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[ CAS No. 912556-91-3 ] {[proInfo.proName]}

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Chemical Structure| 912556-91-3
Chemical Structure| 912556-91-3
Structure of 912556-91-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 912556-91-3 ]

CAS No. :912556-91-3 MDL No. :MFCD26383919
Formula : C18H16Cl2FN3O2 Boiling Point : -
Linear Structure Formula :C12H12N2O2ClNHC6H3ClF InChI Key :LYHIGZLXZKJTPS-UHFFFAOYSA-N
M.W : 396.24 Pubchem ID :50742265
Synonyms :

Calculated chemistry of [ 912556-91-3 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.22
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 101.44
TPSA : 56.27 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.41
Log Po/w (XLOGP3) : 5.03
Log Po/w (WLOGP) : 5.6
Log Po/w (MLOGP) : 3.51
Log Po/w (SILICOS-IT) : 5.02
Consensus Log Po/w : 4.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.46
Solubility : 0.00138 mg/ml ; 0.00000348 mol/l
Class : Moderately soluble
Log S (Ali) : -5.95
Solubility : 0.000442 mg/ml ; 0.00000112 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.42
Solubility : 0.00000152 mg/ml ; 0.0000000038 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.8

Safety of [ 912556-91-3 ]

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 [ 912556-91-3 ]

* 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 [ 912556-91-3 ]
  • Downstream synthetic route of [ 912556-91-3 ]

[ 912556-91-3 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 109-70-6 ]
  • [ 184475-71-6 ]
  • [ 912556-91-3 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 40℃; for 6 h; A suspension of 4-((3-chloro-4-fluorophenyl)amino)-7- methoxyquinazolin-6-ol (20.00 g), K2CO3(10.37 g), KI (1.04 g), l-bromo-3-chloropropane (7.50 mL) and DMF (150 mL) was stirred at 40 °C for 6 h. The reaction mixture was poured into water and filtered. The filter residue was purified by a silica gel column chromatography (eluting agent: EA) to give the title compound as pale yellow liquid (22.05 g, 89.00 percent). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 396.1 (M+l); ? NMR (400 MHz, CDC13) ?: 2.01 (m, 2H), 3.68 (t, J = 4.2 Hz, 2H), 4.00 (s, 3H), 4.10(t, J = 4.2 Hz, 2H), 6.80 (s, 1H), 7.16 (s, 1 H), 7.26 (s, 1H), 7.30 (s, 1 H), 7.47 (s, 1 H), 8.64 (s, 1H) ppm.
89% With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 40℃; for 6 h; A suspension of 4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-ol (20.00 g), K2CO3 (10.37 g), KI (1.04 g), 1-bromo-3-chloropropane (7.50 mL) and DMF (150 mL) was stirred at 40° C. for 6 h. The reaction mixture was poured into water and filtered. The filter residue was purified by a silica gel column chromatography (eluting agent: EA) to give the title compound as pale yellow liquid (22.05 g, 89.00percent). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 396.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.01 (m, 2H), 3.68 (t, J=4.2 Hz, 2H), 4.00 (s, 3H), 4.10 (t, J=4.2 Hz, 2H), 6.80 (s, 1H), 7.16 (s, 1H), 7.26 (s, 1H), 7.30 (s, 1H), 7.47 (s, 1H), 8.64 (s, 1H) ppm.
Ca. 330 mg With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 4 h; Heating The steps for the synthesis of intermediate compound 8: Refering to the formula IV, and according to the formula VI, compound 7 (478mg, 1.5mmol), 1-bromo-3-chloropropane (1.18g, 7.5mmol) and K2CO3 (1.05g, 7.5mmol) were added in into the flask prefilled with 3ml of DMF, heating it up to 90°C and keeping for 4 hours, and then cooling down to the room temperature. 15ml of water was added in, and the organic phases, extracted by ethyl acetate (20ml × 3), were combined. The combined organic phase was washed by water and saturated aqueous solution of Na2CO3 respectively. MgSO4, used as desiccant, was added. The solvent was removed by rotary evaporator after the desiccant was removed by filtration. Using silica gel column (gradient elution using petroleum ether containing 20v/vpercent-80v/vpercent ethyl acetate as eluent) to separate the residue, and about 330mg of product 8 was obtained.
Reference: [1] Patent: WO2013/71697, 2013, A1, . Location in patent: Paragraph 00197
[2] Patent: US2014/228361, 2014, A1, . Location in patent: Paragraph 0277-0278
[3] Patent: US2014/206664, 2014, A1, . Location in patent: Paragraph 0225; 0229
[4] Patent: EP2796451, 2014, A1, . Location in patent: Paragraph 0082
  • 2
  • [ 367-21-5 ]
  • [ 912556-91-3 ]
YieldReaction ConditionsOperation in experiment
89.1% With acetic acid In N,N-dimethyl-formamide at 135℃; N-dimethylformamidine, 0.72 g (6.15 mmol) of N '- [2-cyano-4,5-bis (2-methoxyethoxy) phenyl] ) Of 3-aminophenylacetylene and 8 mL of acetic acid were reacted in a 50 mL reaction flask at 125 ° C for 1 hour and cooled to room temperature.20 mL of ice water was added to the mixture, the pH was adjusted to 10 with aqueous ammonia, and the mixture was stirred for 1 hour, suction filtered and the filter cake washed with water until neutral.The filter cake was dried to obtain 2.15 g of erlotinib in a yield of 91.5percent.
88.3% at 130℃; for 0.5 h; General procedure: Followed the reference methods,1 3a-3d (5.0 mmol) was added to the mixture of acetic acid (5.0 mL) and R3 substituted aniline (6.0 mmol). The mixture was heated to 130 °C and stirred for 30 min. The mixture was then cooled to 25 °C. The acetic acid was evaporated. The mixture was quenched in ice-water (10 mL), and adjusted pH~9-10 with ammonia solution. Then it was stirred for 30 min in water. The precipitated product was filtered, and the filter cake was washed with water (3 × 10 mL) to give crude product. The final product was dried under vacuum to give 4a-4d, 5a-5d and 6a-6d (yield 74.9percent ~ 95.2percent).
Reference: [1] Patent: CN103539702, 2016, B, . Location in patent: Paragraph 0085-0087
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4309 - 4313
  • 3
  • [ 692059-41-9 ]
  • [ 367-21-5 ]
  • [ 912556-91-3 ]
Reference: [1] Molecules, 2007, vol. 12, # 3, p. 673 - 678
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5385 - 5388
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3637 - 3640
  • 4
  • [ 380844-22-4 ]
  • [ 912556-91-3 ]
Reference: [1] Molecules, 2007, vol. 12, # 3, p. 673 - 678
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3637 - 3640
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5385 - 5388
  • 5
  • [ 380844-26-8 ]
  • [ 912556-91-3 ]
Reference: [1] Molecules, 2007, vol. 12, # 3, p. 673 - 678
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3637 - 3640
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5385 - 5388
  • 6
  • [ 380844-24-6 ]
  • [ 912556-91-3 ]
Reference: [1] Molecules, 2007, vol. 12, # 3, p. 673 - 678
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3637 - 3640
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5385 - 5388
  • 7
  • [ 179688-53-0 ]
  • [ 912556-91-3 ]
Reference: [1] Patent: WO2013/71697, 2013, A1,
[2] Patent: US2014/206664, 2014, A1,
[3] Patent: US2014/228361, 2014, A1,
[4] Patent: EP2796451, 2014, A1,
  • 8
  • [ 230955-75-6 ]
  • [ 912556-91-3 ]
Reference: [1] Patent: WO2013/71697, 2013, A1,
[2] Patent: US2014/206664, 2014, A1,
[3] Patent: US2014/228361, 2014, A1,
[4] Patent: EP2796451, 2014, A1,
  • 9
  • [ 788136-89-0 ]
  • [ 912556-91-3 ]
Reference: [1] Patent: WO2013/71697, 2013, A1,
[2] Patent: US2014/206664, 2014, A1,
[3] Patent: US2014/228361, 2014, A1,
[4] Patent: EP2796451, 2014, A1,
  • 10
  • [ 13794-72-4 ]
  • [ 912556-91-3 ]
Reference: [1] Patent: WO2013/71697, 2013, A1,
[2] Patent: US2014/206664, 2014, A1,
[3] Patent: US2014/228361, 2014, A1,
[4] Patent: EP2796451, 2014, A1,
  • 11
  • [ 179688-52-9 ]
  • [ 912556-91-3 ]
Reference: [1] Patent: WO2013/71697, 2013, A1,
[2] Patent: US2014/206664, 2014, A1,
[3] Patent: US2014/228361, 2014, A1,
[4] Patent: EP2796451, 2014, A1,
  • 12
  • [ 6702-50-7 ]
  • [ 912556-91-3 ]
Reference: [1] Molecules, 2007, vol. 12, # 3, p. 673 - 678
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3637 - 3640
  • 13
  • [ 574738-93-5 ]
  • [ 912556-91-3 ]
Reference: [1] Molecules, 2007, vol. 12, # 3, p. 673 - 678
  • 14
  • [ 574738-93-5 ]
  • [ 912556-91-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3637 - 3640
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5385 - 5388
  • 15
  • [ 5653-40-7 ]
  • [ 912556-91-3 ]
Reference: [1] Patent: WO2013/71697, 2013, A1,
[2] Patent: US2014/228361, 2014, A1,
  • 16
  • [ 645-08-9 ]
  • [ 912556-91-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3637 - 3640
  • 17
  • [ 621-59-0 ]
  • [ 912556-91-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5385 - 5388
  • 18
  • [ 929683-54-5 ]
  • [ 912556-91-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5385 - 5388
  • 19
  • [ 1315512-62-9 ]
  • [ 912556-91-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4309 - 4313
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