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[ CAS No. 663194-10-3 ] {[proInfo.proName]}

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Chemical Structure| 663194-10-3
Chemical Structure| 663194-10-3
Structure of 663194-10-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 663194-10-3 ]

CAS No. :663194-10-3 MDL No. :MFCD03861153
Formula : C8H10BrN3O Boiling Point : -
Linear Structure Formula :- InChI Key :AVLAJWPBZJNJDQ-UHFFFAOYSA-N
M.W : 244.09 Pubchem ID :45787495
Synonyms :

Calculated chemistry of [ 663194-10-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.46
TPSA : 38.25 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) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.19
Log Po/w (XLOGP3) : 1.84
Log Po/w (WLOGP) : 0.69
Log Po/w (MLOGP) : 0.64
Log Po/w (SILICOS-IT) : 1.62
Consensus Log Po/w : 1.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.79
Solubility : 0.398 mg/ml ; 0.00163 mol/l
Class : Soluble
Log S (Ali) : -2.26
Solubility : 1.33 mg/ml ; 0.00545 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.7
Solubility : 0.49 mg/ml ; 0.00201 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.31

Safety of [ 663194-10-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 663194-10-3 ]

* 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 [ 663194-10-3 ]
  • Downstream synthetic route of [ 663194-10-3 ]

[ 663194-10-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 19810-79-8 ]
  • [ 663194-10-3 ]
YieldReaction ConditionsOperation in experiment
87% With phosphorus(V) oxybromide In acetonitrile for 1 h; Heating / reflux 2c) 4- (4-BROMO-PVRIMIDIN-2-VL)-MORPHOLINE A mixture of 2-morpholin-4-yl-pyrimidin-4-ol (6.08 g, 33.6 MMOL) and phosphorus OXYBROMIDE (12.5 g, 43.7 MMOL) in 330 mL MECN is heated to reflux for 1 hour. The reaction is cooled to room temperature, concentrated to half volume, and poured over ice. The resulting mixture is neutralized with a saturated solution of NaHCOs, and then extracted with methylene chloride. The organic phase is washed with saturated NACI (aqueous), dried over ANHYDROUS MGS04, FILTERED, concentrated and dried to an off-white solid (7.11 g, 87percent). M+H'= 245.97. H NMR (CDC13) ; a 8.05 (d, 1H), 6.70 (d, 1H), 3.75 (m, 8H).
Reference: [1] Patent: WO2005/28444, 2005, A1, . Location in patent: Page/Page column 50-51
  • 2
  • [ 110-91-8 ]
  • [ 3921-01-5 ]
  • [ 663194-10-3 ]
  • [ 1209459-32-4 ]
YieldReaction ConditionsOperation in experiment
19%
Stage #1: With potassium carbonate In tetrahydrofuran at 20℃; for 0.0833333 h;
Stage #2: at 20℃;
2,4-dibromopyrimidine (438.4mg, 1.84mmol) and potassium carbonate (1.27g, 9.21mmol) in tetrahydrofuran (10mL) were added together and stirred at room temperature for 5min. Morpholine (174.8μL, 2.03mmol) was then added dropwise and the solution continued to stir at room temperature for 5h. The reaction mixture was filtered and the filtrate was collected and then concentrated under reduced pressure. The products were purified by silica column chromatography in hexanes and ethyl acetate to afford 28a and 28b in 19percent and 66percent yields, respectively. (0070) 4-(4-bromopyrimidin-2-yl)morpholine (28a). (White solid, Yield: 19percent). 1H NMR (500MHz, CDCl3) δ ppm 3.74–3.77 (m, 4H) 3.79–3.83 (m, 4H) 6.70 (d, J=4.88Hz, 1H) 8.05 (d, J=4.88Hz, 1H). LCMS found 246.0, [M+H]+. (0071) 4-(2-bromopyrimidin-4-yl)morpholine (28b). (White solid, Yield: 66percent) 1H NMR (500MHz, CDCl3) δ ppm 3.66 (br. s., 4H) 3.76–3.83 (m, 4H) 6.43 (d, J=6.35Hz, 1H) 8.02 (d, J=6.35Hz, 1H). LCMS found 246.0, [M+H]+.
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 141, p. 446 - 459
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