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[ CAS No. 354-38-1 ] {[proInfo.proName]}

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Chemical Structure| 354-38-1
Chemical Structure| 354-38-1
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Product Details of [ 354-38-1 ]

CAS No. :354-38-1 MDL No. :MFCD00008008
Formula : C2H2F3NO Boiling Point : -
Linear Structure Formula :- InChI Key :NRKYWOKHZRQRJR-UHFFFAOYSA-N
M.W : 113.04 Pubchem ID :67717
Synonyms :

Calculated chemistry of [ 354-38-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 14.83
TPSA : 43.09 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) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.47
Log Po/w (XLOGP3) : 0.12
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : -0.14
Log Po/w (SILICOS-IT) : 0.69
Consensus Log Po/w : 0.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.55
Solubility : 31.8 mg/ml ; 0.282 mol/l
Class : Very soluble
Log S (Ali) : -0.58
Solubility : 29.7 mg/ml ; 0.263 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.3
Solubility : 56.9 mg/ml ; 0.504 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 354-38-1 ]

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

Application In Synthesis of [ 354-38-1 ]

* 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 [ 354-38-1 ]
  • Downstream synthetic route of [ 354-38-1 ]

[ 354-38-1 ] Synthesis Path-Upstream   1~76

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Reference: [1] Russian Journal of Organic Chemistry, 2004, vol. 40, # 4, p. 513 - 517
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Reference: [1] Patent: US5952375, 1999, A,
[2] Patent: US2004/53999, 2004, A1,
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YieldReaction ConditionsOperation in experiment
65% With NaH In tetrahydrofuran; ethyl acetate; mineral oil Example 6-B
Trifluoroacetamide (300 mg; 0.63 mmol) in THF (2 mL) at 0° C. was treated with NaH 60percent dispersion in mineral oil (50 mg; 0.63 mmol) followed by Mel (60 μL; 0.94 mmol) and the reaction was stirred at room temperature overnight THF was evaporated, the residue was diluted with water and extracted with CH2Cl2.
Combined organic layers were washed with saturated brine, dried over Na2SO4, concentrated and the crude was purified by flash chromatography over silica gel (eluding Hexanes/AcOEt 4:1 to 1:1) to give 200 mg (65percent) of N-methyltrifluoroacetamide.
Reference: [1] Patent: US2003/105094, 2003, A1,
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YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride; triethylamine In ethanol; ethyl acetate Example 5
Synthesis of Atropisomeric Trifluoroacetamide 3a
Atropisomer 2a as the sulfate salt (0.93 gm, 1.84 mmoles, 503.4 MW) was dissolved in 15 ml ethanol.
Triethylamine (1.8 ml, 13 mmoles) and ethyl trifluoroacetate (2.2 ml, 18 mmoles) were slowly added (FIG. 2a).
The mixture was stirred at room temperature under argon for 2.5 hours.
Volatiles were removed under vacuum and the resulting residue was dissolved in 300 ml ethyl acetate and washed with 2*50 ml of 5percent HCl.
The ethyl acetate fraction was dried over anhydrous Na2SO4, filtered and concentrated under vacuum to yield atropisomeric trifluoroacetamide 3a as an orange solid (0.92 gm, 100percent yield, 501.4 MW).
1H NMR (methanol-d4) δ8.35, 1H, d; 8.15, 1H, d; 7.80, 1H, s; 6.82, 1H, s; 6.65, 4H, m; 4.82, 2H, s.
Reference: [1] Patent: US6448407, 2002, B1,
[2] Journal of the American Chemical Society, 1943, vol. 65, p. 1459
[3] Journal of the American Chemical Society, 1943, vol. 65, p. 1459
[4] Journal of Organic Chemistry, 1959, vol. 24, p. 1256,1258
[5] Bulletin de la Classe des Sciences, Academie Royale de Belgique, 1922, vol. <5>8, p. 346[6] Bulletin des Societes Chimiques Belges, 1923, vol. 32, p. 104[7] Chem. Zentralbl., 1923, vol. 94, # I, p. 66
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[11] Journal of Organic Chemistry, 1988, vol. 53, # 11, p. 2573 - 2579
[12] Patent: US2003/143555, 2003, A1,
[13] Patent: US2003/158403, 2003, A1,
[14] Patent: US2013/150254, 2013, A1, . Location in patent: Page/Page column
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Reference: [1] Patent: US6288234, 2001, B1,
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  • 7
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Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 23, p. 6590 - 6594
  • 9
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  • 10
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Reference: [1] Patent: US2009/124692, 2009, A1,
  • 11
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Reference: [1] Canadian Journal of Chemistry, 1981, vol. 59, p. 431 - 450
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  • 13
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  • 14
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Reference: [1] Environmental Science and Technology, 1998, vol. 32, # 16, p. 2357 - 2370
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Reference: [1] Environmental Science and Technology, 1998, vol. 32, # 16, p. 2357 - 2370
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Reference: [1] Environmental Science and Technology, 1998, vol. 32, # 16, p. 2357 - 2370
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Reference: [1] Environmental Science and Technology, 1998, vol. 32, # 16, p. 2357 - 2370
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Reference: [1] Environmental Science and Technology, 1998, vol. 32, # 16, p. 2357 - 2370
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YieldReaction ConditionsOperation in experiment
40% With Lawessons reagent In tetrahydrofuranReflux A solution of 2,2,2-trifluoroacetamide (14.24 g, 1 eq.) and Lawesson's reagent (30.6 g, 0.6 eq.) in THF (120 mL) was stirred at reflux for 18 hrs. The mixture was cooled, ethyl bromopyruvate (16 mL, 1 eq.) was added and the reaction refluxed for weekend. The reaction was cooled, evaporated in vacuum, and the resulting crude material extracted with dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give an orange oil. The oil was purified by chromatography on a silica gel (petroleum ether/dichloromethane) to yield compound 251 in 40percent yield. 1H NMR- 161 -SDI-18153v2 (DMSO-J6, 400 MHz): δ (ppm) 1.32 (t, J= 7.10 Hz, 3H), 4.34 (q, J= 7.10 Hz, 2H), 8.9 (s,IH); 119T NMR (DMSO-J6, 376 MHz): δ (ppm) -60.29 (s, 3F); MS (ESI, EI+): m/z = 225.9(MH+).
32%
Stage #1: With Lawessons reagent In tetrahydrofuran for 18 h; Reflux
Stage #2: for 18 h; Reflux
A mixture of 2,2,2-trifluoroacetamide (7.12g, 63 mmol) and Lawesson's reagent (15.3 g, 37.8 mmol) in THF (60 mL) was heated at reflux for 18 hours. The reaction was then cooled down to RT and treated with ethyl bromopyruvate (8.0 mL, 63 mmol). The reaction was stirred at reflux for an additional 18 hours, then concentrated under vacuum and diluted with ethyl acetate. This mixture was washed with water (IX) and brine (IX), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (8X1 1 cm, toluene, then second time with 120g silica gel, hexane/ethyl acetate) to give the title material (4.47g, 32percent) as a pale yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.37 (s, 1H), 4.45 (q, J= 7.0 Hz, 2H), 1.41 (t, J= 7.0 Hz, 1H).
Reference: [1] Patent: WO2011/17389, 2011, A1, . Location in patent: Page/Page column 161-162
[2] Patent: WO2013/163279, 2013, A1, . Location in patent: Paragraph 00141
[3] Patent: US2015/18328, 2015, A1, . Location in patent: Paragraph 1206
[4] Patent: WO2015/3640, 2015, A1, . Location in patent: Page/Page column 265
  • 76
  • [ 19172-47-5 ]
  • [ 354-38-1 ]
  • [ 70-23-5 ]
  • [ 133046-46-5 ]
YieldReaction ConditionsOperation in experiment
21%
Stage #1: for 18 h; Heating / reflux
Stage #2: for 18 h; Heating / reflux
A solution of 2,2, 2-trifluoroacetamide (7.12 g, 63 mmol) and Lawesson's Reagent (15.3 g, 37.8 mmol) in THF (anhydrous, 60 ml) was stirred at reflux for 18 h. The reaction mixture was cooled, then ethyl bromopyruvate (8 ml, 63 mmol) added, and refluxed for 18 h. The reaction was cooled, evaporated in vacuo, and the resulting crude material extracted into ethyl acetate and washed with water. The organic fraction was dried over MgSO4, and condensed to givea yellow/orange oil. The residue was purified by flash column chromatography on silica eluting with 15 percent ethyl acetate in hexane to provide the title compound as a clear oil (3 g, 21 percent). 1H NMR (400MHz,CDCI3)8 8.39(1H, s), 4.47 (2H, q, J7. 1), 1.42 (3H, t, J7.2).
Reference: [1] Patent: US2013/289238, 2013, A1, . Location in patent: Page/Page column
[2] Patent: WO2005/49613, 2005, A1, . Location in patent: Page/Page column 50
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