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[ CAS No. 1532533-67-7 ] {[proInfo.proName]}

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Chemical Structure| 1532533-67-7
Chemical Structure| 1532533-67-7
Structure of 1532533-67-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1532533-67-7 ]

CAS No. :1532533-67-7 MDL No. :MFCD28386165
Formula : C31H24F3N5O3 Boiling Point : -
Linear Structure Formula :- InChI Key :IUVCFHHAEHNCFT-INIZCTEOSA-N
M.W : 571.55 Pubchem ID :72950888
Synonyms :
TGR-1202;RP-5264

Calculated chemistry of [ 1532533-67-7 ]

Physicochemical Properties

Num. heavy atoms : 42
Num. arom. heavy atoms : 31
Fraction Csp3 : 0.16
Num. rotatable bonds : 6
Num. H-bond acceptors : 9.0
Num. H-bond donors : 1.0
Molar Refractivity : 153.18
TPSA : 109.06 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.64
Log Po/w (XLOGP3) : 5.83
Log Po/w (WLOGP) : 7.93
Log Po/w (MLOGP) : 4.4
Log Po/w (SILICOS-IT) : 6.67
Consensus Log Po/w : 5.89

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -7.21
Solubility : 0.0000355 mg/ml ; 0.0000000621 mol/l
Class : Poorly soluble
Log S (Ali) : -7.89
Solubility : 0.00000734 mg/ml ; 0.0000000128 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -11.32
Solubility : 0.0000000027 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.64

Safety of [ 1532533-67-7 ]

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 [ 1532533-67-7 ]

* 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 [ 1532533-67-7 ]
  • Downstream synthetic route of [ 1532533-67-7 ]

[ 1532533-67-7 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 1408087-64-8 ]
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YieldReaction ConditionsOperation in experiment
20%
Stage #1: With triphenylphosphine In tetrahydrofuran at 25 - 28℃; for 0.0833333 h; Reflux
Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 45℃; for 2 h;
(S)-2-(l-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-lH-pyrazolo[3,4-d]pyrimidin-l- yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one: To a solution of intermediate 13 (0.134 g, 0.494 mmol) in THF (2.0 ml), intermediate 5 (0.150 g, 0.494 mmol) and triphenylphosphine (0.194 g, 0.741 mml) were added and stirred at RT for 5 min. Diisopropylazodicarboxylate ( 0.15 ml, 0.749 mmol) was added heated to 45°C. After 2h, the reaction mixture was quenched with with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with ethyl acetate : petroleum ether to afford the title compound as an off-white solid (0.049 g, 20 percent). MP: 139- 142°C. Mass : 571.7 (M H-NMR (δ ppm, CDC13, 400 MHz): 8.24 (s, 1H), 7.85 (dd, J = 8.2,3.1 Hz, 1H), 7.50-7.29 (m, 5H), 7.14 (t, J = 8.4 Hz, 1H), 7.02 (m, 2H), 6.92 (d, J = 8.4 Hz, 1H), 6.11 (q, J = 7.1 Hz, 1H), 5.40 (s, 2H), 4.66 (quintet, J = 6.1 Hz, 1H), 2.00 (d, J = 7.1Hz, 3H), 1.42 (d, J = 6.1 Hz, 6H). Enantiomeric excess: 89.8percent as determined by HPLC on a chiralpak AD-H column, enriched in the fast eluting isomer (retention time = 10.64min.).
Reference: [1] Patent: WO2014/6572, 2014, A1, . Location in patent: Paragraph 127
  • 2
  • [ 1408087-64-8 ]
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  • [ 1532533-69-9 ]
YieldReaction ConditionsOperation in experiment
89.8 % ee With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 45℃; for 2 h; To a solution of intermediate 9 (0.134 g, 0.494 mmol) in THF (2.0 ml), intermediate 6 (0.150 g, 0.494 mmol) and triphenylphosphine (0.194 g, 0.741 mml) were added and stirred at RT for 5 min.
Diisopropylazodicarboxylate (0.15 ml, 0.749 mmol) was added heated to 45° C.
After 2 hours, the reaction mixture was quenched with water and extracted with ethyl acetate.
The organic layer was dried over sodium sulphate and concentrated under reduced pressure.
The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as an off-white solid (0.049 g, 20percent yield). MP: 139-142° C. Mass: 571.7 (M+).
Enantiomeric excess:
89.8percent as determined by HPLC on a chiralpak AD-H column, enriched in the fast eluting isomer (retention time=10.64 min.).
Reference: [1] Patent: US2015/290317, 2015, A1, . Location in patent: Paragraph 0280
  • 3
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Reference: [1] Patent: WO2014/6572, 2014, A1,
  • 4
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Reference: [1] Patent: WO2014/6572, 2014, A1,
  • 5
  • [ 1532533-31-5 ]
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Reference: [1] Patent: WO2014/6572, 2014, A1,
  • 6
  • [ 1300582-10-8 ]
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Reference: [1] Patent: WO2014/6572, 2014, A1,
  • 7
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Reference: [1] Patent: WO2014/6572, 2014, A1,
  • 8
  • [ 1300582-07-3 ]
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Reference: [1] Patent: WO2014/6572, 2014, A1,
  • 9
  • [ 2105-94-4 ]
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Reference: [1] Patent: WO2014/6572, 2014, A1,
  • 10
  • [ 1532533-34-8 ]
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Reference: [1] Patent: WO2014/6572, 2014, A1,
  • 11
  • [ 1532533-36-0 ]
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Reference: [1] Patent: WO2014/6572, 2014, A1,
  • 12
  • [ 459-60-9 ]
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Reference: [1] Patent: US2015/290317, 2015, A1,
[2] Patent: US2015/290317, 2015, A1,
  • 13
  • [ 1300582-07-3 ]
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Reference: [1] Patent: US2015/290317, 2015, A1,
[2] Patent: US2015/290317, 2015, A1,
  • 14
  • [ 331-25-9 ]
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Reference: [1] Patent: US2015/290317, 2015, A1,
[2] Patent: US2015/290317, 2015, A1,
  • 15
  • [ 1300582-08-4 ]
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Reference: [1] Patent: US2015/290317, 2015, A1,
  • 16
  • [ 1532533-31-5 ]
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  • [ 1532533-69-9 ]
Reference: [1] Patent: US2015/290317, 2015, A1,
  • 17
  • [ 1532533-32-6 ]
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  • [ 1532533-69-9 ]
Reference: [1] Patent: US2015/290317, 2015, A1,
  • 18
  • [ 1532533-34-8 ]
  • [ 1532533-67-7 ]
  • [ 1532533-69-9 ]
Reference: [1] Patent: US2015/290317, 2015, A1,
  • 19
  • [ 1532533-36-0 ]
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  • [ 1532533-69-9 ]
Reference: [1] Patent: US2015/290317, 2015, A1,
  • 20
  • [ 2105-94-4 ]
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Reference: [1] Patent: US2015/290317, 2015, A1,
  • 21
  • [ 202865-80-3 ]
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Reference: [1] Patent: US2015/290317, 2015, A1,
  • 22
  • [ 1300582-10-8 ]
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  • [ 1532533-69-9 ]
Reference: [1] Patent: US2015/290317, 2015, A1,
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