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[ CAS No. 870221-17-3 ] {[proInfo.proName]}

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Chemical Structure| 870221-17-3
Chemical Structure| 870221-17-3
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Product Details of [ 870221-17-3 ]

CAS No. :870221-17-3 MDL No. :MFCD12922706
Formula : C9H6ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 191.62 Pubchem ID :-
Synonyms :

Safety of [ 870221-17-3 ]

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Application In Synthesis of [ 870221-17-3 ]

* 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.

  • Downstream synthetic route of [ 870221-17-3 ]

[ 870221-17-3 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 870221-17-3 ]
  • [ 586-30-1 ]
  • [ 926277-91-0 ]
  • 2
  • [ 870221-17-3 ]
  • [ 2458-12-0 ]
  • [ 870221-16-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine triflouroacetate; In dimethyl sulfoxide; at 95℃; for 65.0h; Example 55 Synthesis of 4-Methyl-3-(3-pyrimidin-4-yl-pyridin-2- ylamino) -benzoic acid; 4- (2-Chloro-pyridin-3-yl)-pyrimidine (10.4 g, 54 mmol), 3- amino-4-methylbenzoic acid (19.4 g, 128 mmol), 17 g Et3N-TFA salt (The liquid Et3N-TFA reagent was generated by adding 2.5 mL TFA dropwise to a 0 C solution of 3 mL Et3N in isopropanol, then concentrating by rotary evaporator followed by 30 minutes under high vacuum. ), and 15 mL DMSO were mixed together in a sealed tube under argon. The mixture was stirred at 95 C for 65 h. 'After cooling to RT, the residue was sonicated in 100 mL methanol to break up the solids, then filtered to obtain product as a yellow solid. MS m/z = 307 [M+H]+. Calc'd for C17H14N402: 306.33.
  • 3
  • [ 166196-84-5 ]
  • [ 3473-63-0 ]
  • [ 870221-17-3 ]
  • 4
  • [ 870221-17-3 ]
  • 4-methyl-N-phenyl-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)benzamide [ No CAS ]
  • 5
  • [ 870221-17-3 ]
  • 4-methyl-3-((3-(4-pyrimidinyl)-2-pyridinyl)oxy)-N-(3-(trifluoromethyl)phenyl)benzamide [ No CAS ]
  • 6
  • [ 870221-17-3 ]
  • 4-methyl-3-(3-pyrimidin-4-yl-pyridin-2-yloxy)-<i>N</i>-(4-trifluoromethyl-phenyl)-benzamide [ No CAS ]
  • 7
  • [ 870221-17-3 ]
  • 4-methyl-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)-N-(3-(trifluoromethyl)phenyl)benzamide [ No CAS ]
  • 8
  • [ 870221-17-3 ]
  • 4-methyl-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)-N-(4-(trifluoromethyl)phenyl)benzamide [ No CAS ]
  • 9
  • [ 870221-17-3 ]
  • 4-methyl-N-(2-(methyloxy)-5-(trifluoromethyl)phenyl)-3-((3-(4-pyrimidinyl)-2-pyridinyl)oxy)benzamide [ No CAS ]
  • 10
  • [ 870221-17-3 ]
  • N-(3-(3-(dimethylamino)propyl)-5-(trifluoromethyl)phenyl)-4-methyl-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)benzamide [ No CAS ]
  • 11
  • [ 870221-17-3 ]
  • 4-methyl-N-(2-(4-morpholinyl)-5-(trifluoromethyl)phenyl)-3-((3-(4-pyrimidinyl)-2-pyridinyl)oxy)benzamide [ No CAS ]
  • 12
  • [ 870221-17-3 ]
  • 4-methyl-N-(2-(1-piperidinyl)-5-(trifluoromethyl)phenyl)-3-((3-(4-pyrimidinyl)-2-pyridinyl)oxy)benzamide [ No CAS ]
  • 13
  • [ 870221-17-3 ]
  • 4-methyl-N-(2-(1-piperidinyl)-5-(trifluoromethyl)phenyl)-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)benzamide [ No CAS ]
  • 14
  • [ 55676-21-6 ]
  • [ 870221-17-3 ]
  • 15
  • 1-(2-chloro-pyridin-3-yl)-3-dimethylamino-propenone [ No CAS ]
  • [ 3473-63-0 ]
  • [ 870221-17-3 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; at 40 - 48℃; Step 2. Preparation of 4-(2-Chloro-pyridin-3-yl)-pyrimidin; Sodium methoxide was generated over a period of 1.5 h by the intermittent addition of small chunks of sodium metal (8.3 g total, 360 mmol) to 400 mL dry methanol under N2 at room temperature, using a bath of 50Q mL IpOH at room temperature as a heat sink. Formamidine acetate (42.7 g, 410 mmol) was added, followed ten minutes later by the enaminone (30.6 g, 146 mmol). The reaction was stirred overnight under a N2- filled balloon at an internal temperature of 40 C. After 20 h, the mixture was stirred at 48 C for 4 h. Additional formamidine acetate (7.0 g) was added and the mixture was stirred overnight at 44 C. The mixture was concentrated by rotary evaporator, taken up in ethyl acetate and extracted with saturated aqueous NaHC03. The aqueous layer was back- extracted with EtOAc. The combined organic layers (1.2 L) were dried over Na2S04 and concentrated. The residue was purified by flash vacuum filtration chromatography (300 g silica) in 3: 1 to 2:1 hexane/EtOAc to provide a solid white title compound. MS m/z = 192 [M+H]+. Calc'd for C9H6ClN3: 191.62.
  • 16
  • [ 870221-17-3 ]
  • [ 2365-85-7 ]
  • 4-fluoro-3-(3-pyrimidin-4-yl-pyridin-2-ylamino)-benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine triflouroacetate; at 95℃; Step 1. Preparation of 4-Fluoro-3-(3-pyrimidin-4-yl- pyridin-2-ylamino) -benzoic acid; 4- (2-Chloro-pyridin-3-yl)-pyrimidine (240 mg, 1.2 mmol), 3- amino-4-fluorobenzoic acid (217 mg, 1.40 mmol), and 340 mg Et3N-TFA salt were mixed together in a sealed tube under argon. (The liquid Et3N-TFA reagent was generated by adding 2.5 mL TFA dropwise to a 0 C solution of 3 mL Et3N in isopropanol, then concentrating by rotary evaporator followed by 30 minutes under high vacuum. ). The mixture was melted at 95 C, and heating was continued overnight. The residue was triturated with a small amount of methanol and filtered to obtain the title compound as a solid. MS m/z = 311 [M+H]+. Calc'd for C16H11FN4O2: 310.29.
  • 17
  • [ 870221-17-3 ]
  • [ 2835-96-3 ]
  • 3-methyl-4-(3-pyrimidin-4-yl-pyridin-2-yloxy)-phenylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 20 - 210℃; for 0.333333h;Microwave irradiation; Example 57 Synthesis of 3-Methyl-4-(3-pyrimidin-4-yl-pyridin-2-yloxy)- phenylamine; To 4-amino-2-methyl-phenol (193 mg, 1.57 mmol) was added Cs2C03 (1.02 g, 3.14 mmol) and NMP (2.0 mL). The mixture was heated for 5 minutes at 100 °C, cooled to RT and 4-(2- chloro-pyridin-3-yl) -pyrimidine (300 mg, 1.57 mmol) was added. The mixture was heated in the microwave to 210 °C for 20 minutes, cooled, filtered through a plug of cotton and purified by reverse-phase HPLC (Gilson, acidic mobile phase) to yield 3-methyl-4-(3-pyrimidin-4-yl-pyridin-2-yloxy)- phenylamine. MS m/z = 279 [M+1]+. Calc'd for C16H14N40: 278.32.
  • 18
  • [ 870221-17-3 ]
  • [ 69-72-7 ]
  • 4-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In dimethyl sulfoxide; at 200℃; for 0.166667h;Microwave irradiation; Example 58 Synthesis of 4-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzoic acid; A mixture of 4- (2-chloro-pyridin-3-yl)-pyrimidine, hydroxy-benzoic acid and Cs2CO3 in DMSO was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 200 C for 10 minutes. The reaction mixture was cooled to RT and diluted with 60 mL of EtOAc. The product was precipitated from the solution. The mixture was then washed with 20 mL of water twice. The solid was collected by filtration and dried in an oven at 50 C to afford off white solid as desired product. MS m/z = 294 [M+1]+. Calc'd for C16H11N3O3: 293.28.
  • 19
  • [ 870221-17-3 ]
  • [ 154057-15-5 ]
  • ethyl 3-(3-(pyrimidin-4-yl)pyridin-2-ylamino)-4-(trifluoromethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium t-butanolate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃; Step 3. Preparation of ethyl 3-(3-(pyrimidin-4-yl)pyridin- 2-ylamino)-4- (trifluoromethyl)benzoate; 4- (2-Chloropyridin-3-yl)pyrimidine (1.5 g, 7.8 mmol), ethyl 3-amino-4- (trifluoromethyl)benzoate (2.0 g, 8.6 mmol), Sodium tert-butoxide (1.1 g, 12 mmol), rac-2,2'- Bis(diphenylphosphino)-l,l'-binaphthyl (0.49 g, 0.78 mmol) were all mixed together in toluene (25ml) and degassed under vacuum. Nitrogen was bubbled into the reaction for 5 minutes and then Palladium (II) acetate (0.088 g, 0.39 mmol) was added. The mixture was heated to 80 C and stirred overnight. The reaction was diluted with ethyl acetate and washed with an aqueous saturated solution of sodium bicarbonate, water and brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient 5 to 40 % ethyl acetate in hexanes to afford ethyl 3-(3-(pyrimidin-4- yl)pyridin-2-ylamino)-4- (trifluoromethyl)benzoate as a brown solid. MS m/z = 389 [M+1]+. Calc'd for C19H15F3N4O2: 388.11.
  • 20
  • [ 870221-17-3 ]
  • [ 660838-05-1 ]
  • [4-methyl-3-(3-pyrimidin-4-yl-pyridin-2-ylamino)-phenyl]-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 130℃; Step 2. Preparation of [4-methyl-3-(3-pyrimidin-4-yl- pyridin-2-ylamino) -phenyl]-carbamic acid tert-butyl ester; The title compound was prepared according to the procedure decribed in Tetrahedron 2001,51, 7027-7034. Pd(OAc)2 (47 mg, 0.21 mmol), and rac-BINAP (131 mg, 0.21 mmol) were stirred in toluene (12 mL) at RT for 12 minutes. This mixture was added to <strong>[870221-17-3]4-(2-chloro-pyridin-3-yl)-pyrimidine</strong> (1.01 g, 5.24 mmol), (3-amino-4-methyl-phenyl) -carbamic acid tert-butyl ester (1.63 g, 7.34 mmol), and K2C03 (14.5 g, 105 mmol) in toluene (40 mL). The mixture was heated overnight at 130 C in a sealed tube. The cooled reaction was filtered through a pad of Celite, partially concentrated and the resulting solid was filtered to yield [4-methyl-3-(3- pyrimidin-4-yl-pyridin-2-ylamino) -phenyl]-carbamic acid tert-butyl ester.
  • 21
  • [ 870221-17-3 ]
  • [ 870221-09-3 ]
  • N-(3-(1-methylethyl)phenyl)-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine triflouroacetate; In dimethyl sulfoxide; at 90℃; for 22.0h; Example 199 Synthesis of N-(3-(1-methylethyl)phenyl)-3-((3-(4- pyrimidinyl) -2-pyridinyl)amino)benzamide; To 3-amino-N- (3-isopropyl-phenyl)-4-methyl-benzamide mg, 1.2 mmol), 4- (2-chloropyridin-3-yl)pyrimidine mg, 0.52 mmol) and DMSO (0.15 mL) was added NEt3-TFA (0.11 mL). The resulting slurry was stirred for 22 hours at 90 C. The crude material was purified by silica gel chromatography (40-60% EtOAc/hexanes) to yield the title compound as a yellow solid. MS m/z = 410 [M+1]+. Calc'd for C25H23N50: 409.49.
  • 22
  • [ 870221-17-3 ]
  • [ 870221-13-9 ]
  • 3,4-dichloro-N-(4-methyl-3-((3-(4-pyrimidinyl)-2-pyridinyl)amino)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 130℃; Step 2. Preparation of 3,4-dichloro-N-(4-methyl-3-((3-(4- pyrimidinyl) -2-pyridinyl)amino)phenyl)benzamide; 4- (2-Chloro-pyridin-3-yl)-pyrimidine (60 mg, 0.30 mmol), N- (3-amino-4-methyl-phenyl) -3,4-dichloro-benzamide (107 mg, 0.36 mmol), Pd(OAc)2 (4 mg, 0.012 mmol), rac-BINAP (8 mg, 0.012 mmol) and KzC03 (829 mg, 6.0 mmol) in toluene (3.0 mL) were reacted overnight at 130 C. The reaction was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous NazS04, filter, concentrated and purified by reverse-phase HPLC (Gilson, acidic mobile phase) yielding the title compound. MS m/z = 450,452 [M]+ and [M+2]+. Calc'd for C23H17Cl2N5O: 450.33.
  • 23
  • [ 870221-17-3 ]
  • [ 364-76-1 ]
  • N-(4-fluoro-3-nitrophenyl)-3-(pyrimidin-4-yl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 130℃; Step 1. Preparation of N-(4-fluoro-3-nitrophenyl)-3- (pyrimidin-4-yl) pyridin-2-amine; 4- (2-Chloro-pyridin-3-yl)-pyrimidine (60 mg', 0.30 mmol), 4- fluoro-3-nitrobenzenamine (56 mg, 0.36 mmol), Pd(OAc)2 (4 mg, 0 . 012 mmol), rac-BINAP (8 mg, 0 . 012 mmol) and K2C03 (829 mg, 6.0 mmol) in toluene (3.0 mL) were reacted overnight at 130 C. The reaction was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2S04, filter, concentrated and purified by silica gel chromatography (0-100% EtOAc/hexanes) yielding the title compound. MS m/z = 312 [M+1]+. Calc'd for C15H10FN5O2: 311.28.
  • 24
  • [ 870221-17-3 ]
  • [ 943606-87-9 ]
  • 6-methyl-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With lithium hexamethyldisilazane;tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In tetrahydrofuran; at 70℃; Example 7Preparation of 6-methyl-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)-NI-(3- (trifluoromethyl)phenyl)isoquinoline-l,5-diamine <n="70"/>6-Methyl-N'-(3-(trifluoroinethyl)pheny])isoquinoline-l,5-dianiine (0.100 g, 0.30 mmol), 4-(2-chlororhoyridin-3-yl) pyrimidine (0.057 g, 0.30 mmol), dicycIohexylphosphino)-N,N- dimethylaminobiphenyl (0.0094 g, 0.024 mmol), and Pd2(dba)3 (0.010 g, 0.012 mmol) were all placed in a sealed tube containing 5 mL of anhydrous THF. Lithium bis (trimethylsilyl)amide (1.0 M in THF, 0.90 mL, 0.90 mmol) was then added to the mixture and nitrogen was bubbled into the reaction mixture for 5 min. The tube was capped and the reaction heated to 700C overnight. The reaction was allowed to cool to room temperature and quenched with methanol. The volatiles were removed in vacuo. The residue was taken up in ethyl acetate and washed (2x) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and the purified by column chromatography on silica gel using a gradient of 20 to 60 % EtOAc in hexanes to give 6-methyl-N5-(3-(pyrimidin-4- yl)pyridin-2-yI)-N1-(3-(trifluoromethyl)phenyl)isoquinoline-l,5-diamine as a yellow solid (80 mg, 56%). MS (M+H)+ 473.
  • 25
  • [ 870221-17-3 ]
  • [ 1093101-72-4 ]
  • N1-(4-chlorophenyl)-6-methyl-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)isoquinoline-1,5-diamine [ No CAS ]
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