Home Cart 0 Sign in  

[ CAS No. 1613191-99-3 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1613191-99-3
Chemical Structure| 1613191-99-3
Structure of 1613191-99-3 * Storage: {[proInfo.prStorage]}

Quality Control of [ 1613191-99-3 ]

Related Doc. of [ 1613191-99-3 ]

SDS
Alternatived Products of [ 1613191-99-3 ]
Alternatived Products of [ 1613191-99-3 ]

Product Details of [ 1613191-99-3 ]

CAS No. :1613191-99-3 MDL No. :MFCD31803930
Formula : C25H29F2N9O3 Boiling Point : -
Linear Structure Formula :- InChI Key :NC1=NN2C=C(F)C=NC2=C1C(=O)NC1=C(N2CCC(CC2)C(=O)N2CCN(CC2)C2COC2)C(F)=CN=C1
M.W :541.55 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1613191-99-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1613191-99-3 ]

  • Downstream synthetic route of [ 1613191-99-3 ]

[ 1613191-99-3 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 1254115-22-4 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium(II) hydroxide; hydrogen / methanol; ethyl acetate 2: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 2 steps 1.1: hydrogen; palladium(II) hydroxide / ethyl acetate; methanol / 20 h 2.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 0.5 h / 20 °C 2.2: 0.5 h / 20 °C
Multi-step reaction with 2 steps 1: hydrogen; palladium(II) hydroxide / ethyl acetate; methanol / 20 h 2: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
  • 2
  • [ 1613191-76-6 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium 4-methylbenzenesulfinate; tetrakis(triphenylphosphine) palladium(0) / dimethyl sulfoxide / 2 - 3 h / 25 - 30 °C / Inert atmosphere 2: triethylamine / acetonitrile / 2 h / 20 °C 3: pyridine / 95 °C / Inert atmosphere 4: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 5: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 6 steps 1: sodium 4-methylbenzenesulfinate; tetrakis(triphenylphosphine) palladium(0) / dimethyl sulfoxide / 2 - 3 h / 25 - 30 °C / Inert atmosphere 2: triethylamine / acetonitrile / 2 h / 20 °C 3: pyridine / 95 °C / Inert atmosphere 4: triethylsilane / dichloromethane / 20 - 40 °C 5: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 6: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 5 steps 1: phenylsilane; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 2.5 h / 20 °C 2: triethylamine / acetonitrile / 2 h / 20 °C 3: pyridine / 95 °C / Inert atmosphere 4: acetonitrile / 16 h / 75 - 80 °C 5: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 5 steps 1: phenylsilane; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 2.5 h / 20 °C 2: triethylamine; thionyl chloride / dichloromethane / 20 - 40 °C 3: pyridine / 16 h / 90 - 100 °C 4: acetonitrile / 16 h / 75 - 80 °C 5: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere

  • 3
  • [ 1613191-77-7 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / acetonitrile / 2 h / 20 °C 2: pyridine / 95 °C / Inert atmosphere 3: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 4: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 5 steps 1: triethylamine / acetonitrile / 2 h / 20 °C 2: pyridine / 95 °C / Inert atmosphere 3: triethylsilane / dichloromethane / 20 - 40 °C 4: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 5: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 4 steps 1: triethylamine / acetonitrile / 2 h / 20 °C 2: pyridine / 95 °C / Inert atmosphere 3: acetonitrile / 16 h / 75 - 80 °C 4: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 4 steps 1: triethylamine; thionyl chloride / dichloromethane / 20 - 40 °C 2: pyridine / 16 h / 90 - 100 °C 3: acetonitrile / 16 h / 75 - 80 °C 4: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere

  • 4
  • [ 1613191-78-8 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / 95 °C / Inert atmosphere 2: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 3: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 4 steps 1: pyridine / 95 °C / Inert atmosphere 2: triethylsilane / dichloromethane / 20 - 40 °C 3: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 4: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 3 steps 1: pyridine / 95 °C / Inert atmosphere 2: acetonitrile / 16 h / 75 - 80 °C 3: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
  • 5
  • [ 1613192-01-0 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / 95 °C / Inert atmosphere 2: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 3: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 4 steps 1: pyridine / 95 °C / Inert atmosphere 2: triethylsilane / dichloromethane / 20 - 40 °C 3: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 4: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 3 steps 1: pyridine / 16 h / 90 - 100 °C 2: acetonitrile / 16 h / 75 - 80 °C 3: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 3 steps 1: pyridine / 95 °C / Inert atmosphere 2: acetonitrile / 16 h / 75 - 80 °C 3: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere

  • 6
  • [ 1613192-00-9 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 2: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 3 steps 1: triethylsilane / dichloromethane / 20 - 40 °C 2: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 3: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 2 steps 1: acetonitrile / 16 h / 75 - 80 °C 2: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
  • 7
  • [ 1254115-23-5 ]
  • [ 1613192-04-3 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
86% With N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran Inert atmosphere; 3f.4; 3f.3 Step 4: 2-amino-6-fluoro-N-[5-fluoro-4-[4-[4-(oxetan-3-yl)piperazine-1-carbonyl]-1- piperidyl]-3-pyridyI]pyrazolo[1,5-a]pyrimidine-3-carboxamide (Compound I-G-32) To a yellow suspension of l-[3-[(2-amino-6-fluoro-pyrazolo[l,5-a]pyrimidine-3- carbonyl)amino]-5-fluoro-4-pyridyl]piperidine-4-carboxylic acid (Hydrochloric Acid) 30 (59.7 g, 131.5 mmol) in NMP (477.6 mL) was added DIPEA (50.99 g, 68.72 mL, 394.5 mmol) then [(6-chlorobenzotriazol- 1 -yl)oxy-(dimethylamino)methylene] -dimethyl- ammonium (Boron Tetrafluoride Ion (1)) (51.44 g, 144.7 mmol). A yellow suspension forms after a few minutes. The mixture was sirred for 30 mins at room temperature then l-(oxetan- 3-yl)piperazine 25 (prepared according to Preparation N-32, below) (26.18 g, 184.1 mmol) was added. The cream/tan suspension turns to an orange solution (exotherms from 23.9 to 29.4°C). The flask was placed on ice/water bath until internal temperature was at 24°C, then ice bath was removed and internal temperature steady at 24°C thereafter. [00330] The solution was stirred for 30 mins at room temperature then cooled on an ice/salt/water bath to 10°C before the slow addition of water (1.015 L) in 100 mL portions. Prior to adding the next lOOmL of water, waited for exotherm to between 17°C and 20°C (internal) then allow to cool to between 10 and 15°C. Repeated until all water added. Once exotherm had ceased, ice/salt/water bath removed and mixture stirred at ambient temperature for 20 mins (thick yellow/cream suspension forms). Solid collected by filtration through a sinter funnel, washed well with water then dried by suction for 10 mins. Vacuum removed and solid slurried in water on sinter funnel, then vacuum reapplied and solid dried by suction overnight then dried in vacuum oven for 24 h at 40°C <10 mBar. [00331] Solid (54.5g) suspended in ethanol (545 mL, 10 vol eq.) and heated under reflux for 2h then cooled to room temperature over 2h. Solid collected by filtration, washed with minimum ethanol and dried by suction for lh to leave product as a pale yellow solid. Solid placed in vacuum oven at 23.5°C and <10mBar overnight to leave product I-G-32 as a pale yellow solid, (51g, 64% yield). 'H NMR (500 MHz, DMSO-d6) δ 10.64 (s, 1H), 9.67 (s, 1H), 9.48 (dd, 1H), 9.26 (dd, 1H), 8.26 (d, 1H), 6.79 (s, 2H), 4.55 (t, 2H), 4.47 (t, 2H), 4.34 (t, 0.7H), 3.61 (dt, 4H), 3.48 - 3.41 (m, 2.5H), 3.22 - 3.17 (m, 2H), 3.05 - 3.03 (m, 2H), 3.99 - 2.93 (m, 1H), 2.28 (dt, 4H), 2.17 - 2.10 (m, 2H), 1.74 (d, 2H), 1.07 (t, 2H). MS (ES+) 542.3.; To a solution of l-(oxetan-3-yl)piperazine (525mg, 3.69mmol) in THF (12ml) was added DIPEA (1.72ml, 9.91mmol), followed by l-(3-(2-amino-6-fluoropyrazolo[l,5- a]pyrimidine-3 -carboxamido)-5 -fluoropyridin-4-yl)piperidine-4-carboxylic acid(hydrochloride salt, 1.5g, 3.3mmol). [(6-chlorobenzotriazol-l-yl)oxy- (dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate (TCTU, 1.29g,3.64mmol) was added and the mixture stirred under nitrogen until reaction completion (determined by HPLC analysis). The mixture was cooled and water (24ml) was added dropwise. The mixture was allowed to warm to ambient and stirred for 3 hrs, then filtered. The filter cake was washed with (3x3 ml). The damp cake was dried under vacuum (with a nitrogen bleed) at 40°C. The product was obtained as a yellow solid (1.54g, 86%); XH NMR (500 MHz, DMSO-d6) δ 10.64 (s, 1H), 9.67 (s, 1H), 9.48 (dd, 1H), 9.26 (dd, 1H), 8.26 (d, 1H), 6.79 (s, 2H), 4.55 (t, 2H), 4.47 (t, 2H), 4.34 (t, 0.7H), 3.61 (dt, 4H), 3.48 - 3.41 (m, 2.5H), 3.22 - 3.17 (m, 2H), 3.05 - 3.03 (m, 2H), 3.99 - 2.93 (m, 1H), 2.28 (dt, 4H), 2.17 - 2.10 (m, 2H), 1.74 (d, 2H), 1.07 (t, 2H); 19F NMR (500 MHz, DMSO-d6) δ - 152.8, -136.1 ; MS (ES+) 542.3.
64% Stage #1: 1-[3-[(2-amino-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]-5-fluoro-4-pyridyl]piperidine-4-carboxylic acid hydrochloride With N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h; Stage #2: 1-(oxetan-3-yl)-piperazine In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h; 1.4; 2.3 Step 4: 2-amino-6-fluoro-N-[5-fluoro-4-[ 4-[ 4-( oxetan-3-yl)piperazine-1-carbonyl]-1-piperidy 1]-3 -pyridyl]pyrazolo [ 1,5-a]pyrimidine-3-carboxamide (Compound I-1) [0475] To a yellow suspension of 1-[3-[(2-amino-6-fluoropyrazolo[1 ,5-a ]pyrimidine-3-carbonyl)amino ]-5-fluoro-4-pyridyl]piperidine-4-carboxylic acid (Hydrochloric Acid) 30(59.7 g, 131.5 mmol) in NMP (477.6 mL) was added DIPEA(50.99 g, 68.72 mL, 394.5 mmol) then [(6-chlorobenzotriazol-1-y l)oxy -( dimethylamino )methylene ]-dimethy -ammonium(Boron Tetrafluoride Ion (1)) (51.44 g, 144.7 mmol). Ayellow suspension forms after a few minutes. The mixturewas stirred for 30 mins at room temperature then 1-(oxetan-3-yl)piperazine 25 (prepared according to Preparation 8,below) (26.18 g, 184.1 mmol) was added. The cream/tansuspension turns to an orange solution (exotherms from 23.9to 29.4° C.). The flask was placed on ice/water bath untilinternal temperature was at 24 o C., then ice bath was removedand internal temperature steady at 24 o C. thereafter.then cooled on an ice/salt/water bath to 1 oo C. beforethe slow addition of water (1.015 L) in 100 mL portions. Priorto adding the next 100 mL of water, waited for exotherm tobetween 17° C. and 20° C. (internal) then allow to cool tobetween 10 and 15° C. Repeated until all water added. Onceexotherm had ceased, ice/salt/water bath removed and mixturestirred at ambient temperature for 20 mins (thick yellow/cream suspension forms). Solid collected by filtrationthrough a sinter funnel, washed well with water then dried bysuction for 10 mins. Vacuum removed and solid slurried inwater on sinter funnel, then vacuum reapplied and solid driedby suction overnight then dried in vacuum oven for 24 hat 40°C.
  • 8
  • [ 407-20-5 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.17 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium carbonate / cyclohexanol / 18 h / 120 °C / Inert atmosphere 3.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 3.2: 0.5 h / 20 °C 4.1: pyridine / 95 °C / Inert atmosphere 5.1: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 6.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 6 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.17 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide / dichloromethane / 1 h / Cooling with ice 2.2: 2 h / 130 °C 2.3: 20 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 3.2: 0.5 h / 20 °C 4.1: pyridine / 95 °C / Inert atmosphere 5.1: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 6.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.17 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide / dichloromethane / 1 h / Cooling with ice 2.2: 2 h / 130 °C 2.3: 20 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 3.2: 0.5 h / 20 °C 4.1: pyridine / 95 °C / Inert atmosphere 5.1: triethylsilane / dichloromethane / 20 - 40 °C 6.1: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 7.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -70 °C 1.2: -78 - 20 °C 2.1: hydrogenchloride / pentane; diethyl ether / 0.08 h 3.1: sodium carbonate / cyclohexanol / 18 h / 120 °C / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 4.2: 0.5 h / 20 °C 5.1: pyridine / 95 °C / Inert atmosphere 6.1: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 7.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -70 °C 1.2: -78 - 20 °C 2.1: hydrogenchloride / pentane; diethyl ether / 0.08 h 3.1: sodium hydroxide / dichloromethane / 1 h / Cooling with ice 3.2: 2 h / 130 °C 3.3: 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 4.2: 0.5 h / 20 °C 5.1: pyridine / 95 °C / Inert atmosphere 6.1: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 7.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.17 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium carbonate / cyclohexanol / 18 h / 120 °C / Inert atmosphere 3.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 3.2: 0.5 h / 20 °C 4.1: pyridine / 95 °C / Inert atmosphere 5.1: triethylsilane / dichloromethane / 20 - 40 °C 6.1: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 7.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 8 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -70 °C 1.2: -78 - 20 °C 2.1: hydrogenchloride / pentane; diethyl ether / 0.08 h 3.1: sodium hydroxide / dichloromethane / 1 h / Cooling with ice 3.2: 2 h / 130 °C 3.3: 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 4.2: 0.5 h / 20 °C 5.1: pyridine / 95 °C / Inert atmosphere 6.1: triethylsilane / dichloromethane / 20 - 40 °C 7.1: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 8.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 8 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -70 °C 1.2: -78 - 20 °C 2.1: hydrogenchloride / pentane; diethyl ether / 0.08 h 3.1: sodium carbonate / cyclohexanol / 18 h / 120 °C / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 4.2: 0.5 h / 20 °C 5.1: pyridine / 95 °C / Inert atmosphere 6.1: triethylsilane / dichloromethane / 20 - 40 °C 7.1: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 8.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.17 h / -78 °C 1.2: -78 - 20 °C 1.3: 0.33 h 2.1: sodium carbonate / cyclohexanol / 40 - 120 °C / Inert atmosphere 3.1: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 4.1: pyridine / 16 h / 90 - 100 °C 5.1: acetonitrile / 16 h / 75 - 80 °C 6.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 6 steps 1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.17 h / -78 °C 1.2: -78 - 20 °C 1.3: 0.33 h 2.1: sodium carbonate / cyclohexanol / 40 - 120 °C / Inert atmosphere 3.1: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 4.1: pyridine / 95 °C / Inert atmosphere 5.1: acetonitrile / 16 h / 75 - 80 °C 6.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 8 steps 1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.17 h / -78 °C 1.2: -78 - 20 °C 1.3: 0.33 h 2.1: sodium hydroxide / dichloromethane / 1 h / Cooling with ice 3.1: potassium fluoride; tetramethlyammonium chloride / dimethyl sulfoxide / 2 h / Heating 4.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 20 °C 5.1: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 6.1: pyridine / 16 h / 90 - 100 °C 7.1: acetonitrile / 16 h / 75 - 80 °C 8.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 8 steps 1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.17 h / -78 °C 1.2: -78 - 20 °C 1.3: 0.33 h 2.1: sodium hydroxide / dichloromethane / 1 h / Cooling with ice 3.1: potassium fluoride; tetramethlyammonium chloride / dimethyl sulfoxide / 2 h / Heating 4.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 20 °C 5.1: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 6.1: pyridine / 95 °C / Inert atmosphere 7.1: acetonitrile / 16 h / 75 - 80 °C 8.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere

  • 10
  • [ 1613192-96-3 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydroxide / dichloromethane / 1 h / Cooling with ice 1.2: 2 h / 130 °C 1.3: 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 2.2: 0.5 h / 20 °C 3.1: pyridine / 95 °C / Inert atmosphere 4.1: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 5.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 5 steps 1.1: sodium carbonate / cyclohexanol / 18 h / 120 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 2.2: 0.5 h / 20 °C 3.1: pyridine / 95 °C / Inert atmosphere 4.1: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 5.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 6 steps 1.1: sodium hydroxide / dichloromethane / 1 h / Cooling with ice 1.2: 2 h / 130 °C 1.3: 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 2.2: 0.5 h / 20 °C 3.1: pyridine / 95 °C / Inert atmosphere 4.1: triethylsilane / dichloromethane / 20 - 40 °C 5.1: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 6.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 6 steps 1.1: sodium carbonate / cyclohexanol / 18 h / 120 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 2.2: 0.5 h / 20 °C 3.1: pyridine / 95 °C / Inert atmosphere 4.1: triethylsilane / dichloromethane / 20 - 40 °C 5.1: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 6.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 5 steps 1: sodium carbonate / cyclohexanol / 40 - 120 °C / Inert atmosphere 2: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 3: pyridine / 16 h / 90 - 100 °C 4: acetonitrile / 16 h / 75 - 80 °C 5: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 5 steps 1: sodium carbonate / cyclohexanol / 40 - 120 °C / Inert atmosphere 2: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 3: pyridine / 95 °C / Inert atmosphere 4: acetonitrile / 16 h / 75 - 80 °C 5: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1: sodium hydroxide / dichloromethane / 1 h / Cooling with ice 2: potassium fluoride; tetramethlyammonium chloride / dimethyl sulfoxide / 2 h / Heating 3: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 20 °C 4: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 5: pyridine / 16 h / 90 - 100 °C 6: acetonitrile / 16 h / 75 - 80 °C 7: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1: sodium hydroxide / dichloromethane / 1 h / Cooling with ice 2: potassium fluoride; tetramethlyammonium chloride / dimethyl sulfoxide / 2 h / Heating 3: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 20 °C 4: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 5: pyridine / 95 °C / Inert atmosphere 6: acetonitrile / 16 h / 75 - 80 °C 7: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere

  • 11
  • [ 1613193-36-4 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 1.2: 0.5 h / 20 °C 2.1: pyridine / 95 °C / Inert atmosphere 3.1: hydrogenchloride / water; 1,4-dioxane / Inert atmosphere 4.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 5 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; Benzophenone imine; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere 1.2: 0.5 h / 20 °C 2.1: pyridine / 95 °C / Inert atmosphere 3.1: triethylsilane / dichloromethane / 20 - 40 °C 4.1: hydrogenchloride / 1-methyl-pyrrolidin-2-one; 1,4-dioxane / 0.33 h / 20 °C 5.1: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 4 steps 1: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 2: pyridine / 16 h / 90 - 100 °C 3: acetonitrile / 16 h / 75 - 80 °C 4: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 4 steps 1: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 2: pyridine / 95 °C / Inert atmosphere 3: acetonitrile / 16 h / 75 - 80 °C 4: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere

  • 12
  • [ 138007-24-6 ]
  • [ 1613191-99-3 ]
  • 13
  • [ 882738-24-1 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C 2: sodium carbonate / cyclohexanol / 40 - 120 °C / Inert atmosphere 3: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 4: pyridine / 16 h / 90 - 100 °C 5: acetonitrile / 16 h / 75 - 80 °C 6: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 6 steps 1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C 2: sodium carbonate / cyclohexanol / 40 - 120 °C / Inert atmosphere 3: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 4: pyridine / 95 °C / Inert atmosphere 5: acetonitrile / 16 h / 75 - 80 °C 6: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
  • 14
  • [ 1254115-23-5 ]
  • 1-[3-[(2-amino-6-fluoropyrazolo[1,5-a]pyrimidine-3-carbonyl)amino]-5-fluoro-4-pyridyl]piperidine-4-carboxylic acid mesylate [ No CAS ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
59% With N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran Inert atmosphere; 3.3 Step 3: 2-amino-6-fluoro-N-[5-fluoro-4-[ 4-[ 4-( oxetan-3-yl)piperazine-1-carbonyl]-1-piperidy 1]-3 -pyridyl]pyrazolo [ 1,5-a]pyrimidine-3-carboxamide (Compound I-1 Amorphous) [0492] N,N-Diisopropylethylamine (51 uL; 38 mg; 0.29mmol) was added to a suspension of 1-[3-[(2-amino-6-fluoro-pyrazolo[ 1 ,5-a ]pyrimidine-3-carbonyl)amino ]-5-fluoro-4-pyridyl]piperidine-4-carboxylic acid mesylate (50mg; 0.097 mmol) and 1-( oxetan-3-yl)piperazine (15 mg; 0.11mmol) in THF (1.00 mL). [(6-chlorobenzotriazol-1-yl)oxy(dimethy amino )methylene ]-dimethyl-ammonium tetrafluoroborate(TCTU, 36.3 mg; 0.10 mmol) was added and themixture stirred under nitrogen until reaction completion (determinedby HPLC analysis). Water (2 mL) was added to thesuspension and stirred for 5 hours. The solids were collectedby filtration, washed with water (2x200 uL ), dried by suctionthen dried in a vacuum oven for 24 hours at 45-50° C. to giveI-1 as a pale yellow solid (31 mg; 59%).
  • 15
  • [ 10314-98-4 ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / -3.4 - 20 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C 3: sodium carbonate / cyclohexanol / 40 - 120 °C / Inert atmosphere 4: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 5: pyridine / 16 h / 90 - 100 °C 6: acetonitrile / 16 h / 75 - 80 °C 7: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / -3.4 - 20 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C 3: sodium carbonate / cyclohexanol / 40 - 120 °C / Inert atmosphere 4: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 5: pyridine / 95 °C / Inert atmosphere 6: acetonitrile / 16 h / 75 - 80 °C 7: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
  • 16
  • C5H2BrF2N [ No CAS ]
  • [ 1613191-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 20 °C 2: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 3: pyridine / 16 h / 90 - 100 °C 4: acetonitrile / 16 h / 75 - 80 °C 5: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 20 °C 2: Benzophenone imine; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 95 °C / Inert atmosphere 3: pyridine / 95 °C / Inert atmosphere 4: acetonitrile / 16 h / 75 - 80 °C 5: N-[(6-chlorobenzotriazol-1-yl)oxy-(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / Inert atmosphere
Historical Records