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[ CAS No. 349-49-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 349-49-5
Chemical Structure| 349-49-5
Chemical Structure| 349-49-5
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Product Details of [ 349-49-5 ]

CAS No. :349-49-5 MDL No. :MFCD00832759
Formula : C4H3F3N2S Boiling Point : -
Linear Structure Formula :- InChI Key :OVMGTNMCYLZGLS-UHFFFAOYSA-N
M.W : 168.14 Pubchem ID :1201417
Synonyms :

Calculated chemistry of [ 349-49-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.52
TPSA : 67.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 2.9
Log Po/w (MLOGP) : 0.67
Log Po/w (SILICOS-IT) : 2.54
Consensus Log Po/w : 1.79

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.15
Solubility : 1.19 mg/ml ; 0.00707 mol/l
Class : Soluble
Log S (Ali) : -2.55
Solubility : 0.475 mg/ml ; 0.00282 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.81
Solubility : 2.57 mg/ml ; 0.0153 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 349-49-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 349-49-5 ]

* 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 [ 349-49-5 ]
  • Downstream synthetic route of [ 349-49-5 ]

[ 349-49-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 431-35-6 ]
  • [ 17356-08-0 ]
  • [ 349-49-5 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: at 50℃; for 2 h;
Preparation 214-Trifluoromethyl-thiazole-2-ylamineAdd thiourea (4.0 g, 52.3 mmol) and 3-bromo-l,l,l-trifluoropropan-2-one (5.5 mL, 10 g, 52.3 mmol) to ethanol (100 mL) and heat at 50 0C for 2 h. Cool to room temperature and concentrate to dryness. Dissolve the residue in water and adjust the pH to >12 with 2 M NaOH. Extract with diethyl ether (4*). Dry the combined organic extracts with sodium sulfate, filter, and concentrate under vacuum. Purify the resulting material by silica gel chromatography (CH2Cl2) to obtain the title compound (6.9 g, 79percent). ES/MS m/z 169 (M+ 1)+.
Reference: [1] Patent: WO2008/36579, 2008, A1, . Location in patent: Page/Page column 43
[2] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 907 - 911
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1051 - 1053
[4] Journal of Organic Chemistry, 1955, vol. 20, p. 499,505
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 2335 - 2339
[6] Patent: US2009/286811, 2009, A1, . Location in patent: Page/Page column 20
[7] Patent: US2003/236287, 2003, A1, . Location in patent: Page 35
[8] Patent: WO2012/89607, 2012, A1, . Location in patent: Page/Page column 38-39
  • 2
  • [ 533887-24-0 ]
  • [ 349-49-5 ]
YieldReaction ConditionsOperation in experiment
30% With thiourea In N,N-dimethyl-formamide at 90℃; Step 5: A solution consisting of 1.0 g of 2-(phenylsulfonyl)-3- (trifluoromethyl)oxirane and 2 equiv of thiourea in 4 mL of dimethylformamide was heated overnight at 90 0C. After cooling, 40 mL Of CH2Cl2 was added and the dark solution washed successively with water and brine. Charcoal was then added and after filtration and evaporation of the solvent, the residue was chromatographed on silica gel to get 4-(trifluoromethyl)thiazol-2-amine (200 mg, yield 30percent).
Reference: [1] Patent: WO2010/30811, 2010, A2, . Location in patent: Page/Page column 92
  • 3
  • [ 533887-24-0 ]
  • [ 17356-08-0 ]
  • [ 349-49-5 ]
YieldReaction ConditionsOperation in experiment
30% at 90℃; Step 5: A solution consisting of 1.0 g of 2-(phenylsulfonyl)-3- (trifluoromethyl)oxirane and 2 equiv of thiourea in 4 mL of dimethylformamide was heated overnight at 90°C. After cooling, 40 mL of CH2Cl2 was added and the dark solution washed successively with water and brine. Charcoal was then added and after filtration and evaporation of the solvent, the residue was chromatographed on silica gel to get 4-(trifiuoromethyl)thiazol-2-amine (200 mg, yield 30percent).
Reference: [1] Patent: WO2010/123997, 2010, A1, . Location in patent: Page/Page column 65; 88
  • 4
  • [ 431-37-8 ]
  • [ 17356-08-0 ]
  • [ 349-49-5 ]
Reference: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 499,505
[2] Patent: WO2005/110980, 2005, A2, . Location in patent: Page/Page column 92
  • 5
  • [ 17356-08-0 ]
  • [ 169260-95-1 ]
  • [ 349-49-5 ]
Reference: [1] Journal of Fluorine Chemistry, 1995, vol. 73, # 1, p. 83 - 86
  • 6
  • [ 1349091-16-2 ]
  • [ 17356-08-0 ]
  • [ 349-49-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 24, p. 8670 - 8680
  • 7
  • [ 349-49-5 ]
  • [ 136411-21-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 1017 - 1024
[2] Patent: WO2005/110980, 2005, A2, . Location in patent: Page/Page column 92-93
[3] Patent: WO2011/143466, 2011, A1, . Location in patent: Page/Page column 59
  • 8
  • [ 349-49-5 ]
  • [ 682342-65-0 ]
Reference: [1] Patent: US2004/82629, 2004, A1, . Location in patent: Page 4
  • 9
  • [ 349-49-5 ]
  • [ 41731-39-9 ]
YieldReaction ConditionsOperation in experiment
24%
Stage #1: With hydrogen bromide In water
Stage #2: With sodium nitrite In water at 0℃; for 1 h;
2-Amino-4-(trifluoromethyl)thiazole (Wako Pure Chemical Industries, Ltd., 500 mg) was added to 48percent aqueous hydrogen bromide (6 ml) and, under ice-cooling, sodium nitrite (266 mg) dissolved in water (1 ml) was added dropwise thereto. The mixture was stirred at 0°C for 1 hr. A sodium hydrogen sulfite aqueous solution, and then an aqueous sodium hydroxide solution were added, and the mixture was extracted with diethyl ether. The organic layer was dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate-hexane (1:9)) to give 2-bromo-4-(trifluoromethyl)thiazole (167 mg, yield 24percent). 1H-NMR(300MHz,DMSO-d6)δ(ppm): 8.55(1H,s). By a similar operation as in Starting Material Synthetic Example 17, 1-[4-(trifluoromethyl)-1,3-thiazol-2-yl]piperazine hydrochloride (194 mg, yield 53percent) was obtained from 2-bromo-4-(trifluoromethyl)thiazole (309 mg) and 1-(tert-butoxycarbonyl)piperazine (300 mg). 1H-NMR(300MHz,DMSO-d6)δ(PPM): 3.19-3.24(4H,m), 3.66-3.75(4H,m), 7.68(1H,s), 9.57(2H,brs).
Reference: [1] Patent: EP1714961, 2006, A1, . Location in patent: Page/Page column 17
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