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[ CAS No. 301693-50-5 ] {[proInfo.proName]}

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Chemical Structure| 301693-50-5
Chemical Structure| 301693-50-5
Structure of 301693-50-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 301693-50-5 ]

CAS No. :301693-50-5 MDL No. :MFCD22570932
Formula : C19H17FO2S Boiling Point : -
Linear Structure Formula :- InChI Key :OTXGJFNQTZTDPD-UHFFFAOYSA-N
M.W : 328.40 Pubchem ID :18385584
Synonyms :

Calculated chemistry of [ 301693-50-5 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.21
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 91.93
TPSA : 51.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.53
Log Po/w (XLOGP3) : 4.53
Log Po/w (WLOGP) : 5.21
Log Po/w (MLOGP) : 3.73
Log Po/w (SILICOS-IT) : 5.55
Consensus Log Po/w : 4.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.92
Solubility : 0.00397 mg/ml ; 0.0000121 mol/l
Class : Moderately soluble
Log S (Ali) : -5.34
Solubility : 0.00152 mg/ml ; 0.00000462 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.14
Solubility : 0.000024 mg/ml ; 0.0000000729 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.24

Safety of [ 301693-50-5 ]

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 [ 301693-50-5 ]

* 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 [ 301693-50-5 ]
  • Downstream synthetic route of [ 301693-50-5 ]

[ 301693-50-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 20769-85-1 ]
  • [ 301699-27-4 ]
  • [ 301693-50-5 ]
YieldReaction ConditionsOperation in experiment
86.8%
Stage #1: With sodium hydride In N,N-dimethyl acetamide at 0 - 5℃; for 1 h; Green chemistry
Stage #2: With 1,2,4-Triazole In N,N-dimethyl acetamide at 20℃; Green chemistry
A mixture of 2.60 g (10 mmol) of 2- (3-fluorophenyl) -1- (4-mercaptophenyl) ethanone and 20.8ml ofN, N-dimethylacetamide were stirred and cooled to 0 ° C. 60percent NaH 2.0 g (50 mmol) was added, and the mixture was kept at 0 to 5 ° C and stirred for 1.0 hour. 1.38g (20 mmol) of 1,2,4-triazole was mixed with 13.8 ml of N, N-dimethylacetamide, and 2.29 g (10 mmol) of 2-bromoisobutyryl bromide was added dropwise, and the mixture was stirred at about 30 minutes , The mixture was stirred for 2 hours, filtered and the insoluble material was filtered off. The filtrate was dropped into the reaction flask for about 1.0 hour. The mixture was stirred at room temperature overnight. After adding 2N hydrochloric acid (60 ml), the mixture was concentrated to near dryness, and 60 ml of water was added to the residue, filter, The filter cake was washed twice with water and recrystallized from ethanol to give 2.85 g of product, the yield was 86.8percent.
Reference: [1] Patent: CN106866558, 2017, A, . Location in patent: Paragraph 0102; 0103; 0104
[2] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 4, p. 1137 - 1142
  • 2
  • [ 301699-27-4 ]
  • [ 301693-50-5 ]
YieldReaction ConditionsOperation in experiment
85.9%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 5℃; for 1 h; Green chemistry
Stage #2: at 20℃; Green chemistry
A solution of 1.30 g (5 mmol) of 2- (3-fluorophenyl) -1- (4-mercaptophenyl) ethanone and 15 ml of tetrahydrofuran was stirred and cooled to 0 ° C. 60percent NaH 0.6 g (15 mmol) was added and the mixture was kept at 0 to 5 ° C and stirred for 1.0 hour. 1.23 g (5 mmol) of 1- (2-bromoisobutyryl) -3,5-dimethyl-1,2,4-triazole was dissolved in12.3 ml of tetrahydrofuran and dropped into the reaction flask for about 1.0 hour After mixing at room temperature overnight. 20 ml of 2N hydrochloric acid was added, concentrated under reduced pressure to remove tetrahydrofuran, and 30 ml of water was added to the residue, filter, The filter cake was washed twice with water and recrystallized from ethanol to give 1.41 g of product, yield 85.9percent.
Reference: [1] Patent: CN106866558, 2017, A, . Location in patent: Paragraph 0093; 0094; 0095
  • 3
  • [ 301699-27-4 ]
  • [ 301693-50-5 ]
YieldReaction ConditionsOperation in experiment
83.4%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 5℃; for 1 h; Green chemistry
Stage #2: at 20℃; Green chemistry
A solution of 1.30 g (5 mmol) of 2- (3-fluorophenyl) -1- (4-mercaptophenyl) ethanone and 15 ml of tetrahydrofuran was stirred and cooled to 0 ° C. 60percent NaH 0.6 g (15 mmol) was added and the mixture was kept at 0 to 5 ° C and stirred for 1.0 hour. A solution of 1.16 g (5 mmol) of 1- (2-bromoisobutyryl) -3-methyl-1,2,4-triazole was dissolved in 11.6 ml of tetrahydrofuran,And the mixture was dropped into the reaction flask for about 1.0 hour and stirred at room temperature overnight. 20 ml of 2N hydrochloric acid was added and concentrated under reduced pressure to remove tetrahydrofuran, and 30 ml of water was added to the residue, filter, The filter cake was washed twice with water and recrystallized from ethanol to give 1.37 g of product, yield 83.4percent
Reference: [1] Patent: CN106866558, 2017, A, . Location in patent: Paragraph 0090; 0091; 0092
  • 4
  • [ 301699-27-4 ]
  • [ 301693-50-5 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 5℃; for 1 h; Green chemistry
Stage #2: at 20℃; Green chemistry
A solution of 1.30 g (5 mmol) of 2- (3-fluorophenyl) -1- (4-mercaptophenyl) ethanone and 15 ml of tetrahydrofuran was stirred and cooled to 0 ° C. 60percent NaH 0.6 g (15 mmol) was added and the mixture was kept at 0 to 5 ° C and stirred for 1.0 hour. 1.26 g (5 mmol) of 1- (2-bromoisobutyryl) -3-chloro-1,2,4-triazole was dissolved in 12.6 ml of tetrahydrofuran and dropped into the reaction flask for about 1.0 hour, stirred at room temperature overnight. 20 ml of 2N hydrochloric acid was added, concentrated under reduced pressure to remove tetrahydrofuran, and 30 ml of water was added to the residue, filter, The filter cake was washed twice with water and recrystallized from ethanol to give 1.33 g of product, 81percent yield.
Reference: [1] Patent: CN106866558, 2017, A, . Location in patent: Paragraph 0096; 0097; 0098
  • 5
  • [ 301699-27-4 ]
  • [ 301693-50-5 ]
YieldReaction ConditionsOperation in experiment
82.2%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 5℃; for 1 h; Green chemistry
Stage #2: at 20℃; Green chemistry
A solution of 1.30 g (5 mmol) of 2- (3-fluorophenyl) -1- (4-mercaptophenyl) ethanone and 15 ml of tetrahydrofuran was stirred and cooled to 0 ° C. 60percent NaH 0.6 g (15 mmol) was added and the mixture was kept at 0 to 5 ° C and stirred for 1.0 hour. 1.09 g (5 mmol) of 1- (2-bromoisobutyryl) -1,2,4-triazole was dissolved in 10.9 ml of tetrahydrofuran and dripped into the reaction flask for about 1.0 hour. The mixture was stirred at room temperature overnight. 20 ml of 2N hydrochloric acid was added and concentrated under reduced pressure to remove tetrahydrofuran, and 30 ml of water was added to the residue, Filter, The filter cake was washed twice with water and recrystallized from ethanol to give 1.35 g of product, yield 82.2percent.
Reference: [1] Patent: CN106866558, 2017, A, . Location in patent: Paragraph 0083; 0084; 0085
  • 6
  • [ 301699-27-4 ]
  • [ 301693-50-5 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 5℃; for 1 h; Green chemistry
Stage #2: at 20℃; Green chemistry
A solution of 1.30 g (5 mmol) of 2- (3-fluorophenyl) -1- (4-mercaptophenyl) ethanone and 15 ml of tetrahydrofuran was stirred and cooled to 0 ° C. 60percent NaH 0.6 g (15 mmol) was added and the mixture was kept at 0 to 5 ° C and stirred for 1.0 hour. 0.868 g (5 mmol) of 1- (2-chloroisobutyryl) -1,2,4-triazole was dissolved in 8.7 ml of tetrahydrofuran and dropped into thereaction flask for about 1.0 hour. The mixture was stirred at room temperature overnight.20 ml of 2N hydrochloric acid was added and concentrated under reduced pressure to remove tetrahydrofuran, add waterto theresidue 30ml, filter, The filter cake was washed twice with water and recrystallized from ethanol to give 1.28 g of product, yield 78percent.
Reference: [1] Patent: CN106866558, 2017, A, . Location in patent: Paragraph 0087; 0088; 0089
  • 7
  • [ 116729-21-6 ]
  • [ 301699-27-4 ]
  • [ 301693-50-5 ]
YieldReaction ConditionsOperation in experiment
78% With sodium hexamethyldisilazane In tetrahydrofuran at -20℃; for 0.5 h; 26.5 g of Compound 1 and 10.4 g of Compound 2 were dissolved in tetrahydrofuran, cooled to -20 ° C,Add slowlySodium hexamethyldisilazide(2M, 57.2 mL). After the addition was completed,Stir for half an hourAdd water to quench the reaction,Add petroleum ether extraction,The combined organic phase,The organic phase was washed with 0.5M sodium hydroxide solution,Then dried,concentrate,Beating with methanol to give compound A,Yield 78percent.
Reference: [1] Patent: CN106977475, 2017, A, . Location in patent: Paragraph 0030; 031; 0035; 0036
  • 8
  • [ 55106-47-3 ]
  • [ 301699-27-4 ]
  • [ 301693-50-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 4, p. 1137 - 1142
[2] Patent: US6492416, 2002, B1,
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