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[ CAS No. 6693-08-9 ] {[proInfo.proName]}

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Chemical Structure| 6693-08-9
Chemical Structure| 6693-08-9
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Product Details of [ 6693-08-9 ]

CAS No. :6693-08-9 MDL No. :MFCD11040435
Formula : C4Cl3FN2 Boiling Point : -
Linear Structure Formula :- InChI Key :XXBZSPPWTVRISV-UHFFFAOYSA-N
M.W : 201.41 Pubchem ID :13388993
Synonyms :

Calculated chemistry of [ 6693-08-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.02
TPSA : 25.78 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) : -5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : 3.19
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 1.86
Log Po/w (SILICOS-IT) : 3.45
Consensus Log Po/w : 2.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.54
Solubility : 0.0578 mg/ml ; 0.000287 mol/l
Class : Soluble
Log S (Ali) : -3.4
Solubility : 0.0797 mg/ml ; 0.000396 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.79
Solubility : 0.033 mg/ml ; 0.000164 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 6693-08-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6693-08-9 ]

* 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 [ 6693-08-9 ]
  • Downstream synthetic route of [ 6693-08-9 ]

[ 6693-08-9 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 6693-08-9 ]
  • [ 2927-71-1 ]
Reference: [1] Journal of Fluorine Chemistry, 1989, vol. 45, p. 417 - 430
  • 2
  • [ 6693-08-9 ]
  • [ 62802-42-0 ]
Reference: [1] Journal of Fluorine Chemistry, 1989, vol. 45, p. 417 - 430
  • 3
  • [ 767-80-6 ]
  • [ 6693-08-9 ]
Reference: [1] Patent: WO2011/50200, 2011, A1, . Location in patent: Page/Page column 90
[2] Patent: WO2011/50202, 2011, A1, . Location in patent: Page/Page column 61-62
[3] Patent: WO2012/145581, 2012, A1, . Location in patent: Page/Page column 83
  • 4
  • [ 767-80-6 ]
  • [ 6693-08-9 ]
YieldReaction ConditionsOperation in experiment
28% at 100 - 110℃; for 4 - 8 h; Part B: 2,4,6-Trichloro-5-fluoropyrimidine. Finely powdered 5-fluoro-6-hydroxy-2,4(1H,3H)-pyrimidinedione (74 g, 0.507 mol) was added portionwise over 30 min to POCI3 (232 mL, 2.5 mol) with stirring (exothermic). Upon complete addition, the mixture was held at 60 0C while N,N,-dimethylaniline (65 mL) was added dropwise by syringe. After addition, the mixture was heated to 100-1 10 0C (internal) until the reaction was judged complete, usually in 4-8 h. The mixture was cooled and the bulk of the remaining POCI3 was removed by careful vacuum distillation at 80-90 0C (some product can be detected in the POCI3 distillate). The remaining residue was poured onto ice (-1 L) and stirred for 30 min, then extracted with ether (1 x 400 mL, 2 x 150 mL). The combined extracts were washed with water and brine, then dried (MgSO4). Filtration and atmospheric distillation of the ether provided the crude product, which was distilled under reduced pressure to provide the product (28.8 g, 28percent) as a low melting white crystalline solid (b.p. 80-85 0C, 12 mm). LCMS: (M+H) +: not detected.
28% at 60 - 110℃; Inert atmosphere Part B: 2,4,6-Trichloro-5-fluoropyrimidine Finely powdered 5-fluoro-6-hydroxy-2,4(1 H,3/-/)-pyrimidinedione (74 g, 0.507 mol) was added portionwise over 30 min to POCI3 (232 mL, 2.5 mol) with stirring (exothermic). Upon complete addition, the mixture was held at 60 °C while Ν,Ν,- dimethylaniline (65 mL) was added dropwise by syringe. After addition, the mixture was heated to 100-1 10 °C (internal) until the reaction was judged complete, usually in 4-8 h. The mixture was cooled and the bulk of the remaining POCI3 was removed by careful vacuum distillation at 80-90 °C (some product can be detected in the POCI3 distillate). The remaining residue was poured onto ice (-1 L) and stirred for 30 min, then extracted with ether (1 x 400 mL, 2 x 150 mL). The combined extracts were washed with water and brine, then dried (MgS04). Filtration and atmospheric distillation of the ether provided the crude product, which was distilled under reduced pressure to provide the product (28.8 g, 28percent) as a low melting white crystalline solid (b.p. 80-85 °C, 12 mm). LCMS: (M+H) +: not detected.
Reference: [1] Patent: WO2009/61879, 2009, A1, . Location in patent: Page/Page column 64
[2] Patent: WO2013/82388, 2013, A1, . Location in patent: Page/Page column 36; 70
  • 5
  • [ 767-79-3 ]
  • [ 96819-50-0 ]
  • [ 96819-51-1 ]
  • [ 6693-08-9 ]
Reference: [1] Journal of Fluorine Chemistry, 1989, vol. 45, p. 417 - 430
  • 6
  • [ 96819-51-1 ]
  • [ 6693-08-9 ]
Reference: [1] Journal of Fluorine Chemistry, 1989, vol. 45, p. 417 - 430
  • 7
  • [ 767-80-6 ]
  • [ 6693-08-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 5, p. 1669 - 1673
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