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CAS No. :1802924-14-6 MDL No. :N/A
Formula : C17H28N4O5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 368.43 Pubchem ID :-
Synonyms :

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Signal Word: Class:N/A
Precautionary Statements: UN#:N/A
Hazard Statements: Packing Group:N/A

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* 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 [ 1802924-14-6 ]

[ 1802924-14-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1802924-13-5 ]
  • [ 142-25-6 ]
  • [ 1802924-14-6 ]
YieldReaction ConditionsOperation in experiment
99% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 60℃; for 2h; 1.2 Step 2. Preparation of compound 4_3. N,N,N'-trimethylethylenediamine (3.59 mL, 27.2 mmol) and DIPEA (5.24 mL, 31.3 mmol) were added to a solution of aniline 4_2 (6.10 g, 20.9 mmol) in DMF (10 mL) at room temperature. Reaction mixture was stirred at 60 °C for 2 hours. Resulting mixture was poured into water, product was extracted with ethyl acetate. The combined organic layers were washed with water and saturated NaCl solution, dried with Na2SO4, filtered and concentrated under vacuum. Yield of the compound 4_3 was 7.62 g (99%).
98% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 45℃; for 2h; Inert atmosphere; 2 preparation of 4-(N,N,N'-trimethylethylenediamine)-2-methoxy-5-nitroanilino tert-butyl formate Under nitrogen / argon,200 mg (0.698 mmol)4-fluoro-2-methoxy-5-nitroanilanate,78.47 mg (0.768 mmol) of N, N, N'-trimethylethylenediamine,117.27 mg (0.907 mmol) of N, N-diisopropylethylamine and10mlN, N-MethylacetamideplusCome in50mlIn a single-necked flask,Heating to 45 ° C, stirring reaction 2h,To the room temperature, add 40ml of water and extract twice with 20ml methylene chloride. The organic layers were combined, washed with saturated brine, dried, filtered and dried to give 252 mg of bright orange solid in 98% yield.
93.2% With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 4h; General procedures for preparation of the target intermediates (5a-h) General procedure: Intermediate 4a (1.00mmol), amines (1.5mmol), K2CO3 (2.00mmol) were mixed in dried DMF (6mL) at room temperature, then heated to 85°C in oil bath and stirred for 4h. The reactions were monitored by TLC until the process finished completely, then cool to room temperature. Sequentially, ethyl acetate (20mL) was added, then washed with brine (10mL×3). The organic phase was separated, dried over anhydrous Na2SO4, filtered, then the filtrate was evaporated under reduced pressure. The crude products were purified by silica gel chromatography and dried in a vacuum oven to give pure intermediates (5a-h). tert-butyl(4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)carbamate (5a) Yield: 93.2%; white solid; 1H NMR (600MHz, DMSO-d6) δ 8.16 (s, 1H), 8.10 (s, 1H), 6.73 (s, 1H), 3.89 (s, 3H), 3.21 (t, J=6.8Hz, 2H), 2.80 (s, 3H), 2.43 (t, J=6.8Hz, 2H), 2.13 (s, 6H), 1.45 (s, 9H). MS (ESI) m/z (%): 269.2 [M+H] +
93.2% With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 4h; General procedures for preparation of the target intermediates (5a-h) General procedure: Intermediate 4a (1.00mmol), amines (1.5mmol), K2CO3 (2.00mmol) were mixed in dried DMF (6mL) at room temperature, then heated to 85°C in oil bath and stirred for 4h. The reactions were monitored by TLC until the process finished completely, then cool to room temperature. Sequentially, ethyl acetate (20mL) was added, then washed with brine (10mL×3). The organic phase was separated, dried over anhydrous Na2SO4, filtered, then the filtrate was evaporated under reduced pressure. The crude products were purified by silica gel chromatography and dried in a vacuum oven to give pure intermediates (5a-h). tert-butyl(4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)carbamate (5a) Yield: 93.2%; white solid; 1H NMR (600MHz, DMSO-d6) δ 8.16 (s, 1H), 8.10 (s, 1H), 6.73 (s, 1H), 3.89 (s, 3H), 3.21 (t, J=6.8Hz, 2H), 2.80 (s, 3H), 2.43 (t, J=6.8Hz, 2H), 2.13 (s, 6H), 1.45 (s, 9H). MS (ESI) m/z (%): 269.2 [M+H] +
92% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 60℃; for 2h; N1,N1,N2-Trimethylethane-1,2-diamine (15.8 g, 155 mmol) was added to a solution of N-(t-butoxycarbonyl)-4-fluoro-2-methoxy-5-nitroanilide (37 g, 129 mmol) and DIPEA (16.6 g, 129 mmol) in DMA (400 mL). The mixture was heated to 60 °C and stirred at this temperature for 2h. After cooling to rt, the reaction was diluted with water (1 L) and extracted with DCM (300 mL x3). The combined extracts were dried over anhydrous magnesium sulfate. The solvent was removed under vacuum to give N-(t-butoxycarbonyl) )-4-(N,1-(2-(N,N-dimethylamino)ethyl)-N,1-methyl)amino)-2-methoxy-5-nitroanilide as an orange solid (44 g, 92%). 1HNMR (300 MHz, DMSO-d6): G 8.14- 8.10 (m, 1 H), 6.72 (s, 1 H), 3.88 (s, 3 H), 3.21- 3.18 (m, 2 H), 2.79 (s, 3 H), 2.45-2.43 (m, 2 H), 2.13 (s, 6 H), 1.44 (s, 9 H).
85% With N-ethyl-N,N-diisopropylamine at 90℃; for 6h; Inert atmosphere; 2-a.d Step d: The compound 2-a-4 (11.46g, 40mmol) was dissolved DMA (60mL) at was added N, N, N'- trimethyl-ethylenediamine (4.90g, 48mmol), N, N- di diisopropylethylamine (7.74g, 60mmol). The mixture under nitrogen, and heated to 90 deg. C for 6 hours. After cooling to room temperature, poured into ice water, and extracted with ethyl acetate (400mL). The organic phase was separated, washed with brine (300mL). Dried over anhydrous sodium sulfate, and filtered. The filtrate was spin-dried to give an orange solid 2-a-5 (12.51g, yield: 85%). MS m/z (ESI): 369 [M+H]+, purity = 98% (UV214).
85% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 90℃; for 6h; Step 2: Step 2: Compound 2a2 (11.46 g, 40 mmol) was dissolved in 60 ml N,N-dimethylacetamide, and N,N,N′-trimethyl-ethylenediamine (4.90 g, 48 mmol), N,N-diisopropylethylamine (7.74 g, 60 mmol) were added and heated to 90° C. and stirred for 6 h. The reaction progress was monitored by TLC. After completion of the reaction, the reaction solution was cooled to room temperature, poured into ice water, extracted with ethyl acetate, washed with water and saturated brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the title product compound 2a3 (12.51 g, 85%). It was used directly in the next reaction. MS m/z (ESI): 369 [M+H]+.
85% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 90℃; for 6h; 2 Step 2: The substrate of tert-butyl 4-fluoro-2-methoxy-5-nitrophenyl carbamate a2 (11.46 g, 40 mmol) was dissolved in 60 ml N,N-dimethylacetamide, and N,N,N′-trimethyl-ethylenediamine (4.90 g, 48 mmol) and N,N-diisopropylethylamine (7.74 g, 60 mmol) were added. The mixture was heated to 90° C. and stirred for 6 h. The reaction progress was monitored by TLC. After the substrate was completely consumed, the reaction mixture was cooled to room temperature, poured into ice water, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title product a3 (12.51 g, 85%) which was used directly in the next reaction. MS m/z(ESI): 369 [M+H]+.
85% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 90℃; for 6h; 2 The reaction substrate tert-butyl 4-fluoro-2-methoxy-5-nitrophenylcarbamate a2 (11.46 g, 40 mmol) was dissolvedin 60 ml of N,N-dimethylacetamide, and N,N,N’-trimethylethylenediamine (4.90 g, 48 mmol) and N,N-diisopropylethylamine(7.74 g, 60 mmol) were added. The mixture was heated to 90 °C and stirred for 6 hours. The progress ofthe reaction was checked by TLC. After the reaction of the substrate was complete, the reaction mixture was cooled toroom temperature, poured into iced water, extracted with ethyl acetate, washed with saturated brine, dried over anhydroussodium sulfate and concentrated under reduced pressure to give the target product a3 (12.51 g, 85%) which was directlyused in the next step. MS m/z (ESI): 369 [M+H]+.
7.9 g With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 60℃; for 2h; {4-[(2-Dimethylamino-ethyl) -methyl-amino]-2-methoxy-5-nitrophenyl}-carbamic acid t-butyl ester N1,N1,N2-Trimethylethane-1,2-diamine (2.7 g, 27.0 mmol) was added to a solution of (4-fluoro-2-methoxy-5-nitro-phenyl)-carbamic acid t-butyl ester (6.3g, 22.0 mmol)and DIPEA (N,N-Diisopropylethylamine) (3.82 mL, 22.0 mmol) in DMA (N,N-Dimethylacetamide) (100 mL). The mixture was heated to 60 °C and stirred at this temperature for 2h. Water (200 mL) was added to the reaction mixture, which was then extracted with DCM(50 mL*3). The combined extracts were dried over anhydrous magnesium sulfate. The solvent was removed under vacuum to give 7 as an orange solid (7.9 g, 97%); m.p. 92-94 °C (DCM). 1H NMR(DMSO) δ 8.12 (m, 2H), 6.74 (s, 1H), 3.90 (s, 3H), 3.21 (m, 2H), 2.81(s, 3H), 2.44 (m, 2H), 2.14 (s, 6H), 1.45 (s, 9H); 13C NMR (DMSO) δ153.5, 144.9, 132.1, 120.0, 102.4, 79.8, 56.8, 56.7, 53.1, 45.9, 40.8, 40.6, 40.4, 28.5, 27.9; IR 3441, 2979, 2359, 1708, 1546, 1162; MS calcd for C17H28N4O5 [M+H]+ 369.2132; found: 369.2136. The crude product was used in the next step without further purification.
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 110℃; B2.4 4) Synthesis of compound b2-5: 13.5 g of compound b2-4 was added to 200 ml of DMAC (N, N-dimethylethylAmide) with stirring, and then 2 eq of N, N, N'-trimethylethylenediamine and 3 eq of DIEA (N, N-diisopropylethylAmine) and the mixture was heated to 110 ° C overnight. The next day, the reaction was completed to obtain 22 g of the crude crude compound b2-5.
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Heating; 1 General procedure for preparation of compounds (10a-c) General procedure: Appropriate alkyl amine (2.7 g, 27.0 mmol) was added to a solutionof intermediate (9) (6.3 g, 22.0 mmol) and DIPEA (N,N-Diisopropylethylamine)(3.82 mL, 22.0 mmol) in DMF (100 mL). Themixture was heated to 60 C and stirred at this temperature for2 h. Water (200 mL) was added to the reaction mixture, whichwas then extracted with DCM (50 mL * 3). The combined extracts were dried over anhydrous magnesium sulfate. The solvent was removed under vacuum to afford compounds 10a-c, respectively,which were used without further purification.5.4.1. tert-Butyl (4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl) carbamate (10a)1H NMR (400 MHz, DMSO d6) d 8.12 (m, 2H), 6.74 (s, 1H), 3.90(s, 3H), 3.21 (m, 2H), 2.81 (s, 3H), 2.44 (m, 2H), 2.14 (s, 6H), 1.45(s, 9H); 13C NMR (100 MHz, DMSO d6) d 153.5, 144.9, 132.1,120.0, 102.4, 79.8, 56.8, 56.7, 53.1, 45.9, 40.8, 40.6, 40.4, 28.5,27.9; IR (KBr) cm1: 3441, 2979, 2359, 1708, 1546, 1162; ESI-MSm/z: 369.2 [M+H]+.
3.77 g With potassium carbonate at 60℃; 1.2 Intermediate 2 (3 g, 1 eq), N,N,N-trimethylethylenediamine (1.6 g, 1.5 eq),Potassium carbonate (4.99 g, 2 eq) was added to a 100 ml eggplant bottle in turn.The temperature was raised to 60 ° C, and the reaction was confirmed by TLC.After the reaction is completed, water is added to the mother liquor, and the insoluble matter is precipitated and filtered.The filter cake was washed with water to give 3.77 g of intermediate 3 red solid.The recovery rate is 97%.
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 110℃; Synthesis of B1-5: 13.5 g of raw B1-4 taken, added to 200ml of the DMA, the whole solution with stirring. 2eq added to N,N,N'-trimethyl-ethylenediamine and 3eq of DIEA, was heated to 110 °C and stirred overnight. The next day, the reaction is completed. To give 22g of a crude oil, the next step directly administered.
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 5h; 2 Step 2 Synthesis of Compound 37 tert-butyl (4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)carbamate N1,N1,N2-trimethylethane-1,2-diamine (2.14 g, 20.40 mmol) was added into the mixed solution of 33 tert-butyl (4-fluoro-2-methoxy-5-nitrophenyl)carbamate (4.0 g, 21.50 mmol) and 39 N,N-diisopropylethylamine (DIPEA, 4.92 mL, 27.20 mmol) in 40 N,N-dimethylformamide (28 mL), the reaction solution was reacted at 90° C. for 5 hours. After cooling to room temperature, it was diluted with water (100 mL), extracted with ethyl acetate (100 mL×3), and the organic phase was combined, washed with brine (100 mL×3), dried over anhydrous sodium sulfate, and the solvent was removed to afford 5.0 g of a brown oil, which was used in the next reaction without purification. LC-MS(APCI): m/z=369.3 (M+1).
2.24 g With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h; 3 Step 3:(4-(2-(Dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)carbamic acid tert-butyl ester tert-butyl (4-fluoro-2-methoxy-5-nitrophenyl)carbamate and added to DMFThen, potassium carbonate, N,N,N'-trimethylethylenediamine was added, and the reaction was continued at 60 ° C for 3 hours.After the reaction is completed, water is added to the reaction mixture, and the mixture is extracted with dichloromethane, and the organic layer is washed with water and washed with saturated sodium chloride solution.The organic layer was dried over anhydrous sodium sulfate.Evaporation to dryness gave 2.24 g of a red oil.
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 110℃; Synthesis of B1-5:Raw material B1-4 takes 13.5g,Add to 200ml of DMA,Dissolve under stirring.Then add 2eq of N, N, N’-trimethylethylenediamine and 3eq of DIEA,Warm to 110 ° C and stir overnight.The next day, the reaction was completed.After processing, 22g crude oily product was obtained, which was directly poured into the next step.
1.8 g With N-ethyl-N,N-diisopropylamine at 110℃; 1a.b Preparation of tert-butyl (4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)carbamate Dissolve tert-butyl (4-fluoro-2-methoxy-5-nitrophenyl) carbamate (1.5g, 5.24mmol) in DMA (15mL), add N,N,N'-trimethyl Ethylenediamine (0.8g, 7.86mmol) and N,N-diisopropylethylamine (1.01g, 7.86mmol) were heated to 110°C and reacted overnight. Add saturated sodium carbonate aqueous solution to adjust the pH to 8-9, extract with ethyl acetate, wash the organic phase with water, dry, and concentrate to obtain 1.8 g of light red oily liquid.
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 60℃; for 2h; 2.2 Step 2: A mixture of N 1, N 1, N 2-trimethylethane-1,2-diamine (24.5 g, 240.6 mmol), 71-1 (57.4 g, 200.5 mmol) and DIEA (25.9 g, 200.5 mmol) in dimethylacetamide (800 mL) was stirred at 60°C for 2 h. The mixture was quenched with water and extracted with dichloromethane. The combined organic layers were washed with water, dried over anhydrous Na 2SO 4, filtered and concentrated to afford 71-2 which was used directly in the next step without purification.
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 60℃; for 2h; 2.2 Step 2: A mixture of N 1, N 1, N 2-trimethylethane-1,2-diamine (24.5 g, 240.6 mmol), 71-1 (57.4 g, 200.5 mmol) and DIEA (25.9 g, 200.5 mmol) in dimethylacetamide (800 mL) was stirred at 60°C for 2 h. The mixture was quenched with water and extracted with dichloromethane. The combined organic layers were washed with water, dried over anhydrous Na 2SO 4, filtered and concentrated to afford 71-2 which was used directly in the next step without purification.
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 60℃; for 2h; 2.2 Step 2: A mixture of N 1, N 1, N 2-trimethylethane-1,2-diamine (24.5 g, 240.6 mmol), 71-1 (57.4 g, 200.5 mmol) and DIEA (25.9 g, 200.5 mmol) in dimethylacetamide (800 mL) was stirred at 60°C for 2 h. The mixture was quenched with water and extracted with dichloromethane. The combined organic layers were washed with water, dried over anhydrous Na 2SO 4, filtered and concentrated to afford 71-2 which was used directly in the next step without purification.
With potassium carbonate In acetonitrile at 80℃; for 12h; Step-5 In Reaction Scheme 2 above, the structure B1-P4 (2.2g, 7.685mmol) was dissolved in acetonitrile (50mL), and then at a room temperature, K2CO3 (2.124g, 15.371mmol) and N,N,N'-trimethylenediamine were added, and then it was stirred at 80 °C for 12 hours. When the reaction was completed, the reacted products were filtered and distilled under reduced pressure to obtain crude B1-P3. Without a separate separation process, it was used for the next reaction
With potassium carbonate In acetonitrile at 80℃; for 12h; Step-5 In Reaction Scheme 2 above, the structure B1-P4 (2.2g, 7.685mmol) was dissolved in acetonitrile (50mL), and then at a room temperature, K2CO3 (2.124g, 15.371mmol) and N,N,N'-trimethylenediamine were added, and then it was stirred at 80 °C for 12 hours. When the reaction was completed, the reacted products were filtered and distilled under reduced pressure to obtain crude B1-P3. Without a separate separation process, it was used for the next reaction
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 6h; 52 Take 13.1g (46mmol) of the intermediate in a 500mL single-neck flask, add 200mL of DMF, add 12.7g (92mmol) of potassium carbonate, and add 5.2g (51mmol) of N,N,N'-trimethylethylenediamine to it, Stir at 90°C for 6 hours, TLC detects that the raw materials have basically reacted completely, the solution is added dropwise to 800 mL of water, a precipitate is formed, filtered, and the filter cake is dried, which is directly used in the next reaction;

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