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[ CAS No. 152459-94-4 ]

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Chemical Structure| 152459-94-4
Chemical Structure| 152459-94-4
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Product Details of [ 152459-94-4 ]

CAS No. :152459-94-4 MDL No. :MFCD00945675
Formula : C23H19N5O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :381.43 g/mol Pubchem ID :9864718
Synonyms :

1. CGP-53716

Safety of [ 152459-94-4 ]

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 [ 152459-94-4 ]

  • Downstream synthetic route of [ 152459-94-4 ]

[ 152459-94-4 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 98-88-4 ]
  • [ 152460-10-1 ]
  • [ 152459-94-4 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine; In tetrahydrofuran; at 0 - 25℃; for 3h; will1c (7.5g, 0.027mol, Suzhou Xinkai Bio-pharmaceutical Technology Co., Ltd.) Into a 250mL three-necked flask, add tetrahydrofuran (135mL) and triethylamine (7.53mL), stirring to reduce the internal temperature 0 ~ 3 C, 1b ( 5.75g, 0.041mol) in tetrahydrofuran (57mL) solution, the internal temperature is controlled below 5 C, after the drop is complete, the temperature is raised to 20 ~ 25 C, the reaction is incubated for 3 hours, stirringPurified water (415 mL) was added thereto, lowered to room temperature, filtered, and washed with purified water (30 mL×2) and vacuum dried at 75 to 80 C. for 2 hours to obtain N-[4-methyl-3-[[4] as a yellow solid. -(3-pyridyl)-2-pyrimidinyl]amino]phenyl]benzamide (1d) 10 g, yield 97%.
With triethylamine; In dichloromethane; at 0℃; for 4h; General procedure: The imatinib analogs 3,4-R1,R2-N-(4-methyl-3(4-(pyridine-3-yl)pyrimidin-2-ylamino)phenyl)benzamide (R1 = R2 = H (1); R1 = H, R2 = SCH3 (2); R1 = NO2, R2 = H (3); R1 = NH2, R2 = H (4); R1 = R2 = NO (5)) and N-(4-methyl-3-(4-(pyridin-3-yl) pyrimidin-2-ylamino)phenyl)picolinamide (6) was synthesized following a modified procedure described in the literature16 as shown in Scheme 1. Briefly, an excess amount of benzoyl chloride compound 1b, 2b, 3b, 4b, 5b or 6b was added to a suspension of 6-methyl-N-(4-(pyridin-3-yl)pyrimidin-2-yl) benzene-1,3-diamine (0.5 g, 2 mmol) in dichloromethane (10 mL) containing TEA (0.58 mL, 4 mmol), and the mixture was reacted at 0 C for 4 h, and TLC of reaction mass indicated the absence of starting compound. The solution was then filtered and washed with dichloromethane, the excess dichloromethane was removed in vacuo, and the residue was purified by recrystallization from ethanol.
  • 2
  • [ 152459-94-4 ]
  • N-{4-Methyl-3-[4-(1-oxy-pyridin-3-yl)-pyrimidin-2-ylamino]-phenyl}-benzamide [ No CAS ]
  • 4
  • [ 55314-16-4 ]
  • [ 152459-94-4 ]
  • 6
  • 1-(2-methyl-5-nitrophenyl)guanidine nitrate [ No CAS ]
  • [ 152459-94-4 ]
YieldReaction ConditionsOperation in experiment
or 3wherein the compound is selected from the group comprising: ... 2-Methoxy-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide; 2-Methoxy-N-[3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide; 4-Methyl-N-[3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide; 4-Methyl-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide; N-[4-Methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide; 1(3,5-Diacetyl-phenyl)-3-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-pheny]-urea; 1-{3,5-Bis-(amidinohydrazone)-phenyl}-3-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-urea; N-[4-Methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-nicotinamide; ...
  • 9
  • [ 1451042-84-4 ]
  • [ 1692-25-7 ]
  • [ 152459-94-4 ]
YieldReaction ConditionsOperation in experiment
49% N-[3-(4-Oxopyrimidin-2-ylamino)-4-methylphenyl]-benzamide (0.36 g, 1.12 mmol), PyBrOP (0.55 g, 1.18 mmol) and 0.47 ml of triethylamine in anhydrous dioxane (15 ml) was stirred at 45 C under argon for 0.5 h. To the solution 3-pyridinylboronic acid (145 mg, 1.18 mmol) and catalyst PdCl2(PPh3)2 (39.4 mg, 5 -mol%) was sequentially added under argon. After stirring for 0.5 h at room temperature deaerated aqueous solution of 1 M Na2CO3 (3.4 ml, 3.4 mmol) was added by syringe and stirring was continued for 24 h at 100 C under argon. Reaction mixture diluted with ethyl acetate (30 ml) and brine (5 % solution). Organic phase was separated, washed with brine (15 ml) and filtered through celite and dried. After evaporation of solvent the residue was crystallized from ethanol to obtain 0.21 g (49%) of amorphous substance with mp.178-182 C. [BioMed.Chem.Lett, 201 1 , 21 , 6964 m.p. 190-191 C] 1 H NMR (DMSO-Ok): 2.22 (s,3H), 7.43 (d J= 5.2 Hz, 1 H), 7.52 (m, 5H), 7.95 (m, 2H), 8.09 (d J= 1.9 Hz, 1 H), 8.48 (dt J= 8.1 ; 1.8 Hz, 1 H), 8.51 (d J= 5.2 Hz, 1 H), 8.68 (dd J= 4.8; 1.8 Hz, 1 H), 8.97 (s, 1 H), 9.29 (d J= 1.9 Hz, 1 H), 10.20 (s, 1 H).
  • 10
  • [ 1025717-41-2 ]
  • [ 152459-94-4 ]
  • 11
  • [ 99-55-8 ]
  • [ 152459-94-4 ]
  • 12
  • [ 1451042-77-5 ]
  • [ 152459-94-4 ]
  • 13
  • [ 152459-94-4 ]
  • C23H19N5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 - 20℃; for 72h; Synthesis of (1e) 1d (10 g, 0.027 mol) was put into a 500 mL three-necked flask, methylene chloride (350 mL) was added, and m-chloroperbenzoic acid (11.2 g, 0.065 mol, Sigma-Aldrich Sigmamae) was added at -20C. (Drich Shanghai Trading Co., Ltd.), raised to room temperature, reacted for 72 hours, filtered, and the filtrate was concentrated to dryness under reduced pressure, and purified by silica gel column chromatography with eluent: methanol: dichloromethane=1:20 (volume ratio, v /v) gives N-[4-methyl-3-[[4-(1-oxo-3-pyridyl)-3-oxo-2-pyrimidinyl]amino]phenyl]benzene as a yellow solid Amide (1e) 5.47 g, yield 49%.
  • 14
  • [ 65-85-0 ]
  • [ 152460-10-1 ]
  • [ 152459-94-4 ]
YieldReaction ConditionsOperation in experiment
90% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 20℃; for 1h; General procedure: The final target compounds were synthesized from 6-methyl-N-(4-(pyridin-3-yl) pyrimidin-2-yl) benzene-1,3-diamine 8(2 mmol), DMF (10 mL), and DIPEA (4 mmol) followed by substituted aromatic acid (2 mmol) was added and stirred at room temperature for 1 h. After completion of the reaction mixture was poured into ice-cold water. The obtained yellow precipitate washed with water and dried to get target titled product pyrimidine scaffold benzamide derivatives (9 a-k).
  • 15
  • [ 55314-16-4 ]
  • [ 152459-94-4 ]
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