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[ CAS No. 152460-10-1 ]

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CAS No. :152460-10-1 MDL No. :MFCD09028125
Formula : C16H15N5 Boiling Point : 537.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :277.32 g/mol Pubchem ID :9965429
Synonyms :

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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
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Application In Synthesis of [ 152460-10-1 ]

  • Upstream synthesis route of [ 152460-10-1 ]
  • Downstream synthetic route of [ 152460-10-1 ]

[ 152460-10-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 876-08-4 ]
  • [ 152460-10-1 ]
  • [ 404844-11-7 ]
YieldReaction ConditionsOperation in experiment
97.4% With triethylamine In tetrahydrofuran at 0℃; for 4 h; Example 15 Preparation of 4-((4-((5Z,8Z,llZ,14Z,17Z)-icosa-5,8,ll,14,17-pentaenoyl)piperazin-l- yl)methyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide (IV-5): [0311 ] The commercially available 6-methyl-N 1 -(4-(pyridin-3 -yl)pyrimidin-2- yl)benzene-l,3-diamine (10.0 g, 36.0 mmol) and Et3N (10.0 ml, 72.2 mmol) were taken up in THF (100 mL). The resulting solution was cooled to 0 °C with stirring and maintained for 10 min. A solution of 4-(chloromethyl)benzoyl chloride (7.8 g, 41.4 mmol) in THF (50 mL) was added dropwise. After stirring at 0 °C for four hours, water (500 ml) was added dropwise to the reaction mixture, and a light-yellow precipitate appeared. The resulting precipitate was collected by suction filtration, washed with water ( 2 x 500 ml), and dried under reduced pressure to afford 4-(chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2- yl)amino)phenyl)benzamide (15.1 g, yield: 97.4 percent) as a light-yellow solid. This material (4 g, 93 mmol) and tert - butyl piperazinecarboxylate (8.8 g, 465 mmol) were dissolved in N- methyl-2-pyrrolidone (20 mL). The solution was reacted under microwave conditions at 120 °C for 1 h. After cooling to room temperature, CH2CI2 (50 mL) was added to the reaction mixture. The resulting mixture was extracted with 1M HC1 (20 mL). The acidic aqueous phase was neutralized with sodium carbonate, and then extracted with CH2CI2 (2 x 50 mL). The combined organic layers were dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (pentane/EtOAc) to give 4 g of tert-butyl 4-(4-((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2- yl)amino)phenyl)carbamoyl)benzyl)piperazine-l-carboxylate (72percent yield) as a yellow solid. This material (580 mg, 1 mmol) was dissolved in a solution of HC1 in EtOAc (5 mL, 4 M). The resulting reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure to afford the HC1 salt of N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin- 2-yl)amino)phenyl)-4-(piperazin-l-ylmethyl)benzamide.MS (EI) calculated for C28H29N7O: 479.58; Found: 480 [M+H]+(5Z,8Z,l lZ,14Z,17Z)-Eicosa-5,8,l l,14,17-pentaenoic acid (EPA, 0.27 g, 0.92 mmol) was taken up in 15 mL of CH2C12 along with HATU (0.47 g, 1.24 mmol), Et3N (0.25 g, 2.49 mmol) and the HC1 salt of N-(4-methyl-3-((4-(pyridin-3- yl)pyrimidin-2-yl)amino)phenyl)-4-(piperazin-l-ylmethyl)benzamide (0.4 g, 0.83 mmol). The resulting reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then diluted with CH2CI2 (100 mL). The organic layer was washed with aq.NH4Cl (3 x 100 mL), brine (3 x 100 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (Gradient elution, 2: 1 pentane/EtOAc to 100percent EtOAc) to afford 0.4 g of 4-((4-((5Z,8Z,l lZ,14Z,17Z)-icosa- 5,8,11,14,17-pentaenoyl)piperazin- 1 -yl)methyl)-N-(4-methyl-3 -((4-(pyridin-3 -yl)pyrimidin- 2-yl)amino)phenyl)benzamide (62percent yield). MS (EI) calculated for C48H57N702: 764.01; Found: 765.05 [M+H] +
95% With potassium carbonate In tetrahydrofuran at 0 - 20℃; for 1.16667 - 4.25 h; Example 6 4-Methyl-N-3-(4-pyridin-3-ylpyrimidin-2-yl)-benzene- 1,3- diamine (18.488 g, 0.067 M) was dissolved in THF (255 mL), freshly EPO <DP n="27"/>ground potassium carbonate (19.870 g, 0.143 M) was added and then the mixture was cooled down to 0°C. A solution of 4- chloromethylbenzoyl chloride (13.863 g, 0.073 M) in THF (69 niL) was added dropwise within 15 minutes while temperature of the reaction mixture was maintained at 00C. The reaction mixture was stirred at this temperature for 2 hours and for another 2 hours at room temperature. Water was added dropwise at a very low rate. Temperature of the reaction has risen to 26°C. At this temperature dropwise addition of water was continued with cooling. Cooling was discontinued when temperature dropped below 19°C. When water addition was completed (in total 543 mL), temperature of the reaction mixture was 26°C. The reaction mixture was stirred for further 30 min. A solid precipitate was filtered off and washed with water (150 mL) to afford 28.06 g (yield 97percent) of the title compound in the form of a colourless crystalline solid.M.p. 211-212°C. 1H NMR (DMSO-dβ): 10.24 (IH, s), 9.28 (IH, d, J=l,8), 8.99 (IH, s), 8.69 (IH, dd, J=4.8-1.4), 8.52 (IH, d, J=5,2), 8.48 (IH, dt, J=8.2-1.8), 8.09 (IH, d, J=2.0), 7.96 (2H, d, J=8.0), 7.51 (5H, m), 7.22 (IH, d, J=8.4), 4.85 (2H, s), 2.23 (3H, s). Example 7 4-Methyl-N-3-[(4-pyridin-3-yl)pyrimidin-2-yl]-benzene- 1,3- diamine (18.488 g, 0.067 M) was dissolved in THF (255 mL), freshly ground potassium carbonate (19.870 g, 0.143 M) was added and then the mixture was cooled down to 0°C. A solution of 4- chloromethylbenzoyl chloride (13.863 g, 0.073 M) in THF (69 mL) was added dropwise within 10 minutes while temperature of the reaction mixture was maintained at approximately 200C. The reaction mixture was stirred at room temperature for 1 hour. Water was added dropwise (in total 543 mL) while maintaining temperature EPO <DP n="28"/>of the reaction mixture at approximately 200C, and then the reaction mixture was stirred for 80 min. A solid precipitate was filtered off and washed with water (150 mL) to afford 28.37 g (yield 98percent) of the title compound. Example 8 4-Methyl-N-3-[(4-pyridin-3-yl)pyrimidin-2-yl]-benzene- 1 ,3- diamine (9.244 g, 33.3 niM) was dissolved in THF (128 mL), then a solution of potassium carbonate (9.935 g, 71.9 mM) in water (13 mL) was poured in. The mixture was cooled down to 0°C and a solution of 4-chloromethylbenzoyl chloride (6.932 g, 36.7 mM) in THF (30 mL) was added dropwise within 15 minutes. The reaction mixture was stirred at 00C for 2 hours. Water (260 mL) was added dropwise with stirring and cooling the reaction flask and then at room temperature for further 30 min. A solid precipitate was filtered off and washed with water (120 mL) to afford 13.62 g (yield 95percent) of the title compound.
94% With triethylamine In tetrahydrofuran at 0 - 20℃; for 7 h;       4-(Chloromethyl)benzoylchloride (0.41 g, 2.16 mmol) wasslowly added to the mixture of compound 3(0.50g, 1.8 mmol) andEt3N(0.36 g, 3.6 mmol) in20 mL THF  at  0 oC for 1 h. The resulting mixturewas stirred atroom temperature for 6 h. After the addition ofH2O,solid was formed and washed with water 5times to give theproduct with  94percent yield (0.73 g, 1.69 mmol). 1H NMR (300 MHz, DMSO)δ 10.24 (s, 1H), 9.28(d, J = 1.5 Hz,1H), 8.98 (s, 1H), 8.68 (dd, J =  3.3 Hz, 1H), 8.52-8.46 (m, 2H), 8.10(d, J = 2.1 Hz, 1H), 7.96( d, J =  8.1 Hz, 2H), 7.60-7.40 (m, 5H), 7.21(d, J = 8.1 Hz, 1H), 4.84 (s, 2H), 2.23(s, 3H). 13CNMR (75 MHz, DMSO): δ164.9, 161.6, 161.1, 159.4, 151.4, 148.2, 140.1, 137.8, 137.1, 134.9, 134.4,132.2, 130.0, 128.7, 128.0, 127.7, 123.8, 117.2, 116.7, 107.5, 45.4, 17.7. HRMS(ESI) calcd. for C24H21ClN5O [M+H]+430.1435, found430.1433.
94.2%
Stage #1: With triethylamine In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: at 0℃; for 4 h;
_6-Methyl-N-(4-(pyridine-3-yl) pyrimidin-2-yl) benzene-1,3-diamine (1.24 g, 4.46 mmol) and TEA (1.4 mL, 8.92 mmol) was dissolved in THF (15 mL).
The resulting solution was cooled to 0° C. with stirring and maintained for 10 minutes.
A solution of 4-(chloromethyl)benzoyl chloride (0.97 g, 5.14 mmol) in THF (5 mL) was added dropwise.
After stirring at 0° C. for 4 hours, water (140 mL) was added dropwise to the reaction mixture, and a light-yellow precipitate appeared.
The resulting precipitate was collected by suction filtration, washed with water (300 mL), and dried under vacuum.
The crude product was purified by column chromatography (biotage: DMC/Methanol, 1-8percent, 25 CV).
The desired product was obtained (1.82 g, yield: 94.2percent) as a light-yellow solid; 1H NMR (500 MHz, CDCl3) δ 2.38 (s, 3H), 4.66 (s, 2H), 7.05 (s, 1H), 7.22 (m, 2H), 7.30 (m, 1H), 7.42 (d, 1H), 7.51 (d, 2H), 7.89 (m, 3H), 8.51 (m, 2H), 8.63 (s, 1H), 8.71 (d, 1H), 9.28 (s, IH). LC-MS (m/z) calculated, 429.14, found, 430.2 [M+H]+.
93% at 0℃; for 1 h; 5mmol6-Methyl-N1-(4-(3-substituted-pyridine)2-substituted pyrimidine-)benzene-1,3-diamine compound iAnd 7 mmol of triethylamine (Et3N) was cooled to zero degrees Celsius in 15 mL of N,N-dimethylformamide (DMF).Under stirring,5.5 mmol of 4-(chloromethyl)benzoyl chloride was added in portions and the reaction was stirred at zero degrees Celsius for 1 hour.The reaction system was extracted with ethyl acetate, the organic phases were combined and dried over anhydrous sodium sulfate.The solvent was removed on a rotary evaporator and the residue was isolated on a silica gel column.4-(Chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide compound j (yield: 93) percent).
86% at 0℃; Alkaline conditions 6-methyl-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (10) (5 mmol, 1.38 g) and DIEA (7.5 mmol, 968 mg) in 15 mL DMF at 0 °C was added 4-(chloromethyl)benzoyl chloride (5.5 mmol, 1.03 g) dropwisely, and the solution was stirred at 0 °C for 1 h. The system was quenched with water and extracted with EtOAc and dried with anhydrous Na2SO4. The solvents were removed under vacuum and the residue was purified by silica gel flash chromatography (EtOAc) to provide compound 11a (1.84 g, 86percent). 1H NMR (400MHz, DMSO-d6) δ 10.29 (s, 1H), 9.29 (s, 1H), 8.98 (s, 1H), 8.69 (s, 1H), 8.52 (s, 2H), 8.12 (s, 1H), 7.99 (s, 2H), 7.70–7.33 (m, 5H), 7.22 (s, 1H), 4.85 (s, 2H), 2.24 (s, 3H). 13C NMR (101MHz, DMSO-d6): δ 164.95, 161.53, 161.08, 159.36, 151.21, 148.05, 140.83, 137.73, 137.05, 134.78, 134.43, 132.15, 130.00, 128.64,128.02, 127.64, 123.73, 117.23, 116.87, 107.51, 45.41, 17.60. HRMS (ESI, m/z) [M+H]+ calcd for C24H21ClN5O: 430.1435, found: 430.1436 [21].
68% With triethylamine In dichloromethane at 0 - 20℃; for 18 h; a) Synthesis of compound 2a Compound 1a (5.0 g, 18.0 mmol; Manufacturer: Shanghai Xugang bio-tech limited company), and triethylamine (3.6 g, 35.6 mmol) were dissolved in dichloromethane (400 ml), 4-(chloromethyl)benzoyl chloride (4.0 g, 21.3 mmol) was dissolved in dichloromethane (100 ml), at 0 °C, add the drops into the reaction solution, and end up to the room temperature, stir at room temperature for 18 hours, the solid precipitated, filtered and collected. Wash the solid with dichlomethane, then with water, to give the yellow solid compound 2a (5.3 g, 68percent yield). 1H NMR (400 MHz, DMSO-d6): δ 10.23 (s, 1 H), 9.28 (s, 1 H), 8.97 (s, 1 H), 8.69 (d, J = 4.4 Hz, 1 H), 8.52 (m, 2 H), 8.09 (s, 1 H), 7.97 (d, J = 7.6 Hz, 2 H), 7.59-7.42 (m, 5 H), 7.22 (d, J = 8.0 Hz, 1 H), 4.84 (s, 2 H), 2.23 (s, 3 H). MS (ESI+) m/z: 430 [M +1]+.
67% With triethylamine In chloroform at 0 - 5℃; for 4 - 5 h; Procedure : 80 L chloroform is charged into the reactor 12.8 Kgs of N-(5-amino~2-methylphenyl)-4-(3-pyridyl)~2-pyrimidine of the formula (VII) amine is charged into thereactor. Stirred for 15 minutes to get clear solution 9.3 Kg of triethylamine is charged.To the reaction mass 10.4 Kg of 4-(Chloromethyl)benzoyl chloride dissolved in 70 Lchloroform is charged slowly during 4-5 hours at 0-5C. The compound of the formula(II)is centrifuged and washed with 15 L DM water and 15 L Ethyl acetate, the product isdried at 60-70C.Yield: 13.9 Kg (70percent)MR: 181-183C.Purity by TLC : Single spotStep-4 : Preparation of 4-(chloromethyl)-N-4-methyl-3-[(4-(3-pyridinyl)-2-pyritnidinyl]imino]phenyl benzamide (II)8 L chloroform is charged into the reactor 1.28 Kgs of N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine of the formula (VII) amine is charged into the ;tor. Stirred for 15 minutes to get clear solution 0.9 Kg of triethylamine is charged.the reaction mass 1.04 Kg of 4-(Chloromethyl)benzoyl chloride dissolved in 7 L)roform is charged slowly during 2 hours at 0-5C, The compound of the formulais centrifuged and washed with 2 L DM water and 2 L Ethyl acetate, the product isid at 60-70C.Id: 1.3 5 Kg (68percent).: 180-182C.ity by TLC : Single spot Step-4 : Preparation of 4-(chloromethyl)-N_-4-methyl-3-[(4-(3-pyridinyl)-2-pyrimidinyl]aminojphenyl benzamide (II) L chloroform is charged into the reactor 1.28 Kgs of N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine of the formula (VII) amine is charged into thereactor. Stirred for 15 minutes to get clear solution 0.9 Kg of triethylamine is charged.To the reaction mass 1.04 Kg of 4-(Chloromethyl)benzoyl chloride dissolved in 7 Lchloroform is charged slowly during 3 hours at 5-10C. The compound of the formula(II)is centrifuged and washed with 2 L DM water and 2 L Ethyl acetate, the product isdried at 60-70C.Yield: 1.34 Kg (67percent)MR: 180-182C.Purity by TLC : Single spotStep-4 : Preparation of 4-(chloromethyl)-TSf_-4-methyl-3-[(4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl benzamide (II)8 L chloroform is charged into the reactor 1.28 Kgs of N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine of the formula (VII) amine is charged into the reactor. Stirred for 15 minutes to get clear solution 0.9 Kg of triethylamine is charged. To the reaction mass 1.04 Kg of 4-(Chloromethyl)benzoyl chloride dissolved in 7 Lchloroform is charged slowly during 2 hours at 5-10C. The compound of the formula(II)is centrifuged and washed with 2 L DM water and 2 L Ethyl acetate, the product isdried at 60-70C.Yield: 1.36 Kg (68percent)MR: 181-183C.Purity by TLC : Single spot

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Reference: [1] Patent: WO2011/95835, 2011, A1, . Location in patent: Page/Page column 32
[2] Patent: CN107805240, 2018, A, . Location in patent: Paragraph 0075-0078
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