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[ CAS No. 24241-18-7 ] {[proInfo.proName]}

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Chemical Structure| 24241-18-7
Chemical Structure| 24241-18-7
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Product Details of [ 24241-18-7 ]

CAS No. :24241-18-7 MDL No. :MFCD00673150
Formula : C4H3Br2N3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :DTLBKXRFWUERQN-UHFFFAOYSA-N
M.W : 252.89 Pubchem ID :620004
Synonyms :
Chemical Name :2-Amino-3,5-dibromopyrazine

Calculated chemistry of [ 24241-18-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.84
TPSA : 51.8 ?2

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) : -6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 1.48
Log Po/w (WLOGP) : 1.59
Log Po/w (MLOGP) : 0.55
Log Po/w (SILICOS-IT) : 1.71
Consensus Log Po/w : 1.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.83
Solubility : 0.371 mg/ml ; 0.00147 mol/l
Class : Soluble
Log S (Ali) : -2.17
Solubility : 1.69 mg/ml ; 0.00669 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.251 mg/ml ; 0.000993 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.46

Safety of [ 24241-18-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335-H302+H312+H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 24241-18-7 ]

* 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 [ 24241-18-7 ]
  • Downstream synthetic route of [ 24241-18-7 ]

[ 24241-18-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 70-23-5 ]
  • [ 24241-18-7 ]
  • [ 87597-21-5 ]
YieldReaction ConditionsOperation in experiment
50.6% at 20 - 110℃; Step A: Preparation of ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylateTo a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10 C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over a2(S04) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 percent) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz, CDCl3): δ =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.
50.6% at 110℃; for 3 h; Step A: Preparation of ethyl 6,8-dibromoimidazo[ 1 , 2-a]pyrazine-2-carboxylateTo a stirred solution of 2-amino-3, 5-dibrompyrazine (20 g, 79mmol) in dimethyicarbonate (1 33 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10° C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na2(S04) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 percent) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz, CDC ): δ =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.
50.6% at 20 - 110℃; for 3 h; Intermediate Example 1 -2: Preparation of (6,8-dibromoimidazo[1 ,2-a]pyrazin-2- yl)methanolStep A: Preparation of ethyl 6,8-dibromoimidazo[1 , 2-a]pyrazi'ne-2-carboxylateTo a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10° C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over a2(S04) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 percent) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz, CDCI3): δ =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.
50.6% at 110℃; Step A: Preparation of ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylateTo a stirred solution of 2-amino-3,5-di brom pyrazi ne (20 g, 79m mol ) i n dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 1 10° C for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na2(S04) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6 3/4) ethyl 6,8-dibromoimidazo[1 ,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz, CDCl3): δ =8.30 (s, 1 H), 8.27 (s, 1 H), 4.48 (q, 2H), 1 .43 (tr, 3H) ppm.
50.6% at 20 - 110℃; To a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79 mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 110° C. for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na2(SO4) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6percent) ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz,
50.6% at 110℃; for 3 h; To a stirred solution of 2-amino-3,5-dibrompyrazine (20 g, 79 mmol) in dimethylcarbonate (133 mL) at rt was added ethyl 3-bromo-2-oxopropanoate (17.14 g, 79 mmol) in one portion. After stirring at 110° C. for 3 h, the solution was stirred at rt overnight. Water and DCM were added and the aqueous phase was extracted with DCM. After washing of the organic phase with water, drying over Na2(SO4) and filtration the organic phase was evaporated. Flash chromatography yielded 13.95 g (50.6percent) ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate: 1H-NMR (300 MHz, CDCl3: δ=8.30 (s, 1H), 8.27 (s, 1H), 4.48 (q, 2H), 1.43 (tr, 3H) ppm.

Reference: [1] Patent: WO2012/80232, 2012, A1, . Location in patent: Page/Page column 36-37
[2] Patent: WO2012/80228, 2012, A1, . Location in patent: Page/Page column 42-43
[3] Patent: WO2012/80234, 2012, A1, . Location in patent: Page/Page column 45
[4] Patent: WO2012/80236, 2012, A1, . Location in patent: Page/Page column 64
[5] Patent: US2013/281460, 2013, A1, . Location in patent: Paragraph 0270-0271
[6] Patent: US2013/267527, 2013, A1, . Location in patent: Paragraph 0245-0246
  • 2
  • [ 65868-37-3 ]
  • [ 24241-18-7 ]
  • [ 87597-21-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 2, p. 206 - 212
  • 3
  • [ 24241-18-7 ]
  • [ 1416740-16-3 ]
YieldReaction ConditionsOperation in experiment
88.7% at 10 - 20℃; for 1.5 h; Step 3: 2-bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine[00199] 2-bromo-5H-pyrrolo[2,3-b]pyrazine (20 g, 101.0 mmol) was dissolved in ice-cold sulfuric acid (140.0 mL) , producing a bright orange solution, and concentrated nitric acid (12.73 g, 8.470 mL, 202.0 mmol) was added drop wise with stirring over 30 min keeping the temperature under 10 °C (turning the solution to a clear red colour). The reaction was removed from the ice bath after 30 min and allowed to warm to ambient temperature and left to stir at ambient temperature for 1 hour. The reaction mixture was poured onto ice to obtain a yellow solid. The solid was filtered, washed with water to give 2-bromo-7-nitro-5H- pyrrolo[2,3-b]pyrazine the desired product as a yellow solid. (21.76 g, 88.7percent). MS (ES+) 244.87.
Reference: [1] Patent: WO2012/178123, 2012, A1, . Location in patent: Page/Page column 64
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