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[ CAS No. 199475-45-1 ] {[proInfo.proName]}

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Chemical Structure| 199475-45-1
Chemical Structure| 199475-45-1
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Product Details of [ 199475-45-1 ]

CAS No. :199475-45-1 MDL No. :MFCD01312116
Formula : C7H4BrNOS Boiling Point : -
Linear Structure Formula :- InChI Key :BNWQDLHPYANRAV-UHFFFAOYSA-N
M.W : 230.08 Pubchem ID :2801273
Synonyms :

Calculated chemistry of [ 199475-45-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.15
TPSA : 61.1 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) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 2.35
Log Po/w (MLOGP) : 2.07
Log Po/w (SILICOS-IT) : 3.97
Consensus Log Po/w : 2.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.42
Solubility : 0.0884 mg/ml ; 0.000384 mol/l
Class : Soluble
Log S (Ali) : -3.38
Solubility : 0.0967 mg/ml ; 0.00042 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.74
Solubility : 0.0423 mg/ml ; 0.000184 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.12

Safety of [ 199475-45-1 ]

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 [ 199475-45-1 ]

* 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 [ 199475-45-1 ]
  • Downstream synthetic route of [ 199475-45-1 ]

[ 199475-45-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 32315-10-9 ]
  • [ 93933-49-4 ]
  • [ 199475-45-1 ]
YieldReaction ConditionsOperation in experiment
15% for 18 h; Reflux To a solution of2-amino-4-bromobenzenethiol (544 mg,2.67 mmol)in acetic acid (26.7mL)was added triphosgene (530 mg,1.79 mmol). The mixture was heated at reflux for 18 h.After cooling to room temperature,the solution was partially concentrated under reducedpressure,water was added,and the resulting precipitate was removed via filtration,and washed with aqueous NaOH (1.0 M). The filtrate was acidified with HCl (2 N)to pH 2,and placed in arefrigerator for 12 h. The resulting precipitate was filtered,washed with water,and dried underreduced pressure to give the title compound (94 mg,15percent)as a while powder that required nofurther purification. 1H NMR (400 MHz,DMSO-d6)8 12.07 (s,1H),7.55 (d,J = 8.4 Hz,1H),5 7.30 (d,J = 8.0 Hz,1H),7.24 (s,1H).
20 g at 0℃; for 18 h; Reflux Zn (70 g, 1077 mmol) was added to a solution of B (28 g, 120 mmol) in AcOH (500 ml). Reaction mixture was stirred at 65°C for 15 h under nitrogen to give C, monitored by TLC. The mixture was cooled to room temperature, and triphosgene (25 g, 84 mmol) added slowly at 0°C. Mixture was refluxed for 18 h, monitored by TLC. Solution was then concentrated and hydrolyzed with water. Yellow solid was collected to give D (20 g, 73percent, over two steps).
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 24, p. 10151 - 10171
[2] Patent: WO2017/205536, 2017, A2, . Location in patent: Page/Page column 83; 84
[3] Patent: WO2014/190199, 2014, A1, . Location in patent: Paragraph 00285
  • 2
  • [ 32315-10-9 ]
  • [ 76209-02-4 ]
  • [ 199475-45-1 ]
Reference: [1] Synthesis, 2011, # 3, p. 480 - 484
  • 3
  • [ 3460-18-2 ]
  • [ 199475-45-1 ]
Reference: [1] Patent: WO2014/190199, 2014, A1,
  • 4
  • [ 76209-02-4 ]
  • [ 199475-45-1 ]
Reference: [1] Patent: WO2014/190199, 2014, A1,
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