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Chemical Structure| 79286-79-6 Chemical Structure| 79286-79-6

Structure of 79286-79-6

Chemical Structure| 79286-79-6

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Product Details of [ 79286-79-6 ]

CAS No. :79286-79-6
Formula : C4H10N2
M.W : 86.14
SMILES Code : NC1CCNC1
MDL No. :MFCD00059018

Safety of [ 79286-79-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:2735
Packing Group:

Application In Synthesis of [ 79286-79-6 ]

* 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 [ 79286-79-6 ]

[ 79286-79-6 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 130435-38-0 ]
  • [ 79286-79-6 ]
  • [ 130435-62-0 ]
  • 2
  • 7-Chloro-6-fluoro-1-(2-fluoro-1,1-dimethyl-ethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • [ 79286-79-6 ]
  • [ 130435-91-5 ]
  • 3
  • 6,7-Difluoro-1-(2-fluoro-1-fluoromethyl-1-methyl-ethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester [ No CAS ]
  • [ 79286-79-6 ]
  • [ 130435-65-3 ]
  • 4
  • 7-Chloro-6-fluoro-1-(2-fluoro-1-fluoromethyl-1-methyl-ethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • [ 79286-79-6 ]
  • [ 130435-94-8 ]
  • 5
  • 7-Chloro-6-fluoro-1-(2-fluoro-1,1-bis-fluoromethyl-ethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • [ 79286-79-6 ]
  • [ 130435-97-1 ]
  • 6
  • [ 79286-79-6 ]
  • 7-Chloro-6-fluoro-1-(4-fluoro-phenyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • [ 132195-48-3 ]
  • 7
  • [ 79286-79-6 ]
  • 7-Chloro-6-fluoro-5-methyl-4-oxo-1-pyridin-3-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-5-methyl-4-oxo-1-pyridin-3-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 8
  • [ 79286-79-6 ]
  • 7-Chloro-6-fluoro-5-methyl-4-oxo-1-pyridin-4-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-5-methyl-4-oxo-1-pyridin-4-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 9
  • [ 79286-79-6 ]
  • [ 146560-53-4 ]
  • [ 146560-56-7 ]
  • 10
  • [ 79286-79-6 ]
  • 7-Chloro-6-fluoro-5-methyl-4-oxo-1-(4-trifluoromethyl-phenyl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-5-methyl-4-oxo-1-(4-trifluoromethyl-phenyl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 11
  • [ 79286-79-6 ]
  • 7-Chloro-6-fluoro-1-(4-fluoro-2-methoxy-phenyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • [ 146560-54-5 ]
  • 12
  • [ 79286-79-6 ]
  • 7-Chloro-6-fluoro-1-(2-fluoro-4-methoxy-phenyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • [ 146560-55-6 ]
  • 13
  • [ 79286-79-6 ]
  • 7-Chloro-6-fluoro-5-methyl-4-oxo-1-(4-sulfamoyl-phenyl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-5-methyl-4-oxo-1-(4-sulfamoyl-phenyl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 14
  • [ 79286-79-6 ]
  • 1-(4-Acetylamino-phenyl)-7-chloro-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 1-(4-Acetylamino-phenyl)-7-((S)-3-amino-pyrrolidin-1-yl)-6-fluoro-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 15
  • [ 79286-79-6 ]
  • 7-Chloro-6-fluoro-5-methyl-4-oxo-1-(2,4,6-trifluoro-phenyl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-5-methyl-4-oxo-1-(2,4,6-trifluoro-phenyl)-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 16
  • [ 79286-79-6 ]
  • 7-Chloro-6-fluoro-1-(4-methanesulfonylamino-phenyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 7-((S)-3-Amino-pyrrolidin-1-yl)-6-fluoro-1-(4-methanesulfonylamino-phenyl)-5-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester [ No CAS ]
  • 17
  • [ 79286-79-6 ]
  • [ 108118-77-0 ]
  • [ 177751-67-6 ]
  • 18
  • [ 79286-79-6 ]
  • [ 179740-35-3 ]
  • 1-(3-Amino-4-fluoro-phenyl)-7-((S)-3-amino-pyrrolidin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid [ No CAS ]
  • 19
  • [ 79286-79-6 ]
  • [ 535170-26-4 ]
  • 1-(5-Amino-2-fluoro-phenyl)-7-((S)-3-amino-pyrrolidin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid [ No CAS ]
  • 20
  • [ 79286-79-6 ]
  • [ 179739-64-1 ]
  • [ 179739-88-9 ]
  • 21
  • [ 79286-79-6 ]
  • [ 179739-43-6 ]
  • 1-(3-amino-4,6-difluorophenyl)-7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid [ No CAS ]
  • 22
  • [ 79286-79-6 ]
  • [ 179739-41-4 ]
  • 1-(3-amino-4,6-difluorophenyl)-7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In ethanol; N,N-dimethyl-formamide; EXAMPLE 48 1-(3-amino-4,6-difluorophenyl)-7-[(3S)-3-aminopyrrolidin-1-yl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid To 6,500 mg of N,N-dimethylformamide were added 1,300 mg of 1-(3-amino-4,6-difluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid, 600 mg of <strong>[79286-79-6](3S)-3-aminopyrrolidine</strong>, and 1,000 mg of triethylamine. The solution was stirred at 90 C. for 1 hour. The reaction solution was allowed to cool down, combined with 25 ml of ethanol, heated at reflux for 5 minutes, and allowed to cool down. The precipitate was collected by filtration and washed with ethanol and then with diisopropyl ether to give 1,410 mg of the title compound.
  • 23
  • [ 79286-79-6 ]
  • [ 179739-45-8 ]
  • 1-(5-Amino-2,4-difluoro-phenyl)-7-((S)-3-amino-pyrrolidin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid [ No CAS ]
  • 24
  • [ 79286-79-6 ]
  • [ 179739-47-0 ]
  • 7-((S)-3-Amino-pyrrolidin-1-yl)-1-(5-amino-2,3,4-trifluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid [ No CAS ]
  • 25
  • [ 79286-79-6 ]
  • [ 179740-21-7 ]
  • 1-(5-Amino-2,4-difluoro-phenyl)-7-((S)-3-amino-pyrrolidin-1-yl)-8-chloro-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid [ No CAS ]
  • 26
  • [ 79286-79-6 ]
  • [ 240813-70-1 ]
  • (S)-2-(3-Amino-1-pyrrolidinyl)-N-(2-chloro-6-methylphenyl)imidazo[1,5-a]pyrido[3,2-e]pyrazin-6-amine [ No CAS ]
  • 27
  • 1-[(4-methoxyphenyl)methyl]-2-oxo-3-{1-[(trifluoromethyl)sulfonyl]benzimidazol-2-yl}-6-chloro-4-hydroquinolyl(trifluoromethyl)sulfonate [ No CAS ]
  • [ 79286-79-6 ]
  • Trifluoro-methanesulfonic acid 2-[6-chloro-1-(4-methoxy-benzyl)-2-oxo-4-((S)-pyrrolidin-3-ylamino)-1,2-dihydro-quinolin-3-yl]-benzoimidazol-1-yl ester [ No CAS ]
  • 28
  • [ 79286-79-6 ]
  • [ 407-25-0 ]
  • 2,2,2-Trifluoro-N-[(S)-1-(2,2,2-trifluoro-acetyl)-pyrrolidin-3-yl]-acetamide [ No CAS ]
  • 29
  • [ 403-33-8 ]
  • [ 79286-79-6 ]
  • [ 953435-47-7 ]
YieldReaction ConditionsOperation in experiment
65% With potassium carbonate; In dimethyl sulfoxide; at 130℃; for 18h; Example 37a; (S)-N-(4-Aminobiphenyl-3-yl)-4-(3-aminopyrrolidin-l-yl)benzamide (327); Scheme 37; Step 1 : (SVMethyl 4-(3-aminopyrrolidin-l-v0benzoate (323); [0940] K2CO3 (7.71 g, 55.84 mmol) was added to a solution of (S)-pyrrolidin-3 -amine (5.0 g,58.04 mmol) and methyl 4-fluorobenzoate (8.6 g, 55.81 mmol) in DMSO (20 mL). The reaction mixture was stirred for 18 h at 130 0C in a sealed tube. The reaction mixture was cooled, diluted with AcOEt and H2O, and extracted with AcOEt (3 times). The extract was washed with water,NH4Cl and brine, dried over MgSO4, filtered and concentrated to give the title compound 323(7.98 g, 65% yield) as a pink solid.[0941] 1H NMR (DMSO-de) delta (ppm): 7.75 (d, J = 9.0 Hz, 2H), 6.52 (d, J = 9.0 Hz, 2H), 3.74(s, 3H), 3.60-3.55 (m, IH), 3.45-3.41 (m, 2H), 3.32-3.25 (m, IH), 2.97-2.93 (m, IH), 2.09-2.01(m, IH), 1.72-1.68 (m, IH). LRMS calc. 220.1; found 221.1 (MH)+.
  • 30
  • [ 959431-70-0 ]
  • [ 79286-79-6 ]
  • 5-Bromo-3-[2-propyl-6-((S)-pyrrolidin-3-ylamino)-2H-pyrazolo[3,4-d]pyrimidin-4-yl]-1,3-dihydro-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In ethanol; at 130℃; for 0.166667h;AMicrowave irradiation; EXAMPLE 362; 5-Bromo-3-[2-propyl-6-((S)-pyrrolidin-3-ylamino)-2H-pyrazolo[3,4-d]pyrimidin-4-yl]-1,3-dihydro-indol-2-one; Example 188 (40 mg, 0.0983 mmol) and (S)-(-)-3-aminopyrrolidine (87 muL, 0.983 mmol) were heated in 1 mL EtOH at 130 C. in microwave for 10 min. Upon cooling, the product precipitated in the reaction tube. The resulting solid was filtered and pumped dry to afford 44 mg (98%) of a yellow solid. mp 315-320 C.; MS (ES+calculated: 456.35; found: 456.63, 457.79 M+H). HPLC (99%) purity, retention time 3.40 minutes-Method C); 1H NMR (400 MHz, DMSO-d6) delta 9.70 (s, 1H), 9.40 (s, 1H), 8.55 (s, 1H), 6.86 (d, J=8 Hz, 1H), 6.61 (d, J=8 Hz, 1H), 5.9 (br s, 2H), 4.11 (t, J=7 Hz, 2H), 3.77 (br s, 2H), 3.70 (br s, 2H), 3.43 (m, 2H), 2.18 (m, 1H), 1.86 (m, 4H), 1.07 (m, 2H), 0.85 (t, J=7 Hz, 3H).
  • 31
  • [ 23095-31-0 ]
  • [ 79286-79-6 ]
  • [ 956468-08-9 ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine; In dichloromethane; for 2h; To a solution of (3S)-3- aminopyrrolidine (237 mg, 2.75 mmol) and thethylamine (843 uL, 6.05 mmol) in 9 ml_ DCM was added 3,4-bis(methyloxy)benzenesulfonyl chloride (1.27 g, 5.36 mmol). After stirring for 2 h, the reaction solution was diluted with 1 N HCI. The organic phase was separated, dried over Na2SO4, filtered and concentrated in vacuo. The desired product was afforded as a foam (560 mg, 65% yield). LCMS (M+H = 487.2). 1H NMR (DMSO-d6, 400MHz) delta : 7.73 (1 H, d), 7.30 (1 H, dd), 7.28 (1 H, dd), 7.23 (1 H, d), 7.10-7.14 (2 H, m), 7.08 (1 H, d), 3.83 (3 H, s), 3.81 (3 H, s), 3.80 (3 H, s), 3.77 (3 H, s), 3.36 (1 H, sep), 3.12-3.20 (2 H, m), 3.06 (1 H, m), 2.88 (1 H, m), 1.70 (1 H, m), 1.48 (1 H, m).
  • 32
  • [ 852329-46-5 ]
  • [ 79286-79-6 ]
  • [ 852330-33-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl acetamide; at 70℃; Step 9E: To the solution of compound 4a (16.0 g, 43. 8 mmol) in DMA (150 mL) was added (S) -pyrrolidin-3-ylamine (4.1 g, 48.2 mmol) and TEA (30.7 mL, 219 mmol). The reaction mixture was heated in a pressure vessel at 70 C overnight. The solvent was removed at reduced pressure and the residue was dissolved in DCM-isoPrOH (3: 1, 800 mL), washed well with 1 N NaOH (5x 100 mL), brine (2x 100 mL) and dried over MgS04 then concentrated at reduced pressure. Crystallization with ether-hexanes afforded compound 9e (10.0 g), LC/MS: 313.2 [M+H] +. To compound 9d resulting from the previous step in ethanol (80 mL) was added compound 9e (6.44 g, 21.2 mmol). The reaction mixture was stirred in a pressure vessel at 90C for 2 days, monitored by LC/MS. The reaction mixture was subjected to rotary evaporation to remove solvent. The resulting residual was dissolved in 800 mL DCM, washed with 10% NaHS04, saturated NaHCO3 solution, and brine ; dried over MgS04, filtered and concentrated under reduced pressure to give an orange oil. The crude product was purified by silica gel column chromatography (from 0% MeOH in DCM to 2% MeOH in DCM) to afford 9f (3. 0g). LC/MS: 526.1 [MH] +.
  • 33
  • [ 114715-38-7 ]
  • [ 79286-79-6 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen; In methanol; at 70℃; under 7500.75 Torr; for 8h; 7.0 g of the (S)-1-benzyl-3-aminopyrrolidine, 25 ml of methanol, and 0.7 g of 5% Pd/C were introduced into a 100 ml autoclave, and hydrogen was adjusted to have a pressure of 1 MPa. The temperature was increased to 70 C. and stirring was performed for 8 hours. After the reaction was complete, the temperature was decreased to room temperature and the pressure was released. The content was filtered and the mother liquor was concentrated and distilled, and thus 3.2 g of (S)-3-aminopyrrolidine were obtained as the distillate collected at 80 to 83 C./40 kPa. As a result of analysis, the chemical purity was 99% and the optical purity was 90% e.e.
91% With hydrogen;5% palladium over charcoal; In water; at 80℃; for 8h; A 500 ml four-neck flask equipped with a stirrer, a thermometer, a Dimroth condenser, and a gas introduction pipe was loaded with (S)-3-amino-1-benzylpyrrolidine 52.5 g (0.3 mole, optical purity 99.5%/ee), water 97.5 g, and 5% Pd/C 5.25 g (PE type, 55.27% water content, manufactured by N. E. Chemcat Corp.), and while the contents being stirred at 80C, hydrogen was ventilated for 8 hours. After hydrogen ventilation was stopped, the mixture was cooled to a room temperature while being stirred and the catalyst was separated by vacuum filtration. The filtrate was vacuum concentrated to about 50 g by an evaporator. The concentrated product was distilled by a distillation apparatus equipped with about 5-step refining distillation towers packed with Heli-pack to obtain (S)-3-aminopyrraiidine 23.6 g as a fraction at 4.8 kPa. The yield was 91.0% and the chemical purity was 99.9 area% and an optical purity was 99.5%ee.
  • 34
  • [ 346597-03-3 ]
  • [ 79286-79-6 ]
  • [ 749844-54-0 ]
YieldReaction ConditionsOperation in experiment
41% In DMF (N,N-dimethyl-formamide); isopropyl alcohol; at 130℃; for 10h;Heating in a microwave oven, 300W; 7-(2-Bromobenzyl)-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (10A) (100 mg, 0.26 mmol) and (S)-(-)-3-aminopyrrolidine (112 mg, 1.30 mmol) were dissolved in 2-propanol (20 ml) and DMF (5 ml) and subjected to microwaves (method F, 130 C., 300W) for 10 hours. The solvents were evaporated and the crude product was purified by preparative HPLC (method A1, Rt=6.92 min.) to give the title compound as brown crystals.
  • 35
  • [ 346597-03-3 ]
  • [ 79286-79-6 ]
  • [ 485820-45-9 ]
YieldReaction ConditionsOperation in experiment
41% In DMF (N,N-dimethyl-formamide); isopropyl alcohol; at 130℃;Microwaves; [7- (2-BROMOBENZYL)-8-CHLORO-1, 3-DIMETHYL-3,] 7-dihydropurine-2,6-dione [(10A)] (100 mg, 0.26 [MMOL)] and [(S)- (-)-3-AMINOPYRROLIDINE] (112 mg, 1.30 [MMOL)] were dissolved in 2- propanol (20 [ML)] and DMF (5 ml) and subjected to microwaves (method F, [130C,] [300W)] for 10 hours. The solvents were evaporated and the crude product was purified by preparative HPLC (method [A1,] Rt = 6.92 min. ) to give the title compound as brown crystals. Yield : 50 mg [(41%).] Mp. [215-217C.] 'H-NMR [(MEOD,] 200 MHz) 8 : 2. 04 (m, [1 H),] 2.33 (m, [1 H),] 3.25 (s, 3H), 3.48-3. 78 (m, 6H), 3.90 (m, 2H), 5.53 (d, [1 H),] 5.60 (d, [1 H),] 6.80 (dd, 1 H), 7.25 (m, 2H), 7.63 (dd, 1H). HPLC-MS (Method B): m/z = 433 (M+), Rt = 1.80 min.
  • 36
  • [ 24424-99-5 ]
  • [ 79286-79-6 ]
  • [ 99724-19-3 ]
  • [ 147081-44-5 ]
YieldReaction ConditionsOperation in experiment
0.4%; 81.7% With potassium hydroxide; In methanol; at 15 - 20℃; for 1h;pH 11.8 - 12.2; 60 g of methanol and 8.6 g (0.1 mols) of (S)-3-aminopyrrolidine (Chemical purity 99.8 %, optical purity 99.5 % ee - hereinafter referred to as S-AP) were fed into a 200-ml 4-neck flask equipped with a stirrer, a pH sensor and two strapped dropping funnels, and stirred at 15 to 20C. 21.8 g (0.1 mols) of di-tertiary butyl dicarbonate (by Tokyo Chemical) was fed into it via one dropping funnel, and 25 g (0.11 mols) of methanolic solution of 25 % potassium hydroxide was thereinto via the other dropping funnel. With stirring at 15 to 20C, di-tertiary butyl dicarbonate was dropwise added to the reaction system over a period of about 1 hour. During this, the methanolic solution of 25 % potassium hydroxide was dropwise added thereto so as to make the reaction system have a pH of from 11.8 to 12.2. The reaction mixtures were analyzed for its composition, and it comprised 4 % of the starting 3-aminopyrrolidine, 86.7 % of the product, 3-amino-1-tertiary butoxycarbonylpyrrolidine (hereinafter referred to as 1-BocAP), and 8.4 % of 1-tertiary butoxycarbonyl-3-tertiary butoxycarbonylaminopyrrolidine (hereinafter referred to as DiBocAP). After the reaction, the reaction mixtures were concentrated under reduced pressure to make 32 g. 100 g of toluene was added to the concentrated solution, and inorganic salts were precipitated with stirring. The precipitated crystals were filtered away, and the filtrate was distilled under reduced pressure to obtain a fraction at 120 to 125C/0.7 kPa, (S)-3-amino-1-tertiary butoxycarbonylpyrrolidine. Its weight was 15.2 g, and its yield was 81.7 %. (Chemical purity 99.1 %; optical purity 99.5 % ee. ) The positional isomer, 3-tertiary butoxycarbonylaminopyrrolidine was 0.4 %.
  • 37
  • [ 305334-58-1 ]
  • [ 79286-79-6 ]
  • 1-[(3S)-aminopyrrolidin-1-yl]-2-ethyl-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With triethylamine; In DMF (N,N-dimethyl-formamide); at 80℃; for 17h; To N,N-dimethylformamide (15 ml) suspension of 500 mg (1.85 mmol) of 1-chloro-2-ethyl-3-methylpyrido[1,2-a]benzimidazole-4-carbonitrile (No.I-2) were added 239 mg (2.78 mmol) of (3S)-aminopyrrolidine and 774 mul (5.55 mmol) of triethylamine. The system was replaced with nitrogen and sealed up, and heated at 80C for 17 hours. After cooling, the solvent was evaporated under reduced pressure, the residue was dissolved in 30 ml of chloroform, and the solution was washed with 20 ml of saturated sodium bicarbonate solution. The aqueous layer was extracted with chloroform (30 ml × 3), and the combined chloroform layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was applied to a silica gel column chromatography. This was eluted with a mixed solvent of di chloromethane/methanol (10/1, v/v) to obtain a crude product of the entitled compound. This was recrystallized from ethanol to obtain 316 mg (54 %) of the entitled compound (No.96) as a yellow crystal. MS(EI)m/z:320(M+).1H-NMR(400MHz, CDCl3)delta: 1.30(3H, t, J=7.57Hz), 1.94-2.08(1H, m), 2.36-2.52(1H, m), 2.60-2.96(2H, m), 2.71(3H, s), 3.00-3.88(4H, m), 4.00-4.11(1H, m), 7.29-7.39(1H, m), 7.48-7.58(1H, m), 7.90-8.05(1H, m), 7.99(1H, d, J=8.30Hz). IR(ATR): 2220, 1628, 1593, 1498, 1479, 1442, 1408, 1306 cm-1.
  • 38
  • [ 577775-46-3 ]
  • [ 79286-79-6 ]
  • 1-[(3S)-aminopyrrolidin-1-yl]-3-methyl-2-phenylpyrido[1,2-a]benzimidazole-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With triethylamine; In DMF (N,N-dimethyl-formamide); at 80℃; for 16h; 395 mul (2.83 mmol) of triethylamine and 99 mul (1.13 mmol) of (3S)-aminopyrrolidine were added to N,N-dimethylformaldehyde (10 ml) suspension of 300 mg (944 mumol) of 1-chloro-3-methyl-2-phenylpyrido[1,2-a]benzimidazole-4-carbonitrile (I-8). The system was replaced with nitrogen and sealed up, and heated at 80C for 16 hours. After cooling, the solvent was evaporated under reduced pressure, the residue was dissolved in chloroform, washed with aqueous saturated sodium bicarbonate solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography. From the eluate with dichloromethane/methanol (20/1, v/v), a crude product of the entitled compound was obtained, and this was washed with diisopropyl ether and was collected by filtration to obtain 146 mg (42 %) of the entitled compound as a yellow crystal. MS(ESI)m/z:368(M+1)+.1H-NMR(CDCl3)delta: 1.80-2.35(2H, m), 2.31(3H, s), 2.72-3.80(5H, m), 7.20-7.30(2H, m), 7.33(1H, t, J=7.3Hz), 7.47-7.59(4H, m), 7.97-8.05(1H, m), 8.01(1H, d, J=8.3Hz). IR(ATR) : 2222, 1624, 1589, 1466, 1441, 1408, 1373, 1300 cm-1.
  • 39
  • [ 815631-33-5 ]
  • [ 79286-79-6 ]
  • C2HF3O2*C28H33F7N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Experimental Procedure for Examples 54-123 (Table 2):; The compounds listed in Table 2 were prepared from Intermediate 24. The amines for sidechain "Z" (0.2 mmol, 4.0 eq) were pre-weighed in 1 dram, septa-capped vials. The aldehyde (0.05 mmol, 1.0 eq) was dissolved in 1 mL of anhydrous THF and added to the reaction vials and the resulting solutions shaken at rt for 16 h. To each reaction vial was thenadded Na(OAc)3BH (30.00 mg, 2.5 eq) and the vials were shaken and addtitional 4.5 h. The reactions were quenched by adding 1N NaOH and 2.25 mL EtOAc. The organics were separated and loaded onto an equilibrated SCX SPE (conditioned with 5 mL MeOH, 2x 5 mL EtOAc) columns. The desired products were then eluted off using 1N TEA in MeOH (5mL). These solutions were collected in tared vials and dried under a N2 stream. Purifications were accomplished by HPLC separation on a Waters Symmetry C18 column (5mm, 3.9 x 150 mm) with a 1.0 mL/min flow rate eluting with a gradient system of 100%, 80%, 0% (0.1% TFA in *(H2O/CH3CN) injecting each sample in 2 mL of solvent. Isolated and tested as the TFA salts.
  • 40
  • [ 447-61-0 ]
  • [ 79286-79-6 ]
  • [ 820985-21-5 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; for 24h;Heating / reflux; 3 (S)-Pyrrolidin-3-amine (0.45g, 5.2mmol) and trifluoromethylbenzaldehyde (0.87g, 5. 0MMOL), a crystal of 4-toluenesulphonic acid and toluene were refluxed with stirring for one day, using a Dean and Stark apparatus. The solution was evaporated in vacuo to give the title compound as a brown oil (M+H = 243).
With toluene-4-sulfonic acid; toluene; for 24h;Heating / reflux; 3 (S)-PYRROLIDIN-3-AMINE (0.45g, 5.2mmol) and trifluoromethylbenzaldehyde (0. 87G, 5. 0MMOL), a crystal of 4-toluenesulphonic acid and toluene were refluxed with stirring for one day, using a Dean and Stark apparatus. The solution was evaporated in vacuo to give the title compound as a brown oil (M+H = 243).
With toluene-4-sulfonic acid; In toluene; for 24h;Heating / reflux; 3 (S)-PYRROLIDIN-3-AMINE (0.45g, 5.2mmol) and TRIFLUOROMETHYLBENZALDEHYDE (0.87g, 5. 0MMOL), a crystal of 4-toluenesulphonic acid and toluene were refluxed with stirring for one day, using a Dean and Stark apparatus. The solution was evaporated in vacuo to give the title compound as a brown oil (M+H = 243).
With toluene-4-sulfonic acid; In toluene; for 24h;Heating / reflux; 3 (S)-Pyrrolidin-3-amine (0.45g, 5. 2mmol) and trifluoromethylbenzaldehyde (0.87g, 5. 0mmol), a crystal of 4-toluenesulphonic acid and toluene were refluxed with stirring for one day, using a Dean and Stark apparatus. The solution was evaporated in vacuo to give the title compound as a brown oil (M+H = 243).

  • 41
  • [ 447-61-0 ]
  • [ 79286-79-6 ]
  • [ 820985-23-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;5%-palladium/activated carbon; In ethanol; under 3102.97 Torr; for 3h; A mixture of 3 (S)-pyrrolidin-3-amine (4g, 46. 5mmol), 2-trifluoromethylbenzaldehyde (9. 1g, 46. 5mmol), 5% palladium on carbon (0.4g) and ethanol (150mL) was hydrogenated at 60psi for 3 hours using a Parr hydrogenator. The catalyst was filtered off and the filtrate evaporated in vacuo to give the title compound as an oil. MS: [M+H] = 245.
With hydrogen;5%-palladium/activated carbon; In ethanol; under 3102.97 Torr; for 3h; A mixture of 3 (S)-pyrrolidin-3-amine (4g, 46. 5MMOL), 2-trifluoromethylbenzaldehyde (9. 1g, 46. 5MMOL), 5% palladium on carbon (0.4g) and ethanol (150ML) was hydrogenated at 60psi for 3 hours using a Parr hydrogenator. The catalyst was filtered off and the filtrate evaporated in vacuo to give the title compound as an oil. MS: [M+H] = 245.
With hydrogen;5%-palladium/activated carbon; In ethanol; under 3102.97 Torr; for 3h; A mixture of 3(S)-pyrrolidin-3-amine (4g, 46. 5MMOL), 2-trifluoromethylbenzaldehyde (9. 1g, 46. 5MMOL), 5% palladium on carbon (0.4g) and ethanol (150mL) was hydrogenated at 60psi for 3 hours using a Parr hydrogenator. The catalyst was filtered off and the filtrate evaporated in vacuo to give the title compound as an oil. MS: [M+H] = 245.
With hydrogen;palladium on activated carbon; In ethanol; under 3102.97 Torr; for 3h; A mixture of 3(S)-pyrrolidin-3-amine (4g, 46. 5MMOL), 2-trifluoromethylbenzaldehyde (9. 1g, 46. 5MMOL), 5% palladium on carbon (0.4g) and ethanol (150mL) was hydrogenated at 60psi for 3 hours using a Parr hydrogenator. The catalyst was filtered off and the filtrate evaporated in vacuo to give the title compound as an oil. MS: [M+H] = 245.

  • 42
  • [ 803736-57-4 ]
  • [ 79286-79-6 ]
  • [ 803735-62-8 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 100℃; for 0.666667h;Microwave heating; A stirred suspension of 2, 6-dichloro-N (cyclohexylmethyl) quinoline-5-carboxamide (Example 43 (a) ) (500 mg) and (3S)-3-pyrrolidinamine (0.60 mL) in acetonitrile (3 ML) was heated at 100C in a microwave for 40 minutes after which it was cooled to room temperature and concentrated. Purification by chromatography (SI02, dichloromethane: methanol: ammonia in methanol (7 M) 95: 5: 0.5 as eluant) and subsequent recrystallisation (acetonitrile) afforded the title compound as a solid (280 mg). 1H NMR (400 MHz, DE-DMSO, 90C) 6 8.26 (1H, BR S), 7.74 (1H, d), 7.51 (1H, d), 7.44 (1H, d), 6.90 (1H, d), 3.72-3. 59 (3H, m), 3.58-3. 49 (1H, m), 3.26-3. 16 (3H, m), 2. 15-2. 06 (1H, m), 1.83-1. 56 (7H, m), 1.30-1. 12 (3H, m), 1.08-0. 96 (2H, m). MS: APCI (+ve) 387/389 (M+H+).
  • 43
  • [ 803736-95-0 ]
  • [ 79286-79-6 ]
  • N-[2-((3S)-3-amino-1-pyrrolidinyl)-6-chloro-5-quinolinyl]-3-cyclohexanepropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In acetonitrile; at 100℃; for 1h;Microwave heating; N (2, 6-DICHLORO-5-QUINOLINYL)-CYCLOHEXANEPROPANAMIDE (Example 90 (a) ) (0.24 g), (S)-3- AMINOPYRROLIDINE (0. 18 g) and triethylamine (0.1 mL) were suspended in acetonitrile and heated at 100C in a microwave for 1 hour. The resulting precipitate was filtered and then washed with acetonitrile to give a brown solid. Purification (SI02, methanol: dichloromethane: triethylamine 3: 97: 0.5) gave the title compound as a colourless solid (230 mg). 1H NMR (400 MHz, DMSO) 6 9.77 (1H, s), 7.86-7. 83 (1H, d), 7.56-7. 54 (1H, d), 7.48- 7.46 (1H, d), 6.93-6. 91 (1H, d), 3.70-3. 64 (3H, m), 3.56-3. 55 (1H, m), 2.46-2. 42 (2H, t), 2.16-2. 14 (1H, m), 1.85-1. 53 (8H, m), 1. 32-1. 1 (5H, m), 0.96-0. 85 (2H, m). MS: APCI (+ve) 401.2 (M+H+)
  • 44
  • [ 836612-26-1 ]
  • [ 79286-79-6 ]
  • (βR)-N-[2-[(3S)-3-amino-1-pyrrolidinyl]-6-chloro-5-quinolinyl]-β-methyl-benzenepropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In acetonitrile; at 100℃; for 1h;Microwave irradiation; Example 13 (ssR)-N-[2-[(3S)-3-AMINO-1-PYRROLIDINYL]-6-CHLORO-5-QUINOLINYL]-ss-METHYL- benzenepropanamide To a 10 mL microwave vial was added (R)-N-(2, 6-DICHLORO-5-QUINOLINYL)--METHYL- benzenepropanamide (Example 3 (b) ) (200 mg), (3S)-3-PYRROLIDINAMINE (145 mg), triethylamine (0.085 mL) and acetonitrile (5 mL). The vial was sealed and heated at 100C for 1 hour within a microwave. The reaction was cooled to room temperature and evaporated. Purification (SI02, methanol: dichloromethane: ammonium hydroxide solution 10: 90: 1 as eluant) afforded the title compound as a solid (80 mg). 'H NMR (400 MHz, d6-DMSO) 5 9.77 (1H, s), 7.51 (1H, d), 7.43 (1H, d), 7.39-7. 30 (5H, M), 7.29-7. 23 (1H, m), 6.71 (1H, d), 3.69-3. 46 (4H, M), 3.38-3. 26 (1H, M), 3.24-3. 14 (1H, m), 2.77 (1H, dd), 2.67 (1H, dd), 2.12-2. 01 (1H, M), 1.78-1. 68 (1H, M), 1.33 (3H, d). MS: APCI (+ve) 409/411 (M+H+). m. p. 204-207C
  • 45
  • 7-chloro-1-(3-ethoxycarbonylamino-4,6-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid [ No CAS ]
  • [ 79286-79-6 ]
  • 7-[(3S)-3-aminopyrrolidin-1-yl]-1-(3-ethoxycarbonylamino-4,6-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; N,N-dimethyl-formamide; EXAMPLE 138 7-[(3S)-3-aminopyrrolidin-1-yl]-1-(3-ethoxycarbonylamino-4,6-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid To 350 mul of N,N-dimethylformamide were added 68 mg of 1-(3-ethoxycarbonylamino-4,6-difluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid and 70 mg of <strong>[79286-79-6](3S)-3-aminopyrrolidine</strong>. The solution was stirred at 80 C. for 20 minutes. Then 0.5 ml of ethanol was added. The reaction solution was allowed to cool down whereupon the precipitate was collected by filtration and washed with ethanol and then diisopropyl ether to give 73 mg of the title compound.
  • 46
  • [ 189279-53-6 ]
  • [ 79286-79-6 ]
  • 1-(6-amino-3,5-difluoropyridin-2-yl)-7-[(3S)-3-aminopyrrolidin-1-yl]-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; N,N-dimethyl-formamide; EXAMPLE 8 Synthesis of 1-(6-amino-3,5-difluoropyridin-2-yl)-7-[(3S)-3-aminopyrrolidin-1-yl]-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid To 250 mg of N,N-dimethylformamide were added 60 mg of 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and 60 mg of <strong>[79286-79-6](3S)-3-aminopyrrolidine</strong>, and the mixture was heated under reflux with stirring at 90 C. for 1 hour. After adding 1 ml of ethanol, the mixture was allowed to cool, and the precipitate was collected by filtration and washed with ethanol and diisopropylether successively to obtain 41 mg of the title compound as a pale brown powder. Melting point: 248 to 250 C. (decomposed) 1 H-NMR (d6 -DMSO) delta; 1.73 (m, 1H), 2.03 (m, 1), 4.67 (m, 2H), 6.75 (brs, 2H), 7.95 (t, J=9 Hz, 1H), 7.98 (d, J=14 Hz, 1H), 8.73 (s, 1H) (Part of signals overlapped with the proton of water, and were undistinguishable.)
  • 47
  • ethyl 1-(1-chloroprop-2-yl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate [ No CAS ]
  • [ 79286-79-6 ]
  • ethyl (3S)-7-(3-aminopyrrolidinyl)-1-(1-chloroprop-2-yl)-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; Reference Example 5 Ethyl (3S)-7-(3-aminopyrrolidinyl)-1-(1-chloroprop-2-yl)-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 660 mg (2 mmol) of ethyl 1-(1-chloroprop-2-yl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate and 414 mg (4.8 mmol) of 3S-(-)-3-aminopyrrolidine were dissolved in 40 ml of acetonitrile and the mixture was heated under refluxing for 4 hours. After the reaction, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform: methanol:aqueous ammonia=300:6:1) to obtain 465 mg of light yellow crystal of ethyl (3S)-7-(3-aminopyrrolidinyl)-1-(1-chloroprop-2-yl)-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate. mp. 149-152 C. IR (KBr): 3415, 1712, 1625, 1512 cm-1.
  • 48
  • [ 79286-79-6 ]
  • [ 147082-06-2 ]
  • (2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium chloride; 1,1'-carbonyldiimidazole; In acetonitrile; 23(i) (2S,4S)-4-(4-Methoxybenzylthio)-2-[(3S)-3-aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 2.92 g of N,N'-carbonyldiimidazole were added to a solution of 6.70 g of (2S,4S)-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)-2-pyrrolidinecarboxylic acid in 50 ml of dry acetonitrile, and the resulting mixture was stirred at room temperature for 1 hour. A solution of 1.55 g of <strong>[79286-79-6](3S)-3-aminopyrrolidine</strong> in 10 ml of dry acetonitrile was then added to the mixture, whilst ice-cooling, and the mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with water and with an aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 4.10 g of the title compound, as a powder. Infrared Absorption Spectrum (KBr), numax cm-1: 1708, 1651, 1609, 1512, 1440, 1404, 1346, 1248, 1174.
YieldReaction ConditionsOperation in experiment
The residue is distilled under reduced pressure to give (3S)-3-aminopyrrolidine (0.4 g). b.p. 70-72 C./40 mmHg [alpha]D20 +9.0 (c=1, H2 O)
  • 50
  • [ 56440-28-9 ]
  • [ 79286-79-6 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; REFERENCE EXAMPLE 2 Preparation of (3S)-3-aminopyrrolidine: (3S)-3-Amino-2-pyrrolidone hydrochloride (1.5 g) [cf. Beilsteins Handbuch der Organischen Chemie, Drittes und Viertes Erganzungswerk, issued in 1980, page 6401] is suspended in diethyl ether (50 ml), and to the suspension is added lithium aluminum hydride (1.0 g), and the mixture is refluxed with stirring for 48 hours. While stirring under ice cooling, a small amount of ice is added to the reaction mixture to decompose excess lithium aluminum hydride, and the insoluble materials are removed by filtration. The filtrate is dried over anhydrus sodium sulfate, and distilled under reduced pressure to remove diethyl ether. The residue is distilled and fractions of 30-100 C./25 mmHg are collected to give crude (3S)-3-aminopyrrolidine (216 mg) as an oily substance. [alpha]D20 -6.9 (c=1, H2 O) The above crude (3R)-3-aminopyrrolidine is purified in the form of L(+)-tartrate as follows.
  • 51
  • [ 280-57-9 ]
  • [ 93107-30-3 ]
  • [ 79286-79-6 ]
  • [ 90-02-8 ]
  • 7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-3-quinolinecarboxylic acid hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; hydrogenchloride; ethanol; water; acetonitrile; EXAMPLE 8 STR50 1.34 g 11 mmol) of salicylaldehyde are added to 0.86 g (10 mmol) of 3-aminopyrrolidine, the mixture is stirred at room temperature for about 10 minutes and the viscous reaction product is dissolved in a mixture of 20 ml of acetonitrile and 10 ml of dimethylformamide. After addition of 2.2 g (20 mmol) of 1,4-diazabicyclo[2.2.2]octane and 2.65 g (10 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, the mixture is heated under reflux for 1 hour and cooled, and the reaction product which has crystallized out is filtered off with suction, washed with acetonitrile and dissolved in 30 ml of half-concentrated hydrochloric acid. The solution is concentrated, the residue is stirred with acetonitrile, the undissolved material is dissolved in 30 ml of water under the influence of heat, the solution is filtered and 100 ml of ethanol are added to the filtrate. The hydrochloride which has precipitated is filtered off with suction, washed with ethanol and dried. Yield: 2.6 g (70.7percent of theory) of 7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-3-quinolinecarboxylic acid hydrochloride; melting point: 310° C.-317° C. (with decomposition). The reaction proceeds in an analogous manner if benzaldehyde, 2-chlorobenzaldehyde, 3-chlorobenzaldehyde, 2,4-dichlorobenzaldehyde, 2-methylbenzaldehyde, 4-methylbenzaldehyde, 4-chlorobenzaldehyde, 4-fluorobenzaldehyde or 3,4-difluorobenzaldehyde is used instead of the salicylaldehyde.
  • 52
  • [ 166816-33-7 ]
  • [ 79286-79-6 ]
  • [ 166816-34-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In hydrogenchloride; diethyl ether; acetonitrile; Example 4 Synthesis of 7-{3(S)-aminopyrrolidin-1-yl}-6-fluoro-1-(isoxazol-3-yl)-1,4-dihydro-4-oxoquinoline-3- carboxylic acid hydrochloride (Compound No. 4) In 5 ml of acetonitrile, 50 mg of Compound No. 3 were suspended. To the resulting suspension, 23 mg of 3-(S)-aminopyrrolidine and 41 mg of triethylamine were added, followed by stirring at 80 C for one hour. The precipitate so obtained was collected by filtration, washed with ethanol and then dissolved in 6N hydrochloric acid to obtain its hydrochloride. The solvent was distilled off. The residue was then suspended in diethyl ether, followed by collection through filtration, whereby 64 mg of the title compound was obtained as a pale yellow solid.
  • 53
  • 6,7-difluoro-1-(5-methylisoxazol-3-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid [ No CAS ]
  • [ 79286-79-6 ]
  • [ 166817-16-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In hydrogenchloride; diethyl ether; acetonitrile; Example 36 Synthesis of 7-{3(S)-aminopyrrolidin-1-yl}-6-fluoro-1-(5-methylisoxazol-3-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride (Compound No. 86) In 5 ml of acetonitrile, 50 mg of Compound No. 85 were dissolved. To the resulting mixture, 18 mg of 3(S)-aminopyrrolidine and 42 mg of triethylamine were added, followed by stirring at 80C for one hour. The precipitate so obtained was collected by filtration, washed with ethanol, and the dissolved in 6N hydrochloric acid to obtain its hydrochloride. The solvent was distilled off. The residue was suspended in diethyl ether, followed by collection through filtration, whereby 59 mg of the title compound was obtained as a pale yellow solid.
  • 54
  • 6,7-difluoro-1-(3-methylisoxazol-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid [ No CAS ]
  • [ 79286-79-6 ]
  • [ 166817-23-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In hydrogenchloride; diethyl ether; acetonitrile; Example 43 Synthesis of 7-{3(S)-aminopyrrolidin-1-yl}-6-fluoro-1-(3-methylisoxazol-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride (Compound No. 93) In 55 ml of acetonitrile, 50 mg of Compound No. 92 were dissolved. To the resulting solution, 17 mg of 3(S)-aminopyrrolidine and 37 mg of triethylamine were added, followed by stirring at 80C for one hour. The precipitate so obtained was collected by filtration, washed with ethanol and then dissolved in 6N hydrochloric acid to obtain its hydrochloride. The solvent was distilled off. The residue was suspended in diethyl ether, followed by collection through filtration, whereby 58 mg of the title compound was obtained as a pale yellow solid.
 

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