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[ CAS No. 1211533-83-3 ] {[proInfo.proName]}

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Chemical Structure| 1211533-83-3
Chemical Structure| 1211533-83-3
Structure of 1211533-83-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1211533-83-3 ]

CAS No. :1211533-83-3 MDL No. :MFCD08062947
Formula : C6H7BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :STTFWVSVDMLUCF-UHFFFAOYSA-N
M.W : 203.04 Pubchem ID :53420205
Synonyms :

Calculated chemistry of [ 1211533-83-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.83
TPSA : 48.14 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) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 1.5
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 1.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.42
Solubility : 0.769 mg/ml ; 0.00379 mol/l
Class : Soluble
Log S (Ali) : -2.12
Solubility : 1.54 mg/ml ; 0.00761 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.65
Solubility : 0.453 mg/ml ; 0.00223 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 1211533-83-3 ]

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 [ 1211533-83-3 ]

* 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 [ 1211533-83-3 ]
  • Downstream synthetic route of [ 1211533-83-3 ]

[ 1211533-83-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 67-56-1 ]
  • [ 89284-11-7 ]
  • [ 1211533-83-3 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: at -20 - 0℃; for 4 h;
Stage #2: at 120℃; for 24 h; Sealed tube
Stage #3: With water In methanol
Example 7b
5-Bromo-6-methoxy-pyridin-2-ylamine
Sodium metal (1.8 g, 78.2 mmol) was added to dry MeOH (70 mL) at -20° C. in small portions.
The solution was stirred for 4 h at 0° C. and added to a pressure vessel containing 5,6-dibromo-pyridin-2-ylamine (Example 7a, 10 g, 39.8 mmol).
The reaction mixture was heated in a sealed tube at 120° C. for 24 h.
The solvent was removed under reduced pressure and the residue was diluted with water.
The aqueous phase was neutralized using 2 M HCl and extracted with EtOAc (3*100 mL).
The combined extracts were dried over MgSO4, filtered and concentrated in vacuo.
The residue was purified by flash column chromatography using a gradient of 5 to 15percent acetone in hexane to afford the title compound (6.6 g, 82percent).
1H NMR (400 MHz, CDCl3) δ ppm 3.91 (s, 3H), 4.31 (br. s., 2 H), 5.99 (d, 1H), 7.48 (d, 1H). ESMS m/z 202.8, 204.8 [M+H]+.
72%
Stage #1: at -20 - 0℃; for 4 h; Inert atmosphere
Stage #2: at 120℃; for 24 h; Inert atmosphere
A mixture of sodium metal (1.1 g, 47.80 mmol) in MeOH (45 mL) under an argon atmosphere was stirred at -20 oC to 0 oC for 4 h. The reaction mixture was stirred at 120 oC for 24 h. After consumption of the starting material (monitored by TLC), the volatile components were evaporated in vacuo. The residue was diluted with water (100 mL), neutralized with a 2 M HCl solution (20 mL) and extracted with EtOAc (2 x 200 mL). The combined organic extracts were dried were sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 10percent EtOAc:hexanes to afford 5-bromo-6-methoxypyridin-2-amine (3.5 g, 72percent) as an off-white solid. 1H-NMR (CD3OD, 400 MHz): δ 7.48 (d, 1H), 5.98 (d, 1H), 4.30 (s, 2H), 3.90 (s, 3H); LCMS: 205.2 (M+2); (column; X-Select CSH C-18 (50 × 3.0 mm, 3.5 µm); RT 3.52 min 0.05percent Aq TFA: ACN; 0.80 mL/min); TLC: 30percent EtOAc:hexanes (Rf: 0.5).
72% at 120℃; for 24 h; Inert atmosphere Synthesis of 5-bromo-6-methoxypyridin-2-amine
A mixture of sodium metal (1.1 g, 47.80 mmol) in MeOH (45 mL) under an argon atmosphere was stirred at -20° C. to 0° C. for 4 h.
The reaction mixture was stirred at 120° C. for 24 h.
After consumption of the starting material (monitored by TLC), the volatile components were evaporated in vacuo.
The residue was diluted with water (100 mL), neutralized with a 2 M HCl solution (20 mL) and extracted with EtOAc (2*200 mL).
The combined organic extracts were dried were sodium sulfate, filtered and concentrated in vacuo.
The crude material was purified by column chromatography using 10percent EtOAc:hexanes to afford 5-bromo-6-methoxypyridin-2-amine (3.5 g, 72percent) as an off-white solid. 1H-NMR (CD3OD, 400 MHz): δ 7.48 (d, 1H), 5.98 (d, 1H), 4.30 (s, 2H), 3.90 (s, 3H); LCMS: 205.2 (M+2); (column; X-Select CSH C-18 (50*3.0 mm, 3.5 μm); RT 3.52 min 0.05percent Aq TFA: ACN; 0.80 mL/min); TLC: 30percent EtOAc:hexanes (Rf: 0.5).
Reference: [1] Patent: US2012/122843, 2012, A1, . Location in patent: Page/Page column 15
[2] Patent: WO2015/109109, 2015, A1, . Location in patent: Paragraph 0711
[3] Patent: US2017/44182, 2017, A1, . Location in patent: Paragraph 0983
  • 2
  • [ 17920-35-3 ]
  • [ 1211533-83-3 ]
YieldReaction ConditionsOperation in experiment
74% With N-Bromosuccinimide In acetonitrile at 20℃; for 3 h; To a solution of 6-methoxypyridin-2-amine (10 g, 81 mmol) in acetonitrile (150 mL) was added N-bromosuccinimide (7.17 g, 40.3 mmol). The reaction mixture was stirred at rt for 90 mm. Additional N-bromosuccinimide (7.17 g, 40.3 mmol) in acetonitrile (35 mL) was added, and the reaction mixture was stirred at RT for another 90mm. The reaction mixture was diluted with water (250 mL) and extracted with EtOAc (2x 250 mL). Combined organic extracts were washed with water and brine, dried overNa2SO4 and concentrated. The cmde product was purified by flash chromatography(eluting with 10-15percent EtOAc in hexane) to give 5-bromo-6-methoxypyridin-2-amine(12.1 g, 74percent yield) as an off-white solid. MS(ESI) m/z: 205.3 (M+H) ‘H NMR (300MHz, chloroform-d) ö ppm 7.49 (d, J=8.0 Hz, 1 H), 5.99 (d, J8.0 Hz, 1 H), 4.31 (br. s., 2H), 3.91 (s, 3 H).
Reference: [1] Patent: WO2016/144936, 2016, A1, . Location in patent: Page/Page column 128
  • 3
  • [ 19798-81-3 ]
  • [ 1211533-83-3 ]
Reference: [1] Patent: US2012/122843, 2012, A1,
[2] Patent: WO2015/109109, 2015, A1,
[3] Patent: US2017/44182, 2017, A1,
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