [ 866775-09-9 ]
YieldReaction ConditionsOperation in experiment
74% With sulfuric acid; bromine In water; acetic acid at 10 - 35℃; for 4 h; (Step 2) (1071) To a mixture of methyl 3-aminopyridine-2-carboxylate (17 g, 111.8 mmol) in a mixed solvent of water (288 mL) and 2M sulfuric acid (58 mL) was added a solution of bromine (5.76 mL, 111.8 mmol) in acetic acid (43 mL) at room temperature, and the mixture was stirred at room temperature for 4 hr. The pH of the mixture was adjusted to 6 with 2N aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate (x2), the organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; dichloromethane) to give methyl 3-amino-6-bromopyridine-2-carboxylate (19.2 g, 74percent) as a white solid. 1H- NMR(300MHz,CDCl3)δ3.94(3H,s),5.81(2H,brs),6.93(1H,d,J=8.72Hz), 7.32(1H,d,J=8.71Hz).
69%
Stage #1: With sulfuric acid; bromine; acetic acid In water
Step 2;. Preparation of 3-amino-6-bromo-pyridine-2-carboxylic acid methyl ester; Add a solution of 2 M sulfuric acid (2 mL) to a suspension of 3-amino-pyridine-2- carboxylic acid methyl ester (0.59 g, 3.88 mmol) in water (10 mL) and stir the mixture until the precipitate is dissolved. Add dropwise a solution of bromine (0.199 mL, 3.88 mmol) in acetic acid (1.5 mL). Add a solution of 2 M sodium hydroxide until pH = 6 and extract with ethyl acetate. Separate the organic layer and extract with ethyl acetate. Dry the combined organic layers over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Purify the residue using silica gel chromatography eluting with ethyl acetate/hexanes to afford the title compound (0.616 g, 69percent). H-NMR (CDCl3,300 MHz) : No. 3.90 (s, 3 H) ; 6.90 (d, J = 8.5 Hz, 1H), 7.30 (d, J= 8.5 Hz, 1H).
54% With N-Bromosuccinimide In acetonitrile at 20℃; for 2 h; A solution of methyl 3-aminopyridine-2-carboxylate (1 g, 6.57 mmol, 1.00 equiv) and N-bromosuccinimide (1.29 g, 7.25 mmol, 1.10 equiv) in acetonitrile (25 mL) was stirred at room temperature.
After being stirred for 2 h the mixture was concentrated under vacuum.
The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1) to give the title compound (0.81 g, 54percent) as a yellow solid. LC-MS (ES, m/z): 231, 233 [M+H]+.
54% With N-Bromosuccinimide In acetonitrile at 20℃; for 2 h; A solution of methyl 3-aminopyridine-2-carboxylate (1 g, 6.57 mmol, 1.00 equiv) andN-bromosuccinimide (1.29 g, 7.25 mmol, 1.10 equiv) in acetonitrile (25 mL) was stirred at room temperature. After being stirred for 2 h the mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1) to give the title compound (0.81 g, 54percent) as a yellow solid. LC-MS (ES, mlz): 231, 233 [M+H].
50% With sulfuric acid; bromine In water at 0 - 25℃; for 24 h; 4.1
Preparation of methyl 3-amino-6-bromopyridine-2-carboxylate
20 g of methyl 3-aminopyridine-2-carboxylate are suspended in 120 ml of water in a flask.
After addition of 100 ml of sulfuric acid (2 mol/l), the mixture is cooled to 0° C., 6.73 ml of bromine are added dropwise, and the mixture is stirred at 25° C. until the acid has reacted completely (HPLC check, about 24 hours).
A precipitate precipitates out of the reaction solution.
This is filtered off, dissolved in EA, washed with sodium thiosulfate solution, the organic phase is dried and purified by means of column chromatography (gradient heptane: EA 5-100percent in 30 min.), giving 15 g of methyl 3-amino-6-bromo-pyridine-2-carboxylate as red-brown solid (yield 50percent, content 98percent); MS-FAB (M+H+)=232.9; Rf (polar method): 1.518 min.

Reference: [1] Patent: EP2975031, 2016, A1, . Location in patent: Paragraph 1071
[2] Patent: WO2005/97805, 2005, A1, . Location in patent: Page/Page column 54
[3] Patent: US2015/57260, 2015, A1, . Location in patent: Paragraph 0687; 0688
[4] Patent: WO2015/25026, 2015, A1, . Location in patent: Page/Page column 164
[5] Patent: US2013/210819, 2013, A1, . Location in patent: Paragraph 0252-0253
[6] Patent: US2017/190713, 2017, A1, . Location in patent: Paragraph 0261
  • 2
  • [ 1462-86-8 ]
  • [ 866775-09-9 ]
Reference: [1] Patent: EP2975031, 2016, A1,
[2] Patent: US2017/190713, 2017, A1,
  • 3
  • [ 866775-09-9 ]
  • [ 1052708-46-9 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With methanol; lithium hydroxide; water In tetrahydrofuran for 16 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; methanol
Example 314; Synthesis of 3-amino-6-bromopicolinic acid[0251] To a solution of methyl 3 -amino-6-bromopicolinate (2.3 Ig, lO mmoles) in 2:1 THF/MeOH (51 mL) was added 1.0 M LiOH (17 mL, 17 mmoles). After stirring <n="124"/>for 16 hours, 1 N HCl (17 mL, 17 mmoles) was added and the THF/MeOH was removed in vacuo. The resulting solid was filtered, rinsed with cold H2O (4 x 20 mL) and pumped on yielding S-amino-β-bromopicolinic acid (97percent). LCMS (m/z): 216.9 (MH+); LC Rt = 1.93 min.
96% With water; lithium hydroxide In tetrahydrofuran; methanol at 10 - 35℃; for 16 h; (Step 3) (1072) To a solution of methyl 3-amino-6-bromopyridine-2-carboxylate (10 g, 43.28 mmol) in a mixed solvent of THF and methanol (2:1, v/v, 142 mL) was added 1M aqueous lithium hydroxide solution (71 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added 1N hydrochloric acid (71 mL), and the mixture was concentrated under reduced pressure. The precipitate was collected by filtration, and the crude crystals were washed with water to give to 3-amino-6-bromopyridine-2-carboxylic acid (9.0 g, 96percent) as a grayish white solid. 1H-NMR(400MHz,DMSO-d6):δ6.50-7.05(1H,brs),7.18(1H,d,J=8.76Hz),7.42(1H,d,J=8.76Hz),11.20-13.80(1H,brs). (the peak of CO2H was not observed)
Reference: [1] Patent: WO2008/106692, 2008, A1, . Location in patent: Page/Page column 122-123
[2] Patent: EP2975031, 2016, A1, . Location in patent: Paragraph 1072
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 866775-09-9 ]

Bromides

Chemical Structure| 21190-88-5

[ 21190-88-5 ]

Ethyl 6-bromopyridine-2-carboxylate

Similarity: 0.87

Chemical Structure| 1209093-48-0

[ 1209093-48-0 ]

Methyl 6-bromo-5-methylpicolinate

Similarity: 0.85

Chemical Structure| 797060-52-7

[ 797060-52-7 ]

Methyl 5-amino-6-bromopicolinate

Similarity: 0.84

Chemical Structure| 1206248-47-6

[ 1206248-47-6 ]

Methyl 4,6-dibromopicolinate

Similarity: 0.83

Chemical Structure| 1807149-82-1

[ 1807149-82-1 ]

Ethyl 6-bromo-5-methylpicolinate

Similarity: 0.83

Esters

Chemical Structure| 21190-88-5

[ 21190-88-5 ]

Ethyl 6-bromopyridine-2-carboxylate

Similarity: 0.87

Chemical Structure| 36052-27-4

[ 36052-27-4 ]

Methyl 3-aminopicolinate

Similarity: 0.87

Chemical Structure| 1209093-48-0

[ 1209093-48-0 ]

Methyl 6-bromo-5-methylpicolinate

Similarity: 0.85

Chemical Structure| 27507-15-9

[ 27507-15-9 ]

Ethyl 3-aminopicolinate

Similarity: 0.85

Chemical Structure| 797060-52-7

[ 797060-52-7 ]

Methyl 5-amino-6-bromopicolinate

Similarity: 0.84

Amines

Chemical Structure| 36052-27-4

[ 36052-27-4 ]

Methyl 3-aminopicolinate

Similarity: 0.87

Chemical Structure| 27507-15-9

[ 27507-15-9 ]

Ethyl 3-aminopicolinate

Similarity: 0.85

Chemical Structure| 797060-52-7

[ 797060-52-7 ]

Methyl 5-amino-6-bromopicolinate

Similarity: 0.84

Chemical Structure| 1072448-08-8

[ 1072448-08-8 ]

Methyl 3-amino-5-bromopicolinate

Similarity: 0.80

Chemical Structure| 1462-86-8

[ 1462-86-8 ]

3-Aminopicolinic acid

Similarity: 0.80

Related Parent Nucleus of
[ 866775-09-9 ]

Pyridines

Chemical Structure| 21190-88-5

[ 21190-88-5 ]

Ethyl 6-bromopyridine-2-carboxylate

Similarity: 0.87

Chemical Structure| 36052-27-4

[ 36052-27-4 ]

Methyl 3-aminopicolinate

Similarity: 0.87

Chemical Structure| 1209093-48-0

[ 1209093-48-0 ]

Methyl 6-bromo-5-methylpicolinate

Similarity: 0.85

Chemical Structure| 27507-15-9

[ 27507-15-9 ]

Ethyl 3-aminopicolinate

Similarity: 0.85

Chemical Structure| 797060-52-7

[ 797060-52-7 ]

Methyl 5-amino-6-bromopicolinate

Similarity: 0.84