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[ CAS No. 267243-28-7 ] {[proInfo.proName]}

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Chemical Structure| 267243-28-7
Chemical Structure| 267243-28-7
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Product Details of [ 267243-28-7 ]

CAS No. :267243-28-7 MDL No. :MFCD09837878
Formula : C24H25ClFN5O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 485.94 Pubchem ID :-
Synonyms :
CI-1033;PD-183805

Calculated chemistry of [ 267243-28-7 ]

Physicochemical Properties

Num. heavy atoms : 34
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.29
Num. rotatable bonds : 10
Num. H-bond acceptors : 7.0
Num. H-bond donors : 2.0
Molar Refractivity : 133.81
TPSA : 88.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.17
Log Po/w (XLOGP3) : 3.9
Log Po/w (WLOGP) : 4.24
Log Po/w (MLOGP) : 2.7
Log Po/w (SILICOS-IT) : 4.33
Consensus Log Po/w : 3.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.0
Solubility : 0.00488 mg/ml ; 0.00001 mol/l
Class : Moderately soluble
Log S (Ali) : -5.46
Solubility : 0.00169 mg/ml ; 0.00000348 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.22
Solubility : 0.00000295 mg/ml ; 0.0000000061 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.48

Safety of [ 267243-28-7 ]

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 [ 267243-28-7 ]

* 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.

  • Downstream synthetic route of [ 267243-28-7 ]

[ 267243-28-7 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 79-10-7 ]
  • [ 267243-68-5 ]
  • [ 267243-28-7 ]
YieldReaction ConditionsOperation in experiment
38% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl acetamide
  • 2
  • [ 4441-30-9 ]
  • [ 267243-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Na / tetrahydrofuran / 2 h / 20 °C 1.2: 58 percent / tetrahydrofuran 2.1: 78 percent / Fe; aq. HOAc / ethanol / 0.5 h / Heating 3.1: 38 percent / EDCI*HCl; Et3N / N,N-dimethyl-acetamide
  • 3
  • [ 367-21-5 ]
  • [ 267243-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 72 percent / CH2Cl2; propan-2-ol / 0.5 h / 20 °C 2.1: Na / tetrahydrofuran / 2 h / 20 °C 2.2: 58 percent / tetrahydrofuran 3.1: 78 percent / Fe; aq. HOAc / ethanol / 0.5 h / Heating 4.1: 38 percent / EDCI*HCl; Et3N / N,N-dimethyl-acetamide
  • 4
  • [ 162012-70-6 ]
  • [ 267243-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 72 percent / CH2Cl2; propan-2-ol / 0.5 h / 20 °C 2.1: Na / tetrahydrofuran / 2 h / 20 °C 2.2: 58 percent / tetrahydrofuran 3.1: 78 percent / Fe; aq. HOAc / ethanol / 0.5 h / Heating 4.1: 38 percent / EDCI*HCl; Et3N / N,N-dimethyl-acetamide
  • 5
  • [ 162012-67-1 ]
  • [ 267243-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Na / tetrahydrofuran / 2 h / 20 °C 1.2: 58 percent / tetrahydrofuran 2.1: 78 percent / Fe; aq. HOAc / ethanol / 0.5 h / Heating 3.1: 38 percent / EDCI*HCl; Et3N / N,N-dimethyl-acetamide
  • 6
  • [ 267243-64-1 ]
  • canertinib [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 78 percent / Fe; aq. HOAc / ethanol / 0.5 h / Heating 2: 38 percent / EDCI*HCl; Et3N / N,N-dimethyl-acetamide
  • 7
  • [ 736173-03-8 ]
  • [ 267243-28-7 ]
YieldReaction ConditionsOperation in experiment
92.9% With trifluoroacetic acid for 6h; Heating / reflux; 7.A Example 7; Preparation of N-[4-(3-chloro-4-fluoro-phenyl-amino)-7-(3-morpholin-4-yl-propoxy)-quinazolin-6-yl]-acrylamide [0141] Procedure A. N-[4-[(3-chloro-4-fluoro-phenyl)-(3,4-dimethoxy-benzyl)-amino]-7-(3-morpholin-4-yl-propoxy)-quinazolin-6-yl]-acrylamide (0.044 g, 0.069 mmol) was dissolved in trifluoroacetic acid (4 mL) then heated to reflux for 6 h. After cooling, the TFA was evaporated under reduced pressure and ethyl acetate was added. The resulting mixture was washed with dilute aqueous sodium bicarbonate. The organic layer was then washed with brine, dried over magnesium sulfate, filtered and evaporated under reduced pressure to give the crude product as a yellow foam. Chromatography on a BIOTAGE 12S cartridge eluted with 10% isopropanol in methylene chloride gave N-[4-(3-chloro-4-fluoro-phenyl-amino)-7-(3-morpholin-4-yl-propoxy)-quinazolin-6-yl]-acrylamide (0.031 g, 92.9%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.87 (s, 1H, CONH), 9.67 (s, 1H, NH), 8.93 (s, 1H, H-5), 8.60 (s, 1H, H-2), 8.20 (dd, J=7.05, 2.5 Hz, 1H, H-2'), 7.89-7.85 (m, 1H, H-6'), 7.49 (t, J=9.0 Hz, 1H, H-5'), 7.36 (s, 1H, H-8), 6.78 (dd, J=10.2, 17.1 Hz, 1H, CHCH2), 6.38 (dd, J=1.9, 17.1 Hz, 1H, CHCH2), 5.88 (dd, J=1.9, 10.2 Hz, 1H, CHCH2), 4.34 (t, J=6.3 Hz, 2H, CH2O), 3.66 (bs, 4H, -CH2NCH2-), 2.51 (bs, 4H, -CH2OCH2-), 2.08 (bt, J=6.6 Hz, 2H, CH2CH2CH2); MS (APCI+) m/z 486.2, 488.2 (M+1).
73.9% With methanesulfonic acid In tetrahydrofuran at 0 - 20℃; for 4 - 5h; 7.B [0142] Procedure B. A THF solution (50 mL approx. 0.72 M, 36.2 mmol) of N-[4-[(3-chloro-4-fluoro-phenyl)-(3,4-dimethoxy-benzyl)-amino]-7-(3-morpholin-4-yl-propoxy)-quinazolin-6 yl]-acrylamide was reduced in volume (to approx. 30 mL) under vacuum and cooled to 0-5° C. Methanesulfonic acid (46 mL, 710 mmol) was added, neat, while maintaining the temperature of the reaction mixture at <15° C. The reaction mixture was reduced in volume under vacuum at ambient temperature to approx. 60 mL and stirred at ambient temperature until all starting material was consumed (about 4-5 h). The crude product was obtained by quenching the mixture into NaOH/NaCl aq (300 mL, 3.0 M in NaOH) and filtering the resulting precipitate. The crude product was washed with water (4×25 mL) and dried overnight under a stream of N2. The crude product was recrystallized from acetone to yield N-[4-[(3-chloro-4-fluoro-phenylamino)-7-(3-morpholin-4-yl-propoxy)-quinazolin-6 yl]-acrylamide (13.00 g, 26.88 mmol, 73.9% from (3-chloro-4-fluoro-phenyl)-(3,4-dimethoxy-benzyl)-[7-(3-morpholin-4-yl-propoxy)-6-nitro-quinazolin-4-yl]-amine) as a slightly yellow solid.
YieldReaction ConditionsOperation in experiment
73% D Step D Step D N-[4-(3-Chloro-4-fluoro-phenylamino)-7-(3-morpholin-4-yl-propoxy)-quinazolin-6-yl]-acrylamide Isobutyl chloroformate (27.2 g, 0.20 mol) was added dropwise over 10 minutes to a solution of acrylic acid (14.40 g, 0.20 mol) and triethylamine (40.48 g, 0.40 mol) in THF (800 mL) stirred under nitrogen at 0° C. After a further 10 minutes, the white slurry was transferred to a-25° C. cooling bath and stirred under nitrogen for 20 minutes. 6-Amino-[(3-chloro4-fluorophenyl)amino]-7-[3-(4-morpholino)propoxy]quinazoline (43.19 g, 0.100 mol) in THF (500 mL) was added dropwise over 1.33 hours. The cooling bath was adjusted to-20° C., and after a further 2.33 hours, the reaction mixture was quenched by addition of water (100 mL) in one portion. After 20 minutes the reaction mixture was poured onto cracked ice (2 Kg), swirled, and gradually diluted with water (5 L). The mixture stood for 16 hours and was then Buchner filtered. The precipitate was rinsed with water (2*1 L), air dried for 18 hours, and then dried in a vacuum oven over P2O5 at 60° C. for 16 hours to give crude N-[4-[(3-chloro-4-fluorophenyl)amino]-7-[3-(4-morpholino)propoxy]quinazolin-6-yl]acrylamide (35.76 g, 73% uncorrected) as a greenish-yellow solid. The mother liquors precipitated further solid which was Buchner filtered, rinsed with water (1 L), and air dried for 14 hours to give further crude product (4.73 g, 10% uncorrected) as a greenish-yellow solid.
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