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[ CAS No. 1202757-89-8 ] {[proInfo.proName]}

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Chemical Structure| 1202757-89-8
Chemical Structure| 1202757-89-8
Structure of 1202757-89-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1202757-89-8 ]

CAS No. :1202757-89-8 MDL No. :
Formula : C22H22FN5O3 Boiling Point : -
Linear Structure Formula :- InChI Key :KXBDTLQSDKGAEB-UHFFFAOYSA-N
M.W : 423.44 Pubchem ID :59174488
Synonyms :

Calculated chemistry of [ 1202757-89-8 ]

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.14
Num. rotatable bonds : 11
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 116.91
TPSA : 97.4 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.55
Log Po/w (XLOGP3) : 3.64
Log Po/w (WLOGP) : 4.48
Log Po/w (MLOGP) : 2.18
Log Po/w (SILICOS-IT) : 3.2
Consensus Log Po/w : 3.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.46
Solubility : 0.0146 mg/ml ; 0.0000345 mol/l
Class : Moderately soluble
Log S (Ali) : -5.37
Solubility : 0.00179 mg/ml ; 0.00000423 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.1
Solubility : 0.0000034 mg/ml ; 0.000000008 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.44

Safety of [ 1202757-89-8 ]

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 [ 1202757-89-8 ]

* 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 [ 1202757-89-8 ]
  • Downstream synthetic route of [ 1202757-89-8 ]

[ 1202757-89-8 ] Synthesis Path-Upstream   1~9

  • 1
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YieldReaction ConditionsOperation in experiment
80%
Stage #1: at -10℃;
Stage #2: With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 0.166667 h;
A solution of 6 (309 mg, 0.84 mmol) in THF (10 mL) was cooled in a water/ice- MeOH bath (-10 0C). To this was added 7 (71 μL, 0.88 mmoL), stirred for 10 min, then added Hunig's base (145uL, 0.88mmoL), and stirred for 10 min. Partitioned between water/brine (10 <n="194"/>niL), agitated and separated the layers. Dried organic phase over sodium sulfate. The solvent was removed via rotary evaporation and triturated with diethyl ether to afford after filtration 285 mg (80percent) of an off-white solid. LC/MS (RT = 2.79/(M + H)) 424.2.
0.28 g at -30℃; In a 50 mL 3-neck RBF equipped with a magnetic stirrer, calcium chloride guard tube and thermo pocket was charged N4-(3-aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine (0.40 g) in dry DCM (10 mL) and was cooled to −30° C. An acryloyl chloride solution in DCM (0.107 g in 5.0 mL DCM) was added slowly and the reaction mixture was stirred at −30° C. for approx. 40 minutes. The reaction was monitored on TLC using chloroform:methanol (9.6:0.4) as mobile phase. The reaction mixture was poured into water (100 mL) and basified using sodium bicarbonate. The reaction mixture was extracted with MDC (2×25 mL) and the combined organic layer was washed with 50 mL brine solution. The organic layer was dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. Obtained solid was purified by triturating with diethyl ether (2×10 mL) and dried under vacuum to give 0.28 g N-(3-((5-fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)acrylamide.
0.28 g at -30℃; for 0.666667 h; In a 50 mL 3-neck RBF equipped with a magnetic stirrer, calcium chloride guard tube and thermo pocket was charged N4-(3-aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxyl)phenyl)pyrimidine-2,4-diamine (0.40 g) in dry DCM (10 mL) and was cooled to -30° C.
An acryloyl chloride solution in DCM (0.107 g in 5.0 mL DCM) was added slowly and the reaction mixture was stirred at -30° C. for approx. 40 minutes.
The reaction was monitored on TLC using chloroform:methanol (9.6:0.4) as mobile phase.
The reaction mixture was poured into water (100 mL) and basified using sodium bicarbonate.
The reaction mixture was extracted with MDC (2*25 mL) and the combined organic layer was washed with 50 mL brine solution.
The organic layer was dried over sodium sulfate and concentrated completely under reduce pressure at 40° C.
Obtained solid was purified by triturating with diethyl ether (2*mL) and dried under vacuum to give 0.28 g N-(3-((5-fluoro-2-((4-(2-methoxyethoxyl)phenyl)amino)pyrimidin-4-yl)amino)phenyl)acrylamide.
Reference: [1] Patent: WO2009/158571, 2009, A1, . Location in patent: Page/Page column 190; 192
[2] Patent: US2014/179720, 2014, A1, . Location in patent: Paragraph 0380; 0383
[3] Patent: US2015/174128, 2015, A1, . Location in patent: Paragraph 0629
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Reference: [1] Patent: US2014/179720, 2014, A1,
[2] Patent: US2015/174128, 2015, A1,
[3] Patent: US2015/174128, 2015, A1,
[4] Patent: US2015/174128, 2015, A1,
[5] Patent: WO2009/158571, 2009, A1,
  • 3
  • [ 68621-88-5 ]
  • [ 1202757-89-8 ]
Reference: [1] Patent: US2015/174128, 2015, A1,
[2] Patent: US2015/174128, 2015, A1,
[3] Patent: US2015/174128, 2015, A1,
[4] Patent: WO2009/158571, 2009, A1,
  • 4
  • [ 1202759-90-7 ]
  • [ 1202757-89-8 ]
Reference: [1] Patent: US2014/179720, 2014, A1,
[2] Patent: US2015/174128, 2015, A1,
[3] Patent: WO2009/158571, 2009, A1,
  • 5
  • [ 33311-29-4 ]
  • [ 1202757-89-8 ]
Reference: [1] Patent: US2014/179720, 2014, A1,
[2] Patent: US2015/174128, 2015, A1,
  • 6
  • [ 99-09-2 ]
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Reference: [1] Patent: US2014/179720, 2014, A1,
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  • [ 18437-64-4 ]
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Reference: [1] Patent: US2014/179720, 2014, A1,
  • 8
  • [ 528882-15-7 ]
  • [ 1202757-89-8 ]
Reference: [1] Patent: US2014/179720, 2014, A1,
  • 9
  • [ 528882-16-8 ]
  • [ 1202757-89-8 ]
Reference: [1] Patent: US2014/179720, 2014, A1,
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N-(3-((5-Fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)acrylamide benzenesulfonate

Reason: Free-salt