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CAS No.: | 147254-64-6 |
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Name: | (3R)-2'-(4-Bromo-2-fluorobenzyl)spiro[pyrrolidine-3,4'-1'H-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2'H)-tetraone |
Article Data: | 6 |
Molecular Structure: | |
Formula: | C17H11 Br F N3 O4 |
Molecular Weight: | 420.194 |
Synonyms: | Spiro[pyrrolidine-3,4'(1'H)-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2'H)-tetrone,2'-[(4-bromo-2-fluorophenyl)methyl]-, (-)-;Spiro[pyrrolidine-3,4'(1'H)-pyrrolo[1,2-a]pyrazine]-1',2,3',5(2'H)-tetrone,2'-[(4-bromo-2-fluorophenyl)methyl]-, (3'R)- (9CI);(3R)-2'-(4-Bromo-2-fluorobenzyl)-1',2',3',4'-tetrahydrospiro[pyrrolidine-3,4'-pyrrolo[1,2-a]pyrazine]-1',2,3',5-tetraone;AS 3201; Ranirestat |
Density: | 1.83g/cm3 |
Melting Point: | 192-193℃ |
Boiling Point: | 702.7°Cat760mmHg |
Flash Point: | 378.8°C |
PSA: | 91.97000 |
LogP: | 1.52790 |
(S)-methyl 4-(2-amino-2-oxoethyl)-2-(4-bromo-2-fluorobenzyl)-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-carboxylate
ranirestat
Conditions | Yield |
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With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; Inert atmosphere; | 95% |
4-bromo-2-fluorobenzylamine
R-(-)-3-ethoxycarbonyl-3-(2-(trichloroacetyl)pyrrol-1-yl)pyrrolidin-2,5-dione
ranirestat
Conditions | Yield |
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In N,N-dimethyl-formamide at 20℃; for 5h; | 71% |
With triethylamine In N,N-dimethyl-formamide at 20℃; | 65% |
With triethylamine In N,N-dimethyl-formamide at 20℃; for 8h; | 65% |
(2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt
4-bromo-2-fluorobenzylamine
ranirestat
Conditions | Yield |
---|---|
Stage #1: (2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt With sulfuric acid; water In ethyl acetate Stage #2: With trifluoroacetyl chloride In ethyl acetate for 6h; Heating / reflux; Stage #3: 4-bromo-2-fluorobenzylamine With water; sodium hydrogencarbonate; diisopropylamine more than 3 stages; | 58% |
R-(-)-3-ethoxycarbonyl-3-(2-(trichloroacetyl)pyrrol-1-yl)pyrrolidin-2,5-dione
ranirestat
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature; | 45% |
(R)-ethyl-3-amino-2,5-dioxopyrrolidine-3-carboxylate
ranirestat
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 72.4 percent / AcOH / 1.5 h / 70 °C 2: 91.9 percent / CHCl3 / 16 h / Heating 3: 45 percent / Et3N / dimethylformamide / 16 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1.1: water / Heating 1.2: 22; 13 / 12 h / 40 °C 2.1: 10 h / 80 °C 3.1: N,N-dimethyl-formamide / 5 h / 20 °C View Scheme |
ethyl 2,5-dioxo-3-(1H-pyrrol-1-yl)pyrrolidine-3-carboxylate
ranirestat
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91.9 percent / CHCl3 / 16 h / Heating 2: 45 percent / Et3N / dimethylformamide / 16 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: ethyl acetate / Reflux 2: triethylamine / N,N-dimethyl-formamide / 8 h / 20 °C View Scheme |
ethyl 3-benzyloxycarbonylamino-2,5-dioxopyrrolidine-3-carboxylate
ranirestat
Conditions | Yield |
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Multi-step reaction with 5 steps 2: 95.9 percent / H2 / 5percent Pd/C / ethanol / 40 - 50 °C / 760 Torr 3: 72.4 percent / AcOH / 1.5 h / 70 °C 4: 91.9 percent / CHCl3 / 16 h / Heating 5: 45 percent / Et3N / dimethylformamide / 16 h / Ambient temperature View Scheme |
(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide
ranirestat
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 95.9 percent / H2 / 5percent Pd/C / ethanol / 40 - 50 °C / 760 Torr 2: 72.4 percent / AcOH / 1.5 h / 70 °C 3: 91.9 percent / CHCl3 / 16 h / Heating 4: 45 percent / Et3N / dimethylformamide / 16 h / Ambient temperature View Scheme |
ethyl (R)-3-hydrazinyl-2,5-dioxopyrrolidine-3-carboxylate hydrochloride
ranirestat
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrogen / nickel / ethanol / 42 h / 20 °C 2.1: water / Heating 2.2: 22; 13 / 12 h / 40 °C 3.1: 10 h / 80 °C 4.1: N,N-dimethyl-formamide / 5 h / 20 °C View Scheme |
ranirestat
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: hydrogenchloride / toluene / 2.5 h / 0 °C 2.1: hydrogen / nickel / ethanol / 42 h / 20 °C 3.1: water / Heating 3.2: 22; 13 / 12 h / 40 °C 4.1: 10 h / 80 °C 5.1: N,N-dimethyl-formamide / 5 h / 20 °C View Scheme |