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[ CAS No. 117719-17-2 ] {[proInfo.proName]}

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Chemical Structure| 117719-17-2
Chemical Structure| 117719-17-2
Structure of 117719-17-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 117719-17-2 ]

CAS No. :117719-17-2 MDL No. :MFCD08056165
Formula : C8H11BrN4O Boiling Point : -
Linear Structure Formula :- InChI Key :CWVGSOUZYXNHLF-UHFFFAOYSA-N
M.W : 259.10 Pubchem ID :16740441
Synonyms :

Calculated chemistry of [ 117719-17-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.86
TPSA : 64.27 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 0.54
Log Po/w (WLOGP) : 0.29
Log Po/w (MLOGP) : 0.08
Log Po/w (SILICOS-IT) : 0.88
Consensus Log Po/w : 0.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.04
Solubility : 2.38 mg/ml ; 0.00917 mol/l
Class : Soluble
Log S (Ali) : -1.46
Solubility : 8.96 mg/ml ; 0.0346 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.33
Solubility : 1.2 mg/ml ; 0.00462 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.72

Safety of [ 117719-17-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 117719-17-2 ]

* 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 [ 117719-17-2 ]
  • Downstream synthetic route of [ 117719-17-2 ]

[ 117719-17-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 110-91-8 ]
  • [ 24241-18-7 ]
  • [ 117719-17-2 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: at 120℃; for 48 h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
A solution of intermediate 1-01(15 g, 59.3 mmol) in morpholine (15 ml, 178 mmol) was heated at 120°C in a Parr reactor for 48h. A brown solid appears. The solid was suspended in DCM and washed with NaHC03 aq. sat (twice). The organic phase was dried (NaS04), filtered and evaporated to dryness to obtain I-02, 14.8 g of a brown solid (Y: 96 percent).
96% at 120℃; for 48 h; Preparation of Intermediate I-02. A solution of intermediate I-01(15 g, 59.3 mmol) in morpholine (15 ml, 178 mmol) was heated at 120° C. in a Parr reactor for 48 h. A brown solid appears. The solid was suspended in DCM and washed with NaHCO3 aq. sat (twice). The organic phase was dried (NaSO4), filtered and evaporated to dryness to obtain 1-02, 14.8 g of a brown solid (Y: 96percent)
96.1% for 1 h; Reflux A mixture of morpholine (50 mL) and 3,5-dibromo-2-aminopyrazine (12.50 g) was refluxed for 1 h until the reaction was complete by TLC analysis. The solution was cooled to room temperature andadded to a beaker containing ice water (300 mL) with continuous stirring. The solid was precipitated and filtered. After drying, 12.30 g of a yellow solid with a metallic luster was obtained (a yield of 96.1percent). 1H-NMR (DMSO-d6) δ 7.70 (s, 1H), 6.28 (s, 2H), 3.85–3.62 (m, 4H), 3.04 (d, J = 4.0 Hz, 4H).
96.1% at 80℃; for 1 h; Morpholine (50 mL) was added to a three-necked flask containing 12.50 g of 3,5-dibromo-2-aminopyrazine and maintained at 80 ° CThe reaction was completed by the reaction of TLC for 1 h. The refluxed system was cooled to room temperature and added to a mixture containing ice water (300 mL)The mixture was stirred and dried to give 12.30 g of a yellow solid with metallic luster, i.e., 3-morpholine-5-Bromo-2-aminopyrazine in a yield of 96.1percent.
96% at 120℃; for 48 h; A solution of intermediate 1-01(15 g, 59.3 mmol) inmorpholine (15 ml, 178 mmol) was heated at 120° C. in a Parr reactor for 48 h. A brown solid appears. The solid was suspended in DCM and washed with NaHCO3 aq. sat (twice). The organic phase was dried (NaSO4), filtered and evaporated to dryness to obtain 1-02, 14.8 g of a brown solid(Y: 96percent)
86.7% at 80℃; for 6 h; A 500ml three-neck flask, was added morpholine (9.6g, 0.11mol) and 2-amino-3,5-dibromo-pyrazine (25.3g, 0.1mol) and N- methylpyrrolidinone (100ml), and at 80 reaction 6h, TLC tracking, cooled to room temperature, add water 400ml, stirring, suction filtered and dried to give a yellow solid 22.5g, a yield of 86.7percent.
74%
Stage #1: at 120℃; for 24 h;
Stage #2: With sodium carbonate In dichloromethane; water
Preparation of intermediate 11-1; A solution of product 2-amino-3,5-dibromo-4-ylpyrazine (cas: 117719-17-2), (40 g, 158 mmol, 1.0 eq) in morpholine (41.5 ml, 474 mmol 3.0 eq) was heated at 120°C in a parr reactor for 24h. A brown solid appears. The solid was suspended in DCM and washed with Na2C03 aq. sat (twice). The organic phase was dried (MgS04), filtered and solvent removed in vacuo to give a brown solid, which was triturated from Et20 to afford the desired product (30.54 g, 74percent) as a pale brown solid as 11-1.

Reference: [1] Patent: WO2011/36461, 2011, A1, . Location in patent: Page/Page column 77
[2] Tetrahedron Letters, 2012, vol. 53, # 9, p. 1082 - 1084
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 1874 - 1878
[4] Patent: US2012/83492, 2012, A1, . Location in patent: Page/Page column 91
[5] Molecules, 2017, vol. 22, # 2,
[6] Patent: CN106831812, 2017, A, . Location in patent: Paragraph 0137; 0138; 0139
[7] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4794 - 4799
[8] Patent: US9993554, 2018, B2, . Location in patent: Page/Page column 49; 241; 242
[9] Patent: CN105622526, 2016, A, . Location in patent: Paragraph 0026; 0027; 0028
[10] Patent: WO2011/89400, 2011, A1, . Location in patent: Page/Page column 117
[11] Patent: CN108570011, 2018, A, . Location in patent: Paragraph 0012; 0013; 0014
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