Home Cart 0 Sign in  

[ CAS No. 356560-80-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 356560-80-0
Chemical Structure| 356560-80-0
Structure of 356560-80-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 356560-80-0 ]

Related Doc. of [ 356560-80-0 ]

Alternatived Products of [ 356560-80-0 ]

Product Details of [ 356560-80-0 ]

CAS No. :356560-80-0 MDL No. :MFCD08689534
Formula : C6H4BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :CXRXKDSDRWLKTK-UHFFFAOYSA-N
M.W :198.02 Pubchem ID :11513934
Synonyms :
6-Bromo[1,2,4]triazolo[1,5-a]pyridine

Calculated chemistry of [ 356560-80-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.69
TPSA : 30.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 1.44
Log Po/w (WLOGP) : 1.49
Log Po/w (MLOGP) : 1.76
Log Po/w (SILICOS-IT) : 1.2
Consensus Log Po/w : 1.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.453 mg/ml ; 0.00229 mol/l
Class : Soluble
Log S (Ali) : -1.68
Solubility : 4.14 mg/ml ; 0.0209 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.57
Solubility : 0.533 mg/ml ; 0.00269 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 356560-80-0 ]

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 [ 356560-80-0 ]

* 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 [ 356560-80-0 ]
  • Downstream synthetic route of [ 356560-80-0 ]

[ 356560-80-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 138888-98-9 ]
  • [ 356560-80-0 ]
YieldReaction ConditionsOperation in experiment
72% With pyridine; hydroxylamine-O-sulfonic acid In methanol at 0 - 20℃; for 12 h; Inert atmosphere To a solution of N'-(5-bromo-pyridin-2-yl)-N,N-dimethyl-formamidine (4 g, 1 7.54 mmol, 1 .00 equiv) in methanol (40 mL) maintained under nitrogen at 0 °C was added pyridine (4 mL, 2,00 equiv) and (aminooxy)sulfonic acid (3 , 6 g, 31 .83 mmol, 1 .30 equiv). The resulting solution was stirred for 1 2 h at rt. After the reaction completed, the mixture was concentrated under vacuum The residue was diluted with 1 50 mL of ethyl acetate then washed with 1 x50 mL of saturated aqeous sodium carbonate solution and 2x50 mL of water. The organic layer was dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was purified on a sil ica gel column eluted with ethyl acetate/hexane ( I ; 1 ) to give 2.5 g (72percent) title compound as a solid. LC/MS (Method D, ESI): RT= 1.1 min, m/z = 198.0 [M+H]
72% With pyridine; hydroxylamine-O-sulfonic acid In methanol at 0 - 20℃; for 12 h; Inert atmosphere To a solution of N'-(5- bromo-pyridin-2-yl)-N,N-dimethyl-formamidine (4 g, 1 7.54 mmol, 1 .00 equiv) in methanol (40 mL) maintained under nitrogen at 0 °C was added pyridine (4 mL, 2,00 equiv) and (aminooxy)sulfonic acid (3 , 6 g, 31 .83 mmol, 1 .30 equiv). The resulting solution was stirred for 1 2 h at rt. After the reaction completed, the mixture was concentrated under vacuum The residue was diluted with 1 50 mL of ethyl acetate then washed with 1 x50 mL of saturated aqeous sodium carbonate solution and 2x50 mL of water. The organic layer was dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was purified on a sil ica gel column eluted with ethyl acetate/hexane ( I ; 1 ) to give 2.5 g (72percent) title compound as a solid. LC/MS (Method D, ESI): RT= 1 . 1 min, m z = 198.0 [M+H] "
72% With pyridine; hydroxylamine-O-sulfonic acid In methanol at 0 - 20℃; for 12 h; Inert atmosphere To a solution of N'-(5-bromo-pyridin-2-yl)-N,N-dimethyl-formamidine (4 g, 17.54 mmol, 1.00 equiv) in MeOH (40 mL) maintained under nitrogen at 0 °C was added pyridine (4 mL, 2.00 equiv) and (aminooxy)sulfonic acid (3.6 g, 31 .83 mmol, 1.30 equiv). The resulting solution was stirred for 12 h at rt. After the reaction completed, the mixture was concentrated under vacuum. The residue was diluted with 150 mL of ethyl acetate then washed with 1x50 mL of saturated aqeous sodium carbonate solution and 2x50 mL of water. The organic layer was dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/hexane (1 : 1 ) to give 2.5 g (72percent) title compound as a solid. LC/MS (Method D, ESI): RT= 1.15 min, m/z = 198.0 [M+H] +.
72% at 0 - 20℃; for 12 h; Inert atmosphere [0206] Step 2. 6-Bromo-[1,2,4ltriazolo[1,5-alpyridine. To a solution of N’-(5-bromo- pyridin-2-yl)-N,N-dimethyl-formamidine (4 g, 17.54 mmol, 1.00 equiv) in methanol (40 mL) maintained under nitrogen at 0 °C was added pyridine (4 mL, 2.00 equiv) and (aminooxy)sulfonic acid (3.6 g, 31.83 mmol, 1.30 equiv). The resulting solution was stirred for 12 h at rt. After the reaction completed, the mixture was concentrated under vacuum. The residue was diluted with 150 mL of ethyl acetate then washed with 1x50 mL of saturated aqeous sodium carbonate solution and 2x50 mL of water. The organic layer was dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/hexane (1:1) to give 2.5 g (72percent) title compound as a solid. LC/MS (Method D, ESI): RT= 1.15 mi m/z = 198.0 [M+H].
72% With pyridine; hydroxylamine-O-sulfonic acid In methanol at 0 - 20℃; for 12 h; Inert atmosphere Step 2. 6-Bromo-rL2,41triazolorL5-alpyridine. To a solution of N'-(5-bromo- pyridin-2-yl)-N,N-dimethyl-formamidine (4 g, 17.54 mmol, 1.00 equiv) in methanol (40 mL) maintained under nitrogen at 0 °C was added pyridine (4 mL, 2.00 equiv) and (aminooxy) sulfonic acid (3.6 g, 31.83 mmol, 1.30 equiv). The resulting solution was stirred for 12 h at rt. After the reaction completed, the mixture was concentrated under vacuum. The residue was diluted with 150 mL of ethyl acetate then washed with 1x50 mL of saturated aqeous sodium carbonate solution and 2x50 mL of water. The organic layer was dried over anhydrous sodium sulfate then concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/hexane (1: 1) to give 2.5 g (72percent) title compound as a solid. LC/MS (Method D, ESI): RT= 1.15 min, m/z = 198.0 [M+H]+.

Reference: [1] Patent: WO2013/127266, 2013, A1, . Location in patent: Page/Page column 141
[2] Patent: WO2013/127267, 2013, A1, . Location in patent: Page/Page column 92
[3] Patent: WO2013/127268, 2013, A1, . Location in patent: Page/Page column 67
[4] Patent: WO2013/130935, 2013, A1, . Location in patent: Paragraph 0206
[5] Patent: WO2013/130943, 2013, A1, . Location in patent: Paragraph 0214
[6] Patent: WO2004/43940, 2004, A1, . Location in patent: Page 84
[7] Patent: WO2005/116029, 2005, A1, . Location in patent: Page/Page column 66
  • 2
  • [ 1075260-65-9 ]
  • [ 356560-80-0 ]
Reference: [1] Patent: WO2008/128953, 2008, A1, . Location in patent: Page/Page column 113-114
  • 3
  • [ 1072-97-5 ]
  • [ 356560-80-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 12, p. 3614 - 3627
[2] European Journal of Organic Chemistry, 2005, # 17, p. 3761 - 3765
[3] Patent: WO2013/127266, 2013, A1,
[4] Patent: WO2013/127267, 2013, A1,
[5] Patent: WO2013/127268, 2013, A1,
[6] Patent: WO2013/130935, 2013, A1,
[7] Patent: WO2013/130943, 2013, A1,
[8] Patent: WO2008/128953, 2008, A1,
[9] Patent: WO2004/43940, 2004, A1,
[10] Patent: WO2005/116029, 2005, A1,
  • 4
  • [ 356560-80-0 ]
  • [ 557-21-1 ]
  • [ 943845-23-6 ]
Reference: [1] Patent: EP2003132, 2008, A1, . Location in patent: Page/Page column 30
  • 5
  • [ 356560-80-0 ]
  • [ 73183-34-3 ]
  • [ 1160790-18-0 ]
YieldReaction ConditionsOperation in experiment
47% Inert atmosphere The A48-1 (180mg, 0.91mmol), bis (pinacolato) borate (348mg, 1.37mmol), 1,1'- bis (diphenylphosphino) ferrocene palladium (II)(37mg, 0.045mmol), potassium acetate (180mg, 1.83mmol) was dissolved in tetrahydrofuran (10mL). Under nitrogen for 8h at 80 , cooled toAt room temperature, filtered through celite, the solvent was evaporated under reduced pressure to give a dark solid (300mg, content: 74percent).
Reference: [1] Patent: CN105254613, 2016, A, . Location in patent: Paragraph 0349; 0350; 0351
[2] Patent: WO2009/74812, 2009, A1, . Location in patent: Page/Page column 36
[3] Patent: WO2010/20363, 2010, A1, . Location in patent: Page/Page column 87-88
  • 6
  • [ 356560-80-0 ]
  • [ 1043903-19-0 ]
Reference: [1] Patent: WO2013/127266, 2013, A1,
[2] Patent: WO2013/127267, 2013, A1,
[3] Patent: WO2013/127268, 2013, A1,
[4] Patent: WO2013/130935, 2013, A1,
[5] Patent: WO2013/130943, 2013, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 356560-80-0 ]

Bromides

Chemical Structure| 746668-59-7

[ 746668-59-7 ]

6-Bromo-5-methyl[1,2,4]triazolo[1,5-a]pyridine

Similarity: 0.91

Chemical Structure| 7169-95-1

[ 7169-95-1 ]

6-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine

Similarity: 0.91

Chemical Structure| 947248-68-2

[ 947248-68-2 ]

6-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Similarity: 0.91

Chemical Structure| 1053655-66-5

[ 1053655-66-5 ]

7-Bromo-[1,2,4]triazolo[1,5-a]pyridine

Similarity: 0.91

Chemical Structure| 882521-63-3

[ 882521-63-3 ]

7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Similarity: 0.83

Related Parent Nucleus of
[ 356560-80-0 ]

Other Aromatic Heterocycles

Chemical Structure| 746668-59-7

[ 746668-59-7 ]

6-Bromo-5-methyl[1,2,4]triazolo[1,5-a]pyridine

Similarity: 0.91

Chemical Structure| 7169-95-1

[ 7169-95-1 ]

6-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine

Similarity: 0.91

Chemical Structure| 947248-68-2

[ 947248-68-2 ]

6-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Similarity: 0.91

Chemical Structure| 1053655-66-5

[ 1053655-66-5 ]

7-Bromo-[1,2,4]triazolo[1,5-a]pyridine

Similarity: 0.91

Chemical Structure| 274-85-1

[ 274-85-1 ]

[1,2,4]Triazolo[1,5-a]pyridine

Similarity: 0.86