Home Cart 0 Sign in  
X

[ CAS No. 947248-68-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 947248-68-2
Chemical Structure| 947248-68-2
Chemical Structure| 947248-68-2
Structure of 947248-68-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 947248-68-2 ]

Related Doc. of [ 947248-68-2 ]

Alternatived Products of [ 947248-68-2 ]

Product Details of [ 947248-68-2 ]

CAS No. :947248-68-2 MDL No. :MFCD11656619
Formula : C6H5BrN4 Boiling Point : -
Linear Structure Formula :- InChI Key :XHBQNLHFUPSZNL-UHFFFAOYSA-N
M.W :213.04 Pubchem ID :25215940
Synonyms :

Calculated chemistry of [ 947248-68-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.09
TPSA : 56.21 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) : -6.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 1.09
Log Po/w (WLOGP) : 1.08
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 0.45
Consensus Log Po/w : 1.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.45
Solubility : 0.751 mg/ml ; 0.00352 mol/l
Class : Soluble
Log S (Ali) : -1.86
Solubility : 2.92 mg/ml ; 0.0137 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.21
Solubility : 1.3 mg/ml ; 0.00612 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.87

Safety of [ 947248-68-2 ]

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 [ 947248-68-2 ]

* 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 [ 947248-68-2 ]
  • Downstream synthetic route of [ 947248-68-2 ]

[ 947248-68-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1010120-60-1 ]
  • [ 947248-68-2 ]
YieldReaction ConditionsOperation in experiment
99% With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In methanol; ethanol at 20 - 70℃; for 5 h; Step b) Formation of 6-bromo[1 ,2,4]triazolo[1 ,5-a]pyridin-2-amine A suspension of ethyl [(5-bromopyridin-2-yl)amino]carbonothioyl}carbamate (12.3 g,40.4 mmol), hydroxylamine hydrochloride (14.1 g, 202 mmol) and DIEA (15.7 g, 122 mmol) in a mixture of MeOH and EtOH (ratio 1 :1 , 200 ml.) was stirred at RT for 2 hours and then at 700C for 3 hours. The solvents were removed under reduced pressure. The residue was taken up in dioxane/water (1 :1 ) and filtered to give the title compound as an off-white powder (42.6 g, 99percent). HPLC, Rt: 1.1 min (purity 99.8percent). LC/MS, M+(ESI): 215.3.
99% With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In methanol; ethanol at 20 - 70℃; A suspension of ethyl [(5-bromopyridin-2-yl)amino]carbonothioyl}carbamate (12.3 g, 40.4 mmol), hydroxylamine hydrochloride (14.1 g, 202 mmol) and DIEA (15.7 g, 122 mmol) in a mixture of MeOH and EtOH (ratio 1 :1 , 200 ml_) was stirred at RT for 2 hours and then at 700C for 3 hours. The solvents were removed under reduced pressure. The residue was taken up in dioxane/water (1 :1 ) and filtered to give the title compound as an off-white powder (42.6 g, 99percent). HPLC, Rt: 1.1 min (purity 99.8percent). LC/MS, M+(ESI): 215.3.
96% With hydroxylamine hydrochloride; diisopropylamine In methanol; ethanol at 20 - 60℃; for 5 h; 12.83 g (184.632 mmol) of hydroxylamine hydrochloride and 14.32 g (110.779 mmol) N,N- diisopropylamine were dissolved in 70 ml methanol/ethanol (v/v = 1:1). .sect.0.4 g of the compound from example 105 A was added and the mixture was stirred at room temperature for 2 h and at 60°C for 3 h. After cooling, water and ethyl acetate were added, the organic phase was removed and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, concentrated in a rotary evaporator and the residue was dried under high vacuum. We obtained 7.02 g (96percent of theor.) of the target compound.GC-MS (method 6): R, = 6.11 min; MS (EIpos): m/z = 212 [M]+. 1H-NMR (400 MHz, DMSO-D6): δ [ppm] = 6.13 (s, 2H), 7.33 (d, IH), 7.55 (dd, IH), 8.92 (d, IH).
85% With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In ethanol at 25℃; Reflux b) 6-Bromo-[ 1 ,2,4] triazolo[ 1 ,5-a]pyridin-2-ylamineA mixture of hydroxylamine hydrochloride (40.0 g, 575 mmol) and N- ethyldiisopropylamine (44.6 g, 60.3 ml, 345 mmol) in ethanol (734 ml) was stirred for a few minutes at 25 °C, then the mixture was added to l-ethoxycarbonyl-3-(5-bromo-pyridin-2-yl)- thiourea (35 g, 115 mmol) and the resulting mixture was refluxed for 1 day. The solvent was evaporated under reduced pressure and the white solid was treated with 400 ml water. The suspension was stirred for 1 hour, the solid was filtered off, washed with water 3 times and dried under reduced pressure, affording 6-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (21 g, 85percent) as white solid. Mp.: 185°C. MS: m/z=213.0/215.1 (M+H+).
69% With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In methanol; ethanol for 2 h; Heating / reflux 2.2 6-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (3) To a suspension of hydroxylamine hydrochloride (409.2 g, 5.888 mol) in EtOH/MeOH (1 :1, 2.5 L) was added JV,jV-diisopropylethylamine (606.1 mL, 3.480 mol), the mixture was stirred at room temperature (20 0C) for 1 h. l-(6-Bromo-pyridin-2-yl)-3-carboethoxy-thiourea (2) (352.8 g, 1.160 mol) was then added and the mixture slowly heated to reflux (Note: bleach scrubber required to quench H2S evolved). After 2 h at reflux the mixture was allowed to cool and filtered to collect the precipitated solid. The collected solid was washed successively with <n="45"/>water (1.0 L), EtOH/MeOH (1 :1, 1.0 L) and diethyl ether (500 niL) then air-dried to afford the title compound as a white solid (169.2 g, 69 percent). No further purification was required.1H NMR (de-DMSO) δ 8.94 (d, IH), 7.58 (dd, IH), 7.36 (d, IH), 6.16 (br s, 2H). m/z 213/215 (1 :1, M+H+, 100percent).
60.9% at 20 - 60℃; for 4.5 h; 6-Bromo-[1 ,2,4]triazolo[1 ,5-a]pyridln-2-amine (PZ972-2): DMAP (2.82 g, 23.1 mmol) was added to a mixture of PZ972-1 (2.34 g, 7.7 mmol), hydroxylamine HCl salt (2.67 g, 38.5 mmol) in methanol/ethanol (20 mL 20 mL). The reaction was stirred at rt for 1.5 h, then at 60 °C for 3 h. The solvent was removed under vacuum, and the resulting residue was partitioned between dichloromethane (30 mL) and water (30 mL). The water phase was extracted with dichloromthane (30 mLx2). The organic phases were collected, dried over anhydrous sodium sulfate, and concentrated. The crude product was washed with petroleum ether to get PZ972-2 (1 g, 60.9percent). LC-MS: 213.2, 215.2 (M+l).
19.3 g With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In methanol; ethanol at 60℃; for 2 h; Hydroxylammoniumchlorid (39.8 g) was suspended in methanol (200 mL) and ethanol (190 mL) and Hiinig Base (59 mL) was added at r.t. The mixture was heated to 60°C, Int01.01 (30 g) was added portionwise, and the mixture was stirred at 60 °C for 2h. The solvent was removed in vacuum and water (150 mL) was added. A solid was collected by filtration and was washed with water and dried in vacuum. Yield: 19.3 g of the title compound. 1H-NMR (300MHz, DMSO-d6): δ [ppm]= 6.10 (s, 2H), 7.28 (dd, 1H), 7.51 (dd, 1H), 8.88 (dd, 1H).
19.3 g With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In methanol; ethanol at 60℃; for 2 h; Hydroxylammonium chloride (39.8 g) was suspended in methanol (200 mL) and ethanol (190 mL) and Hiinig Base (59 mL) was added at r.t. The mixture was heated to 60°C, Int01.01 (30 g) was added portionwise, and the mixture was stirred at 60° C for 2h. The solvent was removed in vacuum and water (150 mL) was added. A solid was collected by filtration and was washed with water and dried in vacuum. Yield: 19.3 g of the title compound. 1H-NMR (300MHz, DMSO-d6): δ [ppm] = 6.10 (s, 2H), 7.28 (dd, 1 H), 7.51 (dd, 1 H), 8.88 (dd, 1 H).
19.3 g With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In methanol; ethanol at 60℃; for 2 h; Inert atmosphere Hydroxylammoniumchlorid (39.8 g) was suspended in methanol (200 mL) and ethanol (190 mL) and Hunig Base (59 mL) was added at r.t. The mixture was heated to 60°C, Int01 .01 (30 g) was added portionwise, and the mixture was stirred at 60 °C for 2h. The solvent was removed in vacuum and water (150 mL) was added. A solid was collected by filtration and was washed with water and dried in vacuum. Yield: 19.3 g of the title compound. 1H-NMR (300MHz, DMSO-d6): δ [ppm]= 6.10 (s, 2H), 7.28 (dd, 1 H), 7.51 (dd, 1 H), 8.88 (dd, 1 H).
19.3 g With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In methanol at 60℃; for 2 h; Hydroxylammonium chloride (39.8 g) was suspended in methanol (200 mL), and ethanol (190 mL) and Hiinig Base (59 mL) were added at r.t. The mixture was heated to 60°C, Int01.01 (30 g) was added portionwise, and the mixture was stirred at 60 °C for 2h. The solvent was removed in vacuum, and water (150 mL) was added. A solid was collected by filtration and was washed with water and dried in vacuum. Yield: 19.3 g of the title compound.1H-NMR (300MHz, DMSO-d6): δ [ppm] = 6.10 (s, 2H), 7.28 (dd, 1 H), 7.51 (dd,1 H), 8.88 (dd, 1 H).
19.3 g With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In methanol; ethanol at 60℃; for 2 h; Hydroxylammonium chloride (39.8 g) was suspended in methanol (200 mL) and ethanol (190 mL) and Hünig Base (59 mL) was added at r.t. The mixture was heated to 60°C, IntOl.01 (30 g) was added portionwise, and the mixture was stirred at 60°C for 2h. The solvent was removed in vacuum and water (150 mL)was added. A solid was collected by filtration and was washed with water and dried in vacuum.Yield: 19.3 g of the title compound.1H-NMR (300MHz, DMSO-d6): 6 [ppm] = 6.10 (5, 2H), 7.28 (dd, 1H), 7.51 (dd, 1H), 8.88 (dd, 1H).
19.3 g With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In methanol; ethanol at 60℃; for 2 h; Hydroxylammonium chloride (39.8 g) was suspended in methanol (200 mL) and ethanol (190 mL) and Hünig Base (59 mL) was added at r.t.
The mixture was heated to 60° C., Int01.01 (30 g) was added portionwise, and the mixture was stirred at 60° C. for 2 h.
The solvent was removed in vacuum and water (150 mL) was added.
A solid was collected by filtration and was washed with water and dried in vacuum.
Yield: 19.3 g of the title compound.
1H-NMR (300 MHz, DMSO-d6): δ [ppm]=6.10 (s, 2H), 7.28 (dd, 1H), 7.51 (dd, 1H), 8.88 (dd, 1H).

Reference: [1] Patent: WO2010/100144, 2010, A1, . Location in patent: Page/Page column 102-103
[2] Patent: WO2009/133127, 2009, A1, . Location in patent: Page/Page column 85
[3] Patent: WO2010/20363, 2010, A1, . Location in patent: Page/Page column 126-127
[4] Patent: WO2013/41472, 2013, A1, . Location in patent: Page/Page column 36
[5] Patent: WO2009/68482, 2009, A1, . Location in patent: Page/Page column 43-44
[6] Patent: WO2012/130299, 2012, A1, . Location in patent: Page/Page column 130
[7] Patent: WO2011/64328, 2011, A1, . Location in patent: Page/Page column 63-64
[8] Patent: WO2011/63908, 2011, A1, . Location in patent: Page/Page column 53-54
[9] Patent: EP2343295, 2011, A1, . Location in patent: Page/Page column 23
[10] Patent: EP2343297, 2011, A1, . Location in patent: Page/Page column 25
[11] Patent: WO2011/157688, 2011, A1, . Location in patent: Page/Page column 92
[12] ChemMedChem, 2011, vol. 6, # 12, p. 2214 - 2224
[13] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 16, p. 5257 - 5263
[14] Patent: WO2012/143329, 2012, A1, . Location in patent: Page/Page column 73
[15] Patent: WO2012/160029, 2012, A1, . Location in patent: Page/Page column 69-70
[16] Patent: WO2013/87579, 2013, A1, . Location in patent: Page/Page column 93; 94
[17] Patent: WO2014/9219, 2014, A1, . Location in patent: Page/Page column 68
[18] Patent: WO2014/20041, 2014, A1, . Location in patent: Page/Page column 125
[19] Patent: WO2014/195276, 2014, A1, . Location in patent: Page/Page column 96
[20] Patent: WO2014/198647, 2014, A2, . Location in patent: Page/Page column 71
[21] Patent: US2015/148542, 2015, A1, . Location in patent: Paragraph 0325-0328
[22] Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 2, p. 257 - 261
  • 2
  • [ 1010120-60-1 ]
  • [ 5470-11-1 ]
  • [ 947248-68-2 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With N-ethyl-N,N-diisopropylamine In methanol; ethanol at 20℃; for 1 h;
Stage #2: Reflux
Step 2; To a solution of hydroxylamine hydrochloride (345 mg) in ethanol-methanol (1:1) (10 mL), diisopropylethylamine (0.5 mL) was added. The solution was then stirred at room temperature for 1 hour. To the solution, 55 (303 mg, 1 mmol) was added, followed by reflux. After the starting material was consumed, the reaction mixture was cooled. The precipitate was collected by filtration, and then washed sequentially with water, ethanol-methanol (1:1), and diethyl ether to yield target compound 56 (100 mg, y. 51percent). 1H-NMR (300 Mz) (DMSO): 6.13 (s, 2H), 7.02 (d, J = 9 Hz, 1H), 7.54 (d, J = 9 Hz, 1H), 8.92 (s, 1H).
Reference: [1] Patent: EP2426135, 2012, A1, . Location in patent: Page/Page column 113
  • 3
  • [ 1072-97-5 ]
  • [ 947248-68-2 ]
Reference: [1] Patent: WO2011/63908, 2011, A1,
[2] Patent: WO2012/143329, 2012, A1,
[3] Patent: EP2343295, 2011, A1,
[4] Patent: WO2011/64328, 2011, A1,
[5] Patent: EP2343297, 2011, A1,
[6] Patent: WO2012/160029, 2012, A1,
[7] Patent: WO2011/157688, 2011, A1,
[8] Patent: EP2426135, 2012, A1,
[9] ChemMedChem, 2011, vol. 6, # 12, p. 2214 - 2224
[10] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 16, p. 5257 - 5263
[11] Patent: WO2012/130299, 2012, A1,
[12] Patent: WO2013/87579, 2013, A1,
[13] Patent: WO2014/9219, 2014, A1,
[14] Patent: WO2014/20041, 2014, A1,
[15] Patent: WO2014/195276, 2014, A1,
[16] Patent: WO2014/198647, 2014, A2,
[17] Patent: US2015/148542, 2015, A1,
[18] Patent: WO2013/41472, 2013, A1,
[19] Patent: WO2009/133127, 2009, A1,
[20] Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 2, p. 257 - 261
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 947248-68-2 ]

Bromides

Chemical Structure| 882521-63-3

[ 882521-63-3 ]

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

Similarity: 0.91

Chemical Structure| 356560-80-0

[ 356560-80-0 ]

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

Similarity: 0.91

Chemical Structure| 746668-59-7

[ 746668-59-7 ]

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

Similarity: 0.84

Chemical Structure| 7169-95-1

[ 7169-95-1 ]

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

Similarity: 0.84

Chemical Structure| 1053655-66-5

[ 1053655-66-5 ]

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

Similarity: 0.83

Amines

Chemical Structure| 882521-63-3

[ 882521-63-3 ]

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

Similarity: 0.91

Chemical Structure| 1124382-72-4

[ 1124382-72-4 ]

2-Amino-8-bromo[1,2,4]triazolo[1,5-a]pyridine

Similarity: 0.81

Chemical Structure| 1092394-16-5

[ 1092394-16-5 ]

2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-ol hydrobromide

Similarity: 0.80

Chemical Structure| 1010120-55-4

[ 1010120-55-4 ]

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

Similarity: 0.79

Chemical Structure| 1239647-60-9

[ 1239647-60-9 ]

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

Similarity: 0.78

Related Parent Nucleus of
[ 947248-68-2 ]

Other Aromatic Heterocycles

Chemical Structure| 882521-63-3

[ 882521-63-3 ]

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

Similarity: 0.91

Chemical Structure| 356560-80-0

[ 356560-80-0 ]

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

Similarity: 0.91

Chemical Structure| 746668-59-7

[ 746668-59-7 ]

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

Similarity: 0.84

Chemical Structure| 7169-95-1

[ 7169-95-1 ]

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

Similarity: 0.84

Chemical Structure| 1053655-66-5

[ 1053655-66-5 ]

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

Similarity: 0.83