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CAS No.: | 478149-53-0 |
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Name: | N-(3R)-1-Azabicyclo[2.2.2]oct-3-yl-furo[2,3- c]pyridine- 5-carboxamide hydrochloride PHA 543613 hydrochloride |
Molecular Structure: | |
Formula: | C15H17N3O2.2HCl |
Molecular Weight: | 271.319 |
Synonyms: | N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide,hydrochloride; |
Solubility: | Soluble to 100 mM in water and to 100 mM in DMSO |
PSA: | 58.37000 |
LogP: | 2.78260 |
furo[2,3-c]pyridine-5-carboxylic acid
(R)-quinuclidine-3-amine hydrochloride
PHA-543613
Conditions | Yield |
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With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 16h; | 66% |
furo[2,3-c]pyridine-5-carboxylic acid
(3R)-quinuclidin-3-amine dihydrochloride
PHA-543613
Conditions | Yield |
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With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 3h; | |
With N-ethyl-N,N-diisopropylamine; HATU In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 2.5h; |
furo[2,3-c]pyridine-5-carbaldehyde
PHA-543613
Conditions | Yield |
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Multi-step reaction with 2 steps 1: aq. KH2PO4; sodium chlorite / dimethylsulfoxide 2: diisopropylethylamine; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF6 / dimethylformamide / 3 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme |
furo[2,3-c]pyridin-5-yl methanol
PHA-543613
Conditions | Yield |
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Multi-step reaction with 3 steps 1: 86 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 2: aq. KH2PO4; sodium chlorite / dimethylsulfoxide 3: diisopropylethylamine; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF6 / dimethylformamide / 3 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 1.2: 1 h / -78 - 20 °C 2.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme |
2-chloro-3-hydroxypyridine
PHA-543613
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: aq. NaHCO3 / 15 h / 90 °C 2: aq. NaHCO3; I2 / 48 h / 20 °C 3: 11.4 g / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran; CHCl3 / 3 h / 20 °C 4: CuI; diisopropylamine / methanol / 6 h / 45 - 50 °C 5: 19.5 g / Zn; aq. HCl / ethanol / 1 h / Heating 6: 86 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 7: aq. KH2PO4; sodium chlorite / dimethylsulfoxide 8: diisopropylethylamine; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF6 / dimethylformamide / 3 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sodium hydrogencarbonate / water / 26.5 h / 90 °C 2.1: iodine; sodium hydrogencarbonate / water / 20 °C 3.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran; chloroform / 3 h / 20 °C 4.1: triethylamine / copper(l) iodide / ethanol / 3.5 h / 70 °C 5.1: hydrogenchloride; zinc / ethanol; water / 1 h / 70 °C / Heating / reflux 6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 6.2: 1 h / -78 - 20 °C 7.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sodium hydrogencarbonate / water / 26.5 h / 90 °C 2.1: iodine; sodium hydrogencarbonate / water / 20 °C 3.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran; chloroform / 3 h / 20 °C 4.1: diisopropylamine / copper(l) iodide / methanol / 6 h / 45 - 50 °C 5.1: hydrogenchloride; zinc / ethanol; water / 1 h / 70 °C / Heating / reflux 6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 6.2: 1 h / -78 - 20 °C 7.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: sodium hydrogencarbonate / water / 26.5 h / 90 °C 2.1: iodine; sodium hydrogencarbonate / water / 20 °C 3.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran; chloroform / 3 h / 20 °C 4.1: triethylamine / copper(l) iodide / ethanol / 3.5 h / 70 °C 5.1: palladium 10% on activated carbon; cyclohexene / ethanol / 2.5 h / Heating / reflux 6.1: sodium hydroxide / methanol; water / 1.5 h / 20 °C 7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 7.2: 1 h / -78 - 20 °C 8.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 9.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme |
2-chloro-6-(hydroxymethyl)-3-pyridinol
PHA-543613
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: aq. NaHCO3; I2 / 48 h / 20 °C 2: 11.4 g / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran; CHCl3 / 3 h / 20 °C 3: CuI; diisopropylamine / methanol / 6 h / 45 - 50 °C 4: 19.5 g / Zn; aq. HCl / ethanol / 1 h / Heating 5: 86 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 6: aq. KH2PO4; sodium chlorite / dimethylsulfoxide 7: diisopropylethylamine; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF6 / dimethylformamide / 3 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: iodine; sodium hydrogencarbonate / water / 20 °C 2.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran; chloroform / 3 h / 20 °C 3.1: triethylamine / copper(l) iodide / ethanol / 3.5 h / 70 °C 4.1: hydrogenchloride; zinc / ethanol; water / 1 h / 70 °C / Heating / reflux 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 5.2: 1 h / -78 - 20 °C 6.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: iodine; sodium hydrogencarbonate / water / 20 °C 2.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran; chloroform / 3 h / 20 °C 3.1: diisopropylamine / copper(l) iodide / methanol / 6 h / 45 - 50 °C 4.1: hydrogenchloride; zinc / ethanol; water / 1 h / 70 °C / Heating / reflux 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 5.2: 1 h / -78 - 20 °C 6.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: iodine; sodium hydrogencarbonate / water / 20 °C 2.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran; chloroform / 3 h / 20 °C 3.1: triethylamine / copper(l) iodide / ethanol / 3.5 h / 70 °C 4.1: palladium 10% on activated carbon; cyclohexene / ethanol / 2.5 h / Heating / reflux 5.1: sodium hydroxide / methanol; water / 1.5 h / 20 °C 6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 6.2: 1 h / -78 - 20 °C 7.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 8.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme |
(7-chlorofuro[2,3-c]pyridin-5-yl)methanol
PHA-543613
Conditions | Yield |
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Multi-step reaction with 4 steps 1: 19.5 g / Zn; aq. HCl / ethanol / 1 h / Heating 2: 86 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 3: aq. KH2PO4; sodium chlorite / dimethylsulfoxide 4: diisopropylethylamine; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF6 / dimethylformamide / 3 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: hydrogenchloride; zinc / ethanol; water / 1 h / 70 °C / Heating / reflux 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 2.2: 1 h / -78 - 20 °C 3.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme |
2-chloro-3-hydroxy-6-(hydroxymethyl)-4-iodopyridine
PHA-543613
Conditions | Yield |
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Multi-step reaction with 6 steps 1: 11.4 g / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran; CHCl3 / 3 h / 20 °C 2: CuI; diisopropylamine / methanol / 6 h / 45 - 50 °C 3: 19.5 g / Zn; aq. HCl / ethanol / 1 h / Heating 4: 86 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 5: aq. KH2PO4; sodium chlorite / dimethylsulfoxide 6: diisopropylethylamine; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF6 / dimethylformamide / 3 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran; chloroform / 3 h / 20 °C 2.1: triethylamine / copper(l) iodide / ethanol / 3.5 h / 70 °C 3.1: hydrogenchloride; zinc / ethanol; water / 1 h / 70 °C / Heating / reflux 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 4.2: 1 h / -78 - 20 °C 5.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran; chloroform / 3 h / 20 °C 2.1: diisopropylamine / copper(l) iodide / methanol / 6 h / 45 - 50 °C 3.1: hydrogenchloride; zinc / ethanol; water / 1 h / 70 °C / Heating / reflux 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 4.2: 1 h / -78 - 20 °C 5.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran; chloroform / 3 h / 20 °C 2.1: triethylamine / copper(l) iodide / ethanol / 3.5 h / 70 °C 3.1: palladium 10% on activated carbon; cyclohexene / ethanol / 2.5 h / Heating / reflux 4.1: sodium hydroxide / methanol; water / 1.5 h / 20 °C 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 5.2: 1 h / -78 - 20 °C 6.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme |
2-chloro-6-(hydroxymethyl)-4-[(trimethylsilyl)ethynyl]-3-pyridinol
PHA-543613
Conditions | Yield |
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Multi-step reaction with 5 steps 1: CuI; diisopropylamine / methanol / 6 h / 45 - 50 °C 2: 19.5 g / Zn; aq. HCl / ethanol / 1 h / Heating 3: 86 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 4: aq. KH2PO4; sodium chlorite / dimethylsulfoxide 5: diisopropylethylamine; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF6 / dimethylformamide / 3 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: triethylamine / copper(l) iodide / ethanol / 3.5 h / 70 °C 2.1: hydrogenchloride; zinc / ethanol; water / 1 h / 70 °C / Heating / reflux 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 3.2: 1 h / -78 - 20 °C 4.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: diisopropylamine / copper(l) iodide / methanol / 6 h / 45 - 50 °C 2.1: hydrogenchloride; zinc / ethanol; water / 1 h / 70 °C / Heating / reflux 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 3.2: 1 h / -78 - 20 °C 4.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: triethylamine / copper(l) iodide / ethanol / 3.5 h / 70 °C 2.1: palladium 10% on activated carbon; cyclohexene / ethanol / 2.5 h / Heating / reflux 3.1: sodium hydroxide / methanol; water / 1.5 h / 20 °C 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 4.2: 1 h / -78 - 20 °C 5.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme |
5-hydroxymethyl-2-trimethylsilyl-furo[2,3-c]pyridine
PHA-543613
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: sodium hydroxide / methanol; water / 1.5 h / 20 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C 2.2: 1 h / -78 - 20 °C 3.1: sodium chlorite; potassium dihydrogenphosphate / water; dimethyl sulfoxide / 3 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; HATU / DMF (N,N-dimethyl-formamide) / 2.5 h / 0 - 20 °C View Scheme |