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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   1~35

  • 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.
 

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