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[ CAS No. 147254-64-6 ] {[proInfo.proName]}

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Chemical Structure| 147254-64-6
Chemical Structure| 147254-64-6
Structure of 147254-64-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 147254-64-6 ]

CAS No. :147254-64-6 MDL No. :MFCD00920915
Formula : C17H11BrFN3O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 420.19 Pubchem ID :-
Synonyms :
AS-3201

Safety of [ 147254-64-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P304+P340+P312-P305+P351+P338-P337+P313 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 147254-64-6 ]

* 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 [ 147254-64-6 ]

[ 147254-64-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 112734-22-2 ]
  • [ 159213-26-0 ]
  • [ 147254-64-6 ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine; In N,N-dimethyl-formamide; at 20℃; (2) To a solution of <strong>[112734-22-2]4-bromo-2-fluorobenzylamine</strong> (0.93 g) and triethylamine (1.3 ml) in N,N-dimethylformamide (5 ml) was added a solution of ethyl (R)-2,5-dioxo-3-(2-trichloroacetylpyrrol-1-yl)pyrrolidine-3-carboxylate (1.16 g) in N,N-dimethylformamide (3 ml) dropwise at room temperature. This mixture was stirred at room temperature for 8 hours. This reaction mixture was diluted with ethyl acetate, then washed with 1M hydrochloric acid (three times), water (four times), and saturated brine successively, dried over magnesium sulfate, filtered and concentrated to give a crude product as yellow oil. This was purified by flash column chromatography (n-hexane:ethyl acetate=2:1) to give (3R)-2'-(4-bromo-2-fluorobenzyl)spiro[pyrrolidine-3,4'(1'H)-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2H')-tetraone (831 mg, 65percent). This product was further crystallized from n-hexane-ethyl acetate to give the desired product (385 mg) as crystal.Mp: 189-191° C. 1H NMR (400 MHz, DMSO-d6, 22° C.) delta: 12.2 (br s, 1H), 7.73 (dd, 1H, J=2.0, 3.2 Hz), 7.55 (dd, 1H, J=2.0, 9.6 Hz), 7.36 (dd, 1H, J=2.0, 8.4 Hz), 7.17-7.12 (m, 2H), 6.53 (dd, 1H, J=2.8, 4.0 Hz), 5.04 (d, 1H, J=15.2 Hz), 4.96 (d, 1H, J=15.6 Hz), 3.57 (s, 2H).
65% With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 8h; (2) To a solution of <strong>[112734-22-2]4-bromo-2-fluorobenzylamine</strong> (0.93 g) and triethylamine (1.3 ml) in N,N-dimethylformamide (5 ml) was added a solution of ethyl(R)-2,5-dioxo-3-(2-trichloroacetylpyrrol-1-yl)pyrrolidine-3-carboxylate (1.16 g) in N,N-dimethylformamide (3 ml) dropwise at room temperature. This mixture was stirred at room temperature for 8 hours. This reaction mixture was diluted with ethyl acetate, then washed with 1 M hydrochloric acid (three times), water (four times), and saturated brine successively, dried over magnesium sulfate, filtered and concentrated to give a crude product as yellow oil. This was purified by flash column chromatography (n-hexane: ethyl acetate =2:1) to give(3R)-2'-(4-bromo-2-fluorobenzyl)spiro[pyrrolidine-3,4'(1'H)-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2H')-tetraone (831 mg, 65percent). This product was further crystallized from n-hexane-ethyl acetate to give the desired product (385 mg) as crystal.Mp: 189-191° C. 1H NMR (400 MHz, DMSO-d6, 22° C.) delta: 12.2 (br s, 1H), 7.73 (dd, 1H, J=2.0, 3.2 Hz), 7.55 (dd, 1H, J=2.0, 9.6 Hz), 7.36 (dd, 1H, J=2.0, 8.4 Hz), 7.17-7.12 (m, 2H), 6.53 (dd, 1H, J =2.8, 4.0 Hz), 5.04 (d, 1H, J=15.2 Hz), 4.96 (d, 1H, J=15.6 Hz), 3.57 (s, 2H).
  • 2
  • [ 1000784-39-3 ]
  • [ 112734-22-2 ]
  • [ 147254-64-6 ]
YieldReaction ConditionsOperation in experiment
58% Example 12 Preparation of (3R)-2'-(4-bromo-2-fluorobenzyl)spiro[pyrrolidin-3,4'(1'H)-pyrrolo[1,2-a]pyrazin]-1',2,3',5(2'H)-tetraone 2,5-Dimethoxytetrahydrofuran (7.4 g) and 2.5percent aqueous acetic acid (50 g) were added to ethyl (2R)-2-amino-2-ethoxycarbonylsuccinimide (10 g)and the mixture was stirred at 70°C for 1.5 hours. The reaction solution was cooled and insoluble materials were dissolved by addition of ethyl acetate (50 ml) and stirring. The mixture was placed for a while and the organic layer was separated from the aqueous layer, washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo, diisopropylether (37 g) and ethyl acetate (9.2 g) were added to the residue and diisopropylamine (6.2 g) was added and the mixture was stirred at 0-5°C of inner temperature. The precipitated crystals were filtered, washed with diisopropylether and dried to give (2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt(yield 88percent). To a suspension of (2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt (20.0 g) in ethyl acetate (100 ml), was added 20percent aqueous sulfuric acid (16 ml) and the salt was dissolved. The solution was placed after stirring and the organic layer was separated with the aqueous layer. The organic layer was separated with the aqueous layer again after brine was added to the organic solution, and the mixture was stirred and placed. The organic layer was concentrated in vacuo, ethyl acetate (50 ml) and trichloroacetyl chloride (32.3 g) were added to the residue and the mixture was stirred under reflux for 6 hours. The reaction solution was cooled, ethyl acetate (134 ml) was added thereto and it was washed with brine, aqueous solution of sodium bicarbonate, 5percent aqueous sulfuric acid and brine successively. The organic layer was concentrated in vacuo, N-methyl pyrrolidone (26 ml) and ethyl acetate(6.7 ml) were added and the residue was dissolved. The solution was cooled and diisopropylamine (9 g) was added thereto and the mixture was stirred. 4-Bromo-2-fluorobenzylamine (24.2 g) was added dropwise under ice-cooling and the mixture was stirred at 0-5°C for 18 hours. Ethyl acetate (266 ml) was added to the reaction solution and it was washed with 5percent aqueous sulfuric acid, aqueous solution of sodium bicarbonate, 5percent aqueous sulfuric acid and brine successively. The organic layer was concentrated in vacuo, ethanol (100 ml) was added to the residue and it was dissolved under heating to reflux. Ethanol (33 ml) was evaporated, the concentrated solution was cooled with ice-water and the precipitated crystals were filtered and washed with ethanol. The resulting wet crystals were recrystallized from isopropanol (124 ml and 180 ml) twice to give (3R)-2'-(4-bromo-2-fluorobenzyl)spiro[pyrrolidin-3,4'(1'H)-pyrrolo[1,2-a]pyrazin]-1',2,3',5(2'H)-tetraone (yield 58percent).
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