Home Cart 0 Sign in  

[ CAS No. 2364554-48-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2364554-48-1
Chemical Structure| 2364554-48-1
Structure of 2364554-48-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 2364554-48-1 ]

Related Doc. of [ 2364554-48-1 ]

Alternatived Products of [ 2364554-48-1 ]

Product Details of [ 2364554-48-1 ]

CAS No. :2364554-48-1 MDL No. :MFCD34602690
Formula : C18H19N5O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 337.38 Pubchem ID :-
Synonyms :
CK-274;CK-3773274

Safety of [ 2364554-48-1 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2364554-48-1 ]

* 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 [ 2364554-48-1 ]

[ 2364554-48-1 ] Synthesis Path-Downstream   1~23

  • 1
  • [ 903555-99-7 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 50 °C 2.1: 1,4-dioxane / 8 h / 105 °C 3.1: trifluoroacetic acid / dichloromethane / 20 °C 4.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h 4.2: 3 h
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 50 °C / Inert atmosphere 2: pyridine / 1,4-dioxane / 8 h / 105 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
Multi-step reaction with 4 steps 1.1: hydrogenchloride / dichloromethane; 1,4-dioxane 2.1: phosgene; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 30 - 35 °C / Large scale 2.2: 17.8 h / 20 - 30 °C / Large scale 3.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 3.2: 20 - 65 °C / Large scale 4.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 4.2: 16.6 h / 50 °C / Large scale
  • 2
  • [ 2364560-04-1 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 1,4-dioxane / 8 h / 105 °C 2.1: trifluoroacetic acid / dichloromethane / 20 °C 3.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h 3.2: 3 h
Multi-step reaction with 3 steps 1: 1,4-dioxane / 8 h / 105 °C 2: trifluoroacetic acid / dichloromethane / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 3 h
  • 3
  • [ 2364560-34-7 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / dichloromethane / 20 °C 2.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h 2.2: 3 h
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
  • 4
  • [ 5952-92-1 ]
  • [ 2364560-36-9 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 1-methyl-1H-pyrazole-5-carboxylic acid With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.25h; Stage #2: (1R)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-amine In N,N-dimethyl-formamide for 3h; 15.3 Synthesis of Compound 184: To a solution of 1-methyl-1H-pyrazole-4-carboxylic acid (6.1 g, 48.4 mmol, 1.0 equiv) in DMF (300 mL) were added DIEA (12.6 g, 97.5 mmol, 2.0 equiv), HOAt (19.8 g, 145.8 mmol, 3.0 equiv), and EDCI (28 g, 146.1 mmol, 3.0 equiv). The mixture was stirred for 15 min, and (1R)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-amine (11.2 g, 48.9 mmol, 1.0 equiv) was then added. The mixture was then stirred for 3 h, diluted with DCM, washed with NH4Cl solution three times, dried over sodium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (EA/PE, 74/26) to give an intermediate product. The intermediate product was triturated with a mixture of EA and PE (1/10) to afford 14.5 g (88%) of (R)-N-(5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H- inden-1-yl)-1-methyl-1H-pyrazole-4-carboxamide (Compound 184) as a white solid. LRMS (ES) m/z 338 (M+H). 1H-NMR: (DMSO, 300MHz, ppm): 8.41 (1H, d, J = 8.4 Hz), 8.16 (1H, s), 7.91-7.79 (3H, m), 7.34 (1H, d, J = 7.9 Hz), 5.53 (1H, q, J = 8.3 Hz), 3.84 (3H, s), 3.13-2.81 (4H, m), 2.44 (1H, dd, J = 7.9, 4.7 Hz), 1.95 (1H, m), 1.33 (3H, t, J = 7.5 Hz).
88% With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 3h; 1.iii (iii) Synthesis of (R)-N-(5-(5-ethyl-l,2,4-oxadiazol-3-yl)-2,3-dihydro-lH-inden-l-yl)-l- methyl-lH-pyrazole-4-carboxamide: To a solution of 1 -methyl- 17/-pyrazole-4-carboxylic acid (6.1 g, 48.4 mmol, 1.0 equiv) in DMF (300 mL) were added DIEA (12.6 g, 97.5 mmol, 2.0 equiv), HOAt (19.8 g, 145.8 mmol, 3.0 equiv), and EDCI (28 g, 146.1 mmol, 3.0 equiv). The mixture was stirred for 15 min, and (lR)-5-(5-ethyl-l,2,4-oxadiazol-3-yl)-2,3-dihydro-l//-inden-l-amine (11.2 g, 48.9 mmol, 1.0 equiv) was then added. The mixture was then stirred for 3 h, diluted with DCM, washed with NH4CI solution three times, dried over sodium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (EA/PE, 74/26) to give an intermediate product. The intermediate product was triturated with a mixture of EA and PE (1/10) to afford 14.5 g (88%) of (R)-/V-(5-(5-ethyl-l,2,4-oxadiazol-3-yl)-2,3-dihydro-lH- indcn-1 -yl)- 1 -methyl- 1 //-pyrazolc-4-carboxamidc as a white solid. LRMS (ES) m/z 338 (M+H). 1HNMR: (DMSO, 300MHz, ppm): d 8.41 (1H, d, J = 8.4 Hz), 8.16 (1H, s), 7.91- 7.79 (3H, m), 7.34 (1H, d, J = 7.9 Hz), 5.53 (1H, q , J = 8.3 Hz), 3.84 (3H, s), 3.13-2.81 (4H, m), 2.44 (1H, dd, J = 7.9, 4.7 Hz), 1.95 (1H, m), 1.33 (3H, t, J = 7.5 Hz).
  • 5
  • [ 903555-98-6 ]
  • (R)-N-(5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)-1-methyl-1H-pyrazole-4-carboxamide [ No CAS ]
  • 6
  • [ 1443238-61-6 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C 2.1: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium acetate; XPhos / 1,4-dioxane; water / 5 h / 105 °C 3.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 50 °C 4.1: 1,4-dioxane / 8 h / 105 °C 5.1: trifluoroacetic acid / dichloromethane / 20 °C 6.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h 6.2: 3 h
  • 7
  • [ 5952-92-1 ]
  • [ 2364561-75-9 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
89.14% Stage #1: 1-methyl-1H-pyrazole-4-carboxylic acid With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: (1R)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-amine hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; 1.3 Step 3: preparation of polymorphic Form I of (R)-N-(5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2.3-dihydro-1H-inden-l-yl)-1-methyl-1H-pyrazole-4-carboxamide. To a stirred solution of 1- methyl-1H-pyrazole-4-carboxylic acid (27.1 g, 214.55 mmol, 1.05 equiv) and EDCI (58.8 g, 306.50 mmol, 1.5 equiv) in DMF (540 mL) were added HO At (41.7 g, 306.50 mmol, 1.5 equiv) and DIPEA (105.6 g, 817.34 mmol, 4 equiv) at room temperature. The mixture was stirred for 5 min at room temperature and then added (lR)-5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2.3-dihydro-1H-inden-l-amine hydrochloride (54.3 g, 204.34 mmol, 1 equiv). The resulting mixture was stirred for additional 2 h at room temperature. The reaction was poured into water/ice at room temperature. The precipitated solids were collected by filtration and washed with water (1000 mL) three times. The solid was dissolved in DCM (1500 mL). The organic phase was washed with NH4C1(500 mL sat.aq) three times and brine (500 mL) three times, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude product, which was purified by trituration with EtOAc/n-hexane= 1/2(600 mL) to afford Form I of (R)-N-(5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-l-yl)-1- methyl-1H-pyrazole-4-carboxamide (62.0704 g ,89.14%) as an off-white solid. LRMS (ES) m/z 338 [M+H]. NMR: (DMSO, 300MHz, ppm): d 8.41 (1H, d, J=8.4 Hz), 8.16 (1H, s), 7.91-7.79 (3H, m), 7.34 (1H, d, J=7.9 Hz), 5.53 (1H, q, J=8.3 Hz), 3.84 (3H, s), 3.13-2.81 (4H, m), 2.44 (1H, dd, J=7.9, 4.7 Hz), 1.95 (1H, m), 1.33 (3H, t, J=7.5 Hz).
  • 8
  • [ 79583-19-0 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydroxide / N,N-dimethyl-formamide; 2-methyltetrahydrofuran / 0.5 h / 15 - 25 °C 1.2: 15 - 30 °C 2.1: hydroxylamine / 1-methyl-pyrrolidin-2-one; water; Isopropyl acetate / 3 h / 0 - 70 °C 3.1: 1,1'-carbonyldiimidazole / acetonitrile / 15 - 55 °C
  • 9
  • [ 2364598-42-3 ]
  • [ 79-09-4 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
92.8% With 1,1'-carbonyldiimidazole In acetonitrile at 15 - 55℃; 4.3 Step 3: preparation of polymorphic Form IV of (R)-N-(5-(5-ethyl-1,2,4-oxadiazol- 3-yl)-2,3-dihydro-1H-inden-l-yl)-1-methyl-1H-pyrazole-4-carboxamide. A mixture of Propionic acid (4.25 g, 0.057 mol, 1.10 equiv) and l,l'-Carbonyldiimidazole (CDI) (8.87 g, 0.0547 mol, 1.05 equiv) in acetonitrile (105.1 g, 133.7 mL) was stirred at 20 ± 5 °C until no more than 20% unreacted propionic acid remained as determined by 1 H NMR. The activated propionic acid solution was transferred to (R,Z)-N-(5-(N'-hydroxycarbamimidoyl)-2,3- dihydro-1H-inden-l-yl)-1-methyl-1H-pyrazole-4-carboxamide (15.6 g, 0.0521 mol, 1.00 equiv) in acetonitrile (45.0 g, 57.3 mL). The temperature of the reaction mixture was adjusted to 50 ± 5 °C and the mixture was agitated at 50 ± 5 °C until the (R,Z)-N-(5-(N'- hydroxycarbamimido yl)-2, 3-dihydro- 1H-inden- 1-yl)- 1 -methyl- 1H-pyrazole-4-carboxamide remaining was 70 °C. The mixture was adjusted to 80 ± 5 °C and the resulting slurry was agitated at 80 ± 5 °C for at least 2 hours. The mixture was slowly cooled to 20 ± 5 °C over a period of at least 4 hours and agitated at 20 ± 5 °C for at least 2 hours. The mixture was filtered. The resultant filter cake was washed with water (3 x 120 mL) and dried in a vacuum oven until LOD < 1% is achieved. Material was then packaged. A total of 16.32 g of polymorphic Form IV of (R)-N-(5-(5-ethyl-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H- inden-l-yl)-1-methyl-1H-pyrazole-4-carboxamide was obtained as off-white solid in a yield of 92.8%.
  • 10
  • [ 5952-92-1 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; 2-methyltetrahydrofuran / 0.75 h / 15 - 35 °C 2.1: sodium hydroxide / N,N-dimethyl-formamide; 2-methyltetrahydrofuran / 0.5 h / 15 - 25 °C 2.2: 15 - 30 °C 3.1: hydroxylamine / 1-methyl-pyrrolidin-2-one; water; Isopropyl acetate / 3 h / 0 - 70 °C 4.1: 1,1'-carbonyldiimidazole / acetonitrile / 15 - 55 °C
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
  • 12
  • [ 2364560-04-1 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / 1,4-dioxane / 8 h / 105 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
  • 13
  • [ 903556-00-3 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: phosgene; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 30 - 35 °C / Large scale 1.2: 17.8 h / 20 - 30 °C / Large scale 2.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 2.2: 20 - 65 °C / Large scale 3.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 3.2: 16.6 h / 50 °C / Large scale
  • 14
  • [ 2364561-64-6 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 1.2: 20 - 65 °C / Large scale 2.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 2.2: 16.6 h / 50 °C / Large scale
  • 15
  • [ 2364598-42-3 ]
  • [ 79-09-4 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
97.3 % Stage #1: propionic acid With 1,1'-carbonyldiimidazole In acetonitrile at 20 - 25℃; Large scale; Stage #2: (R)-N-(5-(N'-hydroxycarbamimidoyl)-2,3-dihydro-1H-inden-1-yl)-1-methyl-1H-pyrazole-4-carboxamide With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; Large scale; Further stages; 12 A reactor (vessel 1) was charged with CDI (11.9 kg, 73.67 mol, 1.05 equiv.) and CH3CN (131.4 kg, 167.2 L) and the resulting mixture was treated with propionic acid (5.7 kg, 77.18 mol, 1.10 equiv.) maintaining a temperature of <25 °C. The transfer line was rinsed with CH3CN (10.2 kg, 13.0 L) and the rinse was transferred the bulk reaction mixture. The resulting clear solution was stirred at 20+5 °C for at least 1 h. The reaction was considered to be complete when the IPC was met (specification: free propionic acid < 20 mol% by 1 H NMR; result: 4.8% free propionic acid). A separate reactor (vessel 2) was charged with (R)-N-(5-(N'-hydroxycarbamimidoyl)- 2,3-dihydro-lH-inden-l-yl)-l-methyl-lH-pyrazole-4-carboxamide (21.0 kg, 70.16 mol, 1.00 equiv.) and CH3CN (40.4 kg, 51.4 L). The freshly prepared active imidazole solution in vessel 1 was transferred to vessel 2. Vessel 1 was rinsed with CH3CN (20.2 kg, 25.7 L) and the rinse was transferred to added to vessel 2. The mixture was heated to 50+5 °C. The reaction was stirred at this temperature for at least 12 hours (actual reaction time: 16.6 hours). The mixture was a slurry that as easily stirred. An IPC sample was taken (specification: (R)-N-(5-(N'- hydroxycarbamimidoyl)-2,3-dihydro- IH-inden- 1-yl)- 1 -methyl- lH-pyrazole-4-carboxamide < 2%, result: 0.28%). The reaction was then charged with DBU (21.4 kg, 140.32 mol, 2.00 equiv.). The transfer line was rinsed with CH3CN (6.5 kg, 8.3 L) and the rinse was transferred to the bulk solution. The temperature was adjusted to 70 ± 5 °C and the mixture as stirred at 70 ± 5 °C for at least 2 h until the IPC was met (specification: imidazole intermediate < 2 area%; result: 0.16% imidazole intermediate). The reaction mixture was quenched with the addition of water (64.6 kg) while maintaining the temperature > 50 °C. The temperature was adjusted to 55 ± 5 °C and polish filtered. The solution was concentrated at a temperature of < 50 °C but not below 10 °C until the batch volume was ~ 200 L. The thick slurry was heated to 75 ± 5 °C and the clear solution was diluted with water (417.3 kg) while maintaining the temperature > 70 °C. The temperature was adjusted to 75 ± 5 °C and the mixture was stirred at 75 ± 5 °C for 2 h. Then the mixture was then slowly cooled to 20 ± 5 °C over a period of at least 4 h. The mixture was stirred 20 ± 5 °C for at least 2 h (actual reaction time: 11.5 h). The solid was collected by filtration and the wet cake was washed with water (3 x 161.5 kg). The solid was dried in a vacuum oven at < 50 °C with a slow nitrogen bleed for at least 24 h (actual drying time: 48 h) and analyzed for LOD (specification: LOD < 1% w/w; result: LOD 0.05% w/w). The dried (R)-N-(5-(5-ethyl-l,2,4-oxadiazol-3-yl)-2,3-dihydro-lH-inden-l-yl)-l- methyl-lH-pyrazole-4-carboxamide was analyzed for purity (specification: >97% area; result: 100% area ). A total of 22.0 kg of (R)-N-(5-(5-ethyl-l,2,4-oxadiazol-3-yl)-2,3-dihydro-lH- inden-l-yl)-l-methyl-lH-pyrazole-4-carboxamide (92.8% yield) was obtained. The product (22.0 kg) was then de-lumped to give 21.4 kg (97.3%).
  • 16
  • [ 42348-86-7 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: XPhos; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide; 2-methyltetrahydrofuran / 85 - 95 °C / Large scale 2.1: titanium(IV) tetraethanolate / toluene / 3 h / 75 - 85 °C / Large scale 2.2: 75 - 85 °C / Large scale 3.1: sodium tetrahydroborate / toluene; tetrahydrofuran / -15 - -5 °C / Large scale 4.1: hydrogenchloride / Isopropyl acetate; water / Large scale 5.1: phosgene; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 30 - 35 °C / Large scale 5.2: 17.8 h / 20 - 30 °C / Large scale 6.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 6.2: 20 - 65 °C / Large scale 7.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 7.2: 16.6 h / 50 °C / Large scale
  • 17
  • [ 25724-79-2 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: titanium(IV) tetraethanolate / toluene / 3 h / 75 - 85 °C / Large scale 1.2: 75 - 85 °C / Large scale 2.1: sodium tetrahydroborate / toluene; tetrahydrofuran / -15 - -5 °C / Large scale 3.1: hydrogenchloride / Isopropyl acetate; water / Large scale 4.1: phosgene; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 30 - 35 °C / Large scale 4.2: 17.8 h / 20 - 30 °C / Large scale 5.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 5.2: 20 - 65 °C / Large scale 6.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 6.2: 16.6 h / 50 °C / Large scale
  • 18
  • [ CAS Unavailable ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate / toluene; tetrahydrofuran / -15 - -5 °C / Large scale 2.1: hydrogenchloride / Isopropyl acetate; water / Large scale 3.1: phosgene; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 30 - 35 °C / Large scale 3.2: 17.8 h / 20 - 30 °C / Large scale 4.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 4.2: 20 - 65 °C / Large scale 5.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 5.2: 16.6 h / 50 °C / Large scale
  • 19
  • [ 2901883-99-4 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogenchloride / Isopropyl acetate; water / Large scale 2.1: phosgene; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 30 - 35 °C / Large scale 2.2: 17.8 h / 20 - 30 °C / Large scale 3.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 3.2: 20 - 65 °C / Large scale 4.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 4.2: 16.6 h / 50 °C / Large scale
  • 20
  • [ 1270284-15-5 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 4 h / 0 - 15 °C 2.1: tin(II) chloride dihdyrate / methanol / 20 °C 3.1: triethylamine / dichloromethane / 2.75 h / -5 - 20 °C 4.1: XPhos; XPhos Pd G2; potassium acetate / water; 1,4-dioxane / 5 h / 105 °C / Inert atmosphere 5.1: hydrogenchloride / dichloromethane; 1,4-dioxane 6.1: phosgene; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 30 - 35 °C / Large scale 6.2: 17.8 h / 20 - 30 °C / Large scale 7.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 7.2: 20 - 65 °C / Large scale 8.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 8.2: 16.6 h / 50 °C / Large scale
  • 21
  • [ 34598-49-7 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / toluene; tetrahydrofuran / 4 h / -10 °C / Inert atmosphere 2.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 4 h / 0 - 15 °C 3.1: tin(II) chloride dihdyrate / methanol / 20 °C 4.1: triethylamine / dichloromethane / 2.75 h / -5 - 20 °C 5.1: XPhos; XPhos Pd G2; potassium acetate / water; 1,4-dioxane / 5 h / 105 °C / Inert atmosphere 6.1: hydrogenchloride / dichloromethane; 1,4-dioxane 7.1: phosgene; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 30 - 35 °C / Large scale 7.2: 17.8 h / 20 - 30 °C / Large scale 8.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 8.2: 20 - 65 °C / Large scale 9.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 9.2: 16.6 h / 50 °C / Large scale
  • 22
  • [ 1334784-73-4 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: tin(II) chloride dihdyrate / methanol / 20 °C 2.1: triethylamine / dichloromethane / 2.75 h / -5 - 20 °C 3.1: XPhos; XPhos Pd G2; potassium acetate / water; 1,4-dioxane / 5 h / 105 °C / Inert atmosphere 4.1: hydrogenchloride / dichloromethane; 1,4-dioxane 5.1: phosgene; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 30 - 35 °C / Large scale 5.2: 17.8 h / 20 - 30 °C / Large scale 6.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 6.2: 20 - 65 °C / Large scale 7.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 7.2: 16.6 h / 50 °C / Large scale
  • 23
  • [ 1228561-27-0 ]
  • [ 2364554-48-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: triethylamine / dichloromethane / 2.75 h / -5 - 20 °C 2.1: XPhos; XPhos Pd G2; potassium acetate / water; 1,4-dioxane / 5 h / 105 °C / Inert atmosphere 3.1: hydrogenchloride / dichloromethane; 1,4-dioxane 4.1: phosgene; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 30 - 35 °C / Large scale 4.2: 17.8 h / 20 - 30 °C / Large scale 5.1: hydroxylamine / water; 1-methyl-pyrrolidin-2-one / 5 - 20 °C / Large scale 5.2: 20 - 65 °C / Large scale 6.1: 1,1'-carbonyldiimidazole / acetonitrile / 20 - 25 °C / Large scale 6.2: 16.6 h / 50 °C / Large scale
Same Skeleton Products
Historical Records