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CAS No. : | 1357600-61-3 | MDL No. : | MFCD27991442 |
Formula : | C12H24N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MNJCZOJFFXXZKR-SECBINFHSA-N |
M.W : | 228.33 | Pubchem ID : | 68945318 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / -78 - -20 °C 2: palladium on activated charcoal; hydrogen / methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 20h; | C Step C: Compound VI - tert-Butyl (R)-4-amino-3,3-dimethylpiperidine-1- carboxylate To a degassed solution of tert-butyl (R)-3,3-dimethyl-4-(((R)-1-phenylethyl)amino)- piperidine-1-carboxylate XXII (44.9 g, 135 mmol) in ethanol (1150 mL) 10% Pd/C (4.0 g) was added. Reaction mixture was stirred at room temperature under hydrogen atmosphere for 20 hours. The mixture was filtered through bed of Celite and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent: AcOEt to AcOEt: methanol = 50:50, v/v). Product was obtained as a colorless oil (26.5 g, 116 mmol) with the yield of 86%. 1H NMR (300 MHz, CDCl3 ) δ 4.20-3,88 (m, 1H), 3.85-3.53 (m, 1H), 2.95-2.70 (m, 1H), 2.60- 2.45 (m, 1H), 2.50 (dd, J= 10.9, 4.2 Hz, 1H), 1.68-1.54 (m, 1H), 1.45 (s, 9H), 1.45- 1.32 (m, 1H), 1.13 (bs, 2H), 0.93 (s, 3H), 0.82 (s, 3H). |
62% | With palladium on activated charcoal; hydrogen In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide 2: hydrogenchloride / water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: titanium tetrachloride; triethylamine / dichloromethane / 60 °C 2: sodium tetrahydroborate / ethanol / -78 - -20 °C 3: palladium on activated charcoal; hydrogen / methanol | ||
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / 24 h / Reflux; Dean-Stark 2: sodium tetrahydroborate; ethanol / toluene / 3 h / -70 - 20 °C / Dean-Stark 3: palladium 10% on activated carbon; hydrogen / ethanol / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With N-ethyl-N,N-diisopropylamine In ISOPROPYLAMIDE at 90℃; for 3h; | 55.1 Example 55[00292] (R)-4-(l-(2-amino-2-oxoacetyl)-3,3-dimethylpiperidin-4-ylamino)-6-(6- methoxypyridin-3-yl)pyrrolo[l,2-b]pyridazine-3-carboxamide Step 1; (R)-tert-butyl 4-(6-bromo-3-carbamoylpyrrolo[l,2-b]pyridazin-4-ylamino)-3,3- dimethylpiperidine- 1 -carboxylate [00293] 6-bromo-4-chloropyrrolo[l,2-b]pyridazine-3-carboxamide (Intermediate 2, 600mg, 2.186 mmol), (R)-tert-butyl 4-amino-3,3-dimethylpiperidine-l-carboxylate (549 mg, 2.404 mmol) and DIPEA (0.764 mL, 4.37 mmol) in DMA (3.0 mL) was heated at 90 °C for 3 h. The mixture was cooled and added to crushed ice, stirred for 30 min, then extracted with EtOAc (100 mL x 3). The combined organic extracts were washed with brine, filtered and concentrated to afford brown oil, which was added to water and stirred for 2h to afford a solid which was collected by vacuum filtration and dried to afford the title compound as a tan solid (546 mg, 1.17 mmol, 54%). HPLC (Method B) retention time = 3.91 min. LCMS (m+1) = 466/468(1 : 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / ISOPROPYLAMIDE / 3 h / 90 °C 2: potassium phosphate / palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 1 h / 90 °C / Inert atmosphere; Sealed tube 3: dichloromethane / 0.5 h / 20 °C 4: triethylamine; HATU / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / ISOPROPYLAMIDE / 3 h / 90 °C 2: potassium phosphate / palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 1 h / 90 °C / Inert atmosphere; Sealed tube 3: dichloromethane / 0.5 h / 20 °C 4: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / ISOPROPYLAMIDE / 3 h / 90 °C 2: potassium phosphate / palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 1 h / 90 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / ISOPROPYLAMIDE / 3 h / 90 °C 2: potassium phosphate / palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 1 h / 90 °C / Inert atmosphere; Sealed tube 3: dichloromethane / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; ethanol / toluene / 3 h / -70 - 20 °C / Dean-Stark 2: palladium 10% on activated carbon; hydrogen / ethanol / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: triethylamine / acetonitrile / 20.25 h / 20 °C 2: lithium hydroxide; water / ethanol / 1.5 h / 55 °C 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 4: ammonium hydroxide / dichloromethane / 0.5 h / 20 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6: triethylamine / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 20.25 h / 20 °C 2: lithium hydroxide; water / ethanol / 1.5 h / 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / acetonitrile / 20.25 h / 20 °C 2: lithium hydroxide; water / ethanol / 1.5 h / 55 °C 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 4: ammonium hydroxide / dichloromethane / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / acetonitrile / 20.25 h / 20 °C 2: lithium hydroxide; water / ethanol / 1.5 h / 55 °C 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triethylamine / acetonitrile / 20.25 h / 20 °C 2: lithium hydroxide; water / ethanol / 1.5 h / 55 °C 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 4: ammonium hydroxide / dichloromethane / 0.5 h / 20 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: triethylamine / acetonitrile / 20.25 h / 20 °C 2: lithium hydroxide; water / ethanol / 1.5 h / 55 °C 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 4: ammonium hydroxide / dichloromethane / 0.5 h / 20 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6: triethylamine / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 7: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / 1,4-dioxane; water / 3 h / 120 °C / Schlenk technique; Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: triethylamine / acetonitrile / 20.25 h / 20 °C 2: lithium hydroxide; water / ethanol / 1.5 h / 55 °C 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 4: ammonium hydroxide / dichloromethane / 0.5 h / 20 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6: triethylamine / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 7: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / 1,4-dioxane; water / 3 h / 120 °C / Schlenk technique; Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In acetonitrile at 20℃; for 20.25h; | 3 Step 3: Ethyl (R)-2-bromo-7-((1-(tert-butoxycarbonyl)-3,3-dimethylpiperidin-4-yl)- amino)pyrazolo[1,5-a]pyrimidine-6-carboxylate VII Triethylamine (8.05 mL, 57.7 mmol) was added to the acetonitrile (150 mL) solution of ethyl 2-bromo-7-chloropyrazolo[1,5-a]pyridimine-6-carboxylate VI (5.86 g, 19.2 mmol) obtained in Step 2. Subsequently, to the mixture solution of tert-butyl (R)-4- amino-3,3-dimethylpiperidine-1-carboxylate VI (Intermediate P1) (4.61 g, 20.2 mmol) in acetonitrile (30 mL) was added dropwise during 15 minutes. Reaction mixture was stirred at room temperature for 20 hours and then concentrated under reduced pressure. The residue was dissolved in AcOEt (100 mL) and water (100 mL) was added. After separation of phases, aqueous phase was extracted with AcOEt (2 x 100 mL). Organic phases were combined, washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent: heptane:AcOEt = 95:5 to 85: 15, v/v). Product was obtained as a creamy amorphous solid (8.08 g, 16.3 mmol) with the yield 85%. MS-ESI: (m/z) calculated for C21H31BrN5O4[M+H]+= 496.2, found 496.2. 1H NMR (300 MHz, CDCl3 ) δ 9.84 (d, J=8.8 Hz, 1H), 8.70 (s, 1H), 6.47 (s, 1H), 5.32 (t, J=8.6 Hz, 1H), 4.38 (q, 3=1.1 Hz, 2H), 4.20-3.95 (m, 1H), 3.93-3.65 (m, 1H), 3.13-2.93 (m, 1H), 2.90-2.70 (m, 1H), 2.08-1.95 (m, 1H), 1.80-1.65 (m, 1H), 1.48 (s, 9H), 1.41 (t, 3=1 Hz, 3H), 1.09 (s, 3H), 1.00 (s, 3H). |
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