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[ CAS No. 147118-36-3 ] {[proInfo.proName]}

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Chemical Structure| 147118-36-3
Chemical Structure| 147118-36-3
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Product Details of [ 147118-36-3 ]

CAS No. :147118-36-3 MDL No. :MFCD08063917
Formula : C16H20FN3O3S Boiling Point : -
Linear Structure Formula :- InChI Key :MSDYDUNHTAYBHV-UHFFFAOYSA-N
M.W : 353.41 Pubchem ID :9819937
Synonyms :

Calculated chemistry of [ 147118-36-3 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.38
Num. rotatable bonds : 5
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 91.3
TPSA : 91.77 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 1.72
Log Po/w (WLOGP) : 3.64
Log Po/w (MLOGP) : 0.87
Log Po/w (SILICOS-IT) : 2.26
Consensus Log Po/w : 2.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.15
Solubility : 0.247 mg/ml ; 0.0007 mol/l
Class : Soluble
Log S (Ali) : -3.26
Solubility : 0.193 mg/ml ; 0.000545 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.1
Solubility : 0.00283 mg/ml ; 0.00000802 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.97

Safety of [ 147118-36-3 ]

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

Application In Synthesis of [ 147118-36-3 ]

* 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 [ 147118-36-3 ]
  • Downstream synthetic route of [ 147118-36-3 ]

[ 147118-36-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 147118-36-3 ]
  • [ 147118-39-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 2, p. 437 - 444
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  • [ 147118-36-3 ]
  • [ 289042-10-0 ]
Reference: [1] Patent: US6160115, 2000, A,
[2] Patent: WO2012/2741, 2012, A2,
[3] Organic Letters, 2018, vol. 20, # 11, p. 3286 - 3290
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  • [ 147118-36-3 ]
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YieldReaction ConditionsOperation in experiment
25.1 % With sodium iodide; sodium hydrogensulfite In trans-Decalin; ethyl acetate; mineral oil EXAMPLE 1
N-[5-(Diphenylphosphinoylmethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide
1.00 g (2.83 mmol) of [4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]methanol was initially charged in 5 ml of cis/trans-decalin and admixed with 204 mg (4.68 mmol) of sodium hydride (55 percent dispersion in mineral oil).
After 30 min at room temperature, 680 mg (2.93 mmol) of chlorodiphenylphosphine was added with vigorous stirring over a period of 6 min.
The mixture was admixed with 52.2 mg (0.35 mmol) of sodium iodide and heated at 184° to 186° C. for 2 h, 15 min.
After cooling to room temperature, 50 ml of 38 to 40 percent strength sodium bisulfite solution and 50 ml of ethyl acetate were added.
The organic phase was separated off and the aqueous phase was extracted with 50 ml of ethyl acetate.
The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure.
This gave 1.74 g of crude product which was purified by silica gel chromatography (mobile phase: n-hexane/ethyl acetate 1:2).
This gave 382.4 mg (25.1 percent) of N-[5-(diphenylphosphinoylmethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide in the form of a colorless solid.
The melting point was 180° to 185° C.
Other data concerning the product was:
Reference: [1] Patent: US6160115, 2000, A,
[2] Patent: US6160115, 2000, A,
[3] Patent: US6160115, 2000, A,
[4] Patent: US6160115, 2000, A,
[5] Patent: US6160115, 2000, A,
[6] Patent: US6160115, 2000, A,
[7] Patent: US6160115, 2000, A,
[8] Patent: US6160115, 2000, A,
[9] Patent: US6160115, 2000, A,
  • 4
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  • [ 147118-36-3 ]
  • [ 289042-10-0 ]
Reference: [1] Patent: US6160115, 2000, A,
  • 5
  • [ 147118-36-3 ]
  • [ 799842-07-2 ]
YieldReaction ConditionsOperation in experiment
99% With phosphorus tribromide In toluene; acetonitrile at 10 - 20℃; for 1 h; Inert atmosphere Reference Example 1: 5-Bromomethyl-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidine [Show Image] To the mixed solution of 5-hydroxymethyl-4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino] pyrimidine (15 g, 42.42 mmol) dissolved in anhydrous toluene (120 ml) and anhydrous acetonitrile (60 ml), phosphorus tribromide (5.4 g, 19.44 mmol) was slowly added dropwise at 10 to 20°C under nitrogen stream. After the reaction for 1 hour, saturated brine (100 ml) and distilled water (10 ml) were added to the reaction mixture, and the mixture was stirred for 10 minutes. After the aqueous layer was separated and discarded, the organic layer was sequentially washed with a saturated sodium hydrogencarbonate aqueous solution (50 ml) and distilled water (50 ml). The organic layer was dried with anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The obtained crude product was dispersed in hexane (100 ml), and the title compound (17.5 g, yield: 99percent) was obtained as a white solid by filtration. 1H-NMR(CDCl3): δ1.36H, d, J=6.6Hz), 3.48(1H, m), 3.51(3H, s), 3.56 (3H, s), 4.48(2H, s), 7.20 (2H, m), 7.80(2H, m)
90.6% With phosphorus tribromide In dichloromethane at 0 - 10℃; for 1 h; To a 1000 ml three-mouth bottle by adding 4 - (4 - fluorophenyl) -6 - isopropyl -2 - [(N - methyl - N - methanesulfonyl) amino] pyrimidine -5 - methanol (3) (70 g, 0.2 µM) and 420 ml dichloromethane, stirring under ice bath cooling to 0 - 10 °C, to the reaction system drop [...] phosphorus (59.0 g, 0 . 22 µM), stirring the reaction 1 h, TLC detection reaction is over. Add 250 ml water to stir liquid, organic layer respectively uses 200 ml 8percent sodium bicarbonate solution and 200 ml each wash once with purified water, collecting the organic phase and concentrated under reduced pressure to dry, the residue is added to 200 ml of petroleum ether beating at room temperature 2 h, filtering, the filter cake is dried to obtain the compound (4) a total of 75.4 g, yield 90.6percent. HPLC detection 98.9percent.
82% With phosphorus tribromide In dichloromethane at 20℃; for 1 h; Phosphorus tribromide (6.2 g, 0.023 mol) is added to a solution of the compound of formula (36) (16.2 g, 0.046 mol) in dichloromethane (180 ml). Stirring is carried out at room temperature for 1 hour and 150 ML of water are then added. The organic phase is separated off and dried (using NA2SO4). The salt mixture is filtered off and the filtrate is concentrated by evaporation. By that means, 15.7 G (82 percent) of the bromide (37) can be obtained in the form of a yellow powder. H NMR (300 MHz, CDCI3) : 1.36 (d, J = 6. 6 Hz, 6H); 3.40-3. 36 (m, 1H); 3.48 (s, 3H); 3.54 (s, 3H); 4.47 (s, 2H); 7.18 (dd, J = 8.8, 8.8 Hz, 2H); 7.78 (dd, J = 8.8, 5.3 Hz, 2H). 13C NMR (75 MHz, CDCI3) : 22.3, 28.0, 32.0, 33.5, 42. 8, 115. 9 (JF = 21.9 Hz), 119.6, 131.0 (JCF = 8.4 HZ), 133.8 (JCF = 3.5 Hz), 158.2, 163.8 (JCF = 250 Hz), 165.8, 177.6.
Reference: [1] Patent: EP2351762, 2011, A1, . Location in patent: Page/Page column 9
[2] Patent: CN108191772, 2018, A, . Location in patent: Paragraph 0019-0023
[3] Patent: WO2004/103977, 2004, A2, . Location in patent: Page 24
[4] Patent: US2005/124639, 2005, A1, . Location in patent: Page/Page column 7-8; 9
[5] Patent: WO2010/23678, 2010, A1, . Location in patent: Page/Page column 15
[6] Patent: WO2007/17117, 2007, A1, . Location in patent: Page/Page column 26
[7] Patent: WO2011/83495, 2011, A2, . Location in patent: Page/Page column 29-30
[8] Patent: WO2012/2741, 2012, A2,
[9] Asian Journal of Chemistry, 2017, vol. 29, # 5, p. 1018 - 1022
[10] Organic Letters, 2018, vol. 20, # 11, p. 3286 - 3290
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Reference: [1] Patent: WO2011/83495, 2011, A2,
[2] Patent: EP2351762, 2011, A1,
[3] Patent: WO2011/132172, 2011, A1,
[4] Patent: US2013/150579, 2013, A1,
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