Home Cart 0 Sign in  

[ CAS No. 1279866-58-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1279866-58-8
Chemical Structure| 1279866-58-8
Structure of 1279866-58-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1279866-58-8 ]

Related Doc. of [ 1279866-58-8 ]

Alternatived Products of [ 1279866-58-8 ]

Product Details of [ 1279866-58-8 ]

CAS No. :1279866-58-8 MDL No. :MFCD22209368
Formula : C14H27ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LPRFEBCQOPCLMH-UHFFFAOYSA-N
M.W : 290.83 Pubchem ID :71464197
Synonyms :

Calculated chemistry of [ 1279866-58-8 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.93
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 87.13
TPSA : 41.57 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.57
Log Po/w (WLOGP) : 2.43
Log Po/w (MLOGP) : 2.23
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 1.81

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.251 mg/ml ; 0.000862 mol/l
Class : Soluble
Log S (Ali) : -3.09
Solubility : 0.236 mg/ml ; 0.000811 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.66
Solubility : 0.639 mg/ml ; 0.0022 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.99

Safety of [ 1279866-58-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1279866-58-8 ]

* 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 [ 1279866-58-8 ]

[ 1279866-58-8 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 1279866-58-8 ]
  • [ 1480443-55-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: caesium carbonate / acetonitrile / 0.17 h / 20 °C 1.2: 18 h / Reflux 2.1: triethylamine; {(π-C5H5)2ZrCl} / dichloromethane / 3.5 h / 65 °C
Multi-step reaction with 2 steps 1: caesium carbonate / acetonitrile / 60 °C 2: triethylamine; Schwartz's reagent / 48 h / 20 - 65 °C
Multi-step reaction with 2 steps 1: caesium carbonate / acetonitrile / Reflux 2: triethylamine; zirconocene dichloride / 2-methyltetrahydrofuran / 60 °C
  • 2
  • [ 38771-21-0 ]
  • tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride [ No CAS ]
  • tert-butyl 2-(but-3-ynyl)-2,9-diazaspiro[5.5]undecane-9-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride With caesium carbonate In acetonitrile at 20℃; for 0.166667h; Stage #2: 4-bromobut-1-yne In acetonitrile for 18h; Reflux; 17 Synthesis of tert-butyl 4-but-3-ynyl-4,9-diazaspiro[5.5]undecane-9-carboxylate Scheme 3, step A: Cesium carbonate (46.66 g, 143.21 mmol) is added to a suspension of tert-butyl 4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (16.66 g, 57.28 mmoles) in acetonitrile (167 mL). The mixture is stirred for 10 minutes at ambient temperature then 4-bromobutyne (6.45 mL, 68.74 mmol) is added. The reaction is heated to reflux and stirred for 18 hours. The mixture is cooled and concentrated under reduced pressure. The residue is partitioned between water (200 mL) and ethyl acetate (150 mL). The phases are separated and the aqueous layer is extracted with ethyl acetate (100 mL). The combined organic layers are washed with water (200 mL), then brine (150 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (17.2 g, 98% yield). 1H NMR (300.11 MHz, CDCl3): δ 3.43-3.31 (m, 4H), 2.53-2.48 (m, 2H), 2.37-2.29 (m, 4H), 2.20 (s, 2H), 1.94 (t, J=2.6 Hz, 1H), 1.44 (s, 17H).
98% With caesium carbonate In acetonitrile for 18h; Reflux; 14.3.A tert-butyl 4-but-3-ynyl-4,9-diazaspiro[5.5]undecane-9-carboxylate Cesium carbonate (46.66 g, 143.21 mmol) is added to a suspension of tert-butyl 4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (16.66 g, 57.28 mmoles) in acetonitrile (167 mL). The mixture is stirred for 10 minutes at ambient temperature then 4-bromobutyne (6.45 mL, 68.74 mmol) is added. The reaction is heated to reflux and stirred for 18 hours. The mixture is cooled and concentrated under reduced pressure. The residue is partitioned between water (200 mL) and ethyl acetate (150 mL). The phases are separated and the aqueous layer is extracted with ethyl acetate (100 mL). The combined organic layers are washed with water (200 mL), then brine (150 mL), dried over MgS04, filtered, and concentrated under reduced pressure to give the title compound (17.2 g, 98% yield). lH NMR (300.11 MHz, CDC13): δ 3.43-3.31 (m, 4H), 2.53-2.48 (m, 2H), 2.37-2.29 (m, 4H), 2.20 (s, 2H), 1.94 (t, J= 2.6 Hz, 1H), 1.44 (s, 17H).
72% With caesium carbonate In acetonitrile at 60℃; 7.A tert-butyl 4-but-3-ynyl-4,9-diazaspiro[5.5]undecane-9-carboxylate Scheme 2, step A: A mixture of tert-butyl 4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (170.00 g, 584.53 mmoles), cesium carbonate (476.13 g, 1.46 moles), and 4-bromobutyne (93.28 g, 701.43 mmoles) in acetonitrile (1.70 L) is heated to 60° C. and stirred at this temperature overnight. Further 4-bromobutyne (46.64 g, 350.72 mmoles) is added and the mixture is stirred at 60° C. overnight. The mixture is cooled and filtered. The filtrate is concentrated under reduced pressure and the residue dissolved in ethyl acetate (500 mL), washed with water (1 L), and saturated aqueous sodium chloride (1 L), then dried over MgSO4, and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica column chromatography eluting with 20 to 70% ethyl acetate in dichloromethane to provide the title compound (129 g, 72% yield). Mass spectrum (m/z): 307.25 (M+1).
13.6 g With caesium carbonate In acetonitrile Reflux; 9 Alternative Preparation of Final Title Compound Alternative Preparation of Final Title Compound Add tert-butyl 4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (46.07 mmol) and cesium carbonate (115.2 mmol) to a solution of acetonitrile (200 mL). After stirring at room temperature for 20 minutes, add 4-bromobutyne (69.1 mmol) and heat the mixture to reflux with stirring overnight. Cool to room temperature and dilute with ethyl acetate (200 mL). Filter the reaction through a glass frit rinsing with ethyl acetate (2*100 mL). Concentrate the crude mixture under reduced pressure, then add ethyl acetate (200 mL) and wash the organics with water (200 mL) and brine (200 mL). Dry the organics over sodium sulfate, filter, and concentrate under reduced pressure to yield crude tert-butyl 4-but-3-ynyl-4,9-diazaspiro[5.5]undecane-9-carboxylate (13.6 g, 44.4 mmol): MS (m/z): 307.2 (M+H).

  • 3
  • [ 1480443-25-1 ]
  • [ 1279866-58-8 ]
  • [ 1480443-27-3 ]
YieldReaction ConditionsOperation in experiment
275 mg With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 0.5h; 7 Synthesis of tert-butyl 2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9-diazaspiro[5.5]undecane-9-carboxylate Scheme 1, step G: Add sodium triacetoxyborohydride (98 mg, 0.46 mmol) to a solution of 4-{4-[(1E)-4-oxybut-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside (270 mg, 0.31 mmol) and tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (179 mg, 0.62 mmol) in 1,2-dichloroethane (5 mL). After 30 minutes at room temperature, quench the reaction with saturated aqueous sodium bicarbonate (10 mL). Extract with dichloromethane (30 mL). Wash extract with water (30 mL) and brine (40 mL), dry organic phase over sodium sulfate, filter and concentrate under reduced pressure. Purify the resulting residue by flash chromatography to yield the title compound (275 mg, 0.25 mmol). MS (m/z): 1115.6 (M+1).
275 mg With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 0.5h; 7.1.G tert-butyl 2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-0-benzoyl-beta-D- glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9- diazaspiro[5.5]undecane-9-carboxylate Add sodium triacetoxyborohydride (98 mg, 0.46 mmol) to a solution of 4-{4-[(l£)-4-oxybut-l-en-l-yl]-2-methylbenzyl}-5-(propan-2-yl)-lH-pyrazol- 3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside (270 mg, 0.31 mmol) and tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (179 mg, 0.62 mmol) in 1,2- dichloroethane (5 mL). After 30 minutes at room temperature, quench the reaction with saturated aqueous sodium bicarbonate (10 mL). Extract with dichloromethane (30 mL). Wash extract with water (30 mL) and brine (40 mL), dry organic phase over sodium sulfate, filter and concentrate under reduced pressure. Purify the resulting residue by flash chromatography to yield the title compound (275 mg, 0.25 mmol).
  • 4
  • [ 1279866-58-8 ]
  • [ 1480443-32-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: caesium carbonate / acetonitrile / 0.17 h / 20 °C 1.2: 18 h / Reflux 2.1: triethylamine; {(π-C5H5)2ZrCl} / dichloromethane / 3.5 h / 65 °C 3.1: potassium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-1-propyl-1,1'-biphenyl / tetrahydrofuran; water / 16 h / Inert atmosphere; Reflux 4.1: trifluoroacetic acid / dichloromethane; water / 0.5 h / 20 °C / Cooling with ice
  • 5
  • [ 1279866-58-8 ]
  • [ 1480443-58-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / acetonitrile / 0.17 h / 20 °C 1.2: 18 h / Reflux 2.1: triethylamine; {(π-C5H5)2ZrCl} / dichloromethane / 3.5 h / 65 °C 3.1: potassium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-1-propyl-1,1'-biphenyl / tetrahydrofuran; water / 16 h / Inert atmosphere; Reflux
  • 6
  • [ 1279866-58-8 ]
  • [ 1480443-37-5 ]
  • [ 1480443-39-7 ]
YieldReaction ConditionsOperation in experiment
500 mg With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 0.5h; 12 Synthesis of tert-butyl 2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9-diazaspiro[5.5]undecane-9-carboxylate Scheme 2, Step D: Add sodium triacetoxyborohydride (303 mg, 1.4 mmol) to a solution of 4-{4-[(1E)-4-oxybut-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (600 mg, 0.95 mmol) and tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (333 mg, 1.2 mmol) in 1,2-dichloroethane (30 mL). After 30 minutes at room temperature, quench the reaction with saturated aqueous sodium bicarbonate (15 mL). Extract with dichloromethane (60 mL). Wash extract with water (30 mL) and brine (60 mL). Dry organic phase over sodium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue by flash chromatography to yield the title compound (500 mg, 0.58 mmol). MS (m/z): 866.8, 867.8 (M+1), 864.8, 865.8 (M-1).
500 mg With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 0.5h; 12a.2.D tert-butyl 2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-0-acetyl-beta-D- glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl} -2,9-diazaspiro[5.5]undecane-9-carboxylate Add sodium triacetoxyborohydride (303 mg, 1.4 mmol) to a solution of 4-{4-[(l£)-4-oxybut-l-en-l-yl]-2-methylbenzyl}-5-(propan-2-yl)-lH-pyrazol- 3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (600 mg, 0.95 mmol) and tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (333 mg, 1.2 mmol) in 1,2- dichloroethane (30 mL). After 30 minutes at room temperature, quench the reaction with saturated aqueous sodium bicarbonate (15 mL). Extract with dichloromethane (60 mL). Wash extract with water (30 mL) and brine (60 mL). Dry organic phase over sodium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue by flash chromatography to yield the title compound (500 mg, 0.58 mmol). MS (m/z): 866.8, 867.8 (M+l), 864.8, 865.8 (M-l).
  • 7
  • [ 1279866-58-8 ]
  • [ CAS Unavailable ]
  • [ 1480443-39-7 ]
YieldReaction ConditionsOperation in experiment
630 mg With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; 9.A tert-butyl 2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9-diazaspiro[5.5]undecane-9-carboxylate Scheme 3, step A: Heat a mixture of (3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl methanesulfonate (1.0 g, 1.41 mmol), tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (451 mg, 1.55 mmol), and diisopropylethylamine (730 mg, 5.64 mmol) in acetonitrile (4 mL) at 80° C. overnight. Remove the solvent under the reduced pressure. Purify the resulting residue by flash chromatography (silica gel, gradient ethyl acetate/dichloromethane from 25-85% over 15 min, then with methanol/dichloromethane from 1-3% over 10 min, 40 g column) to provide the title compound (630 mg, 0.73 mmol). MS (m/z): 867.2, 868.4 (M+1), 865.2, 866.4 (M-1).
  • 8
  • [ 1279866-58-8 ]
  • [ 1480443-39-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / acetonitrile / 60 °C 2: triethylamine; Schwartz's reagent / 48 h / 20 - 65 °C 3: potassium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-1-propyl-1,1'-biphenyl / tetrahydrofuran; water / Reflux
  • 9
  • [ 1279866-58-8 ]
  • [ 1480443-45-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / acetonitrile / 60 °C 2: triethylamine; Schwartz's reagent / 48 h / 20 - 65 °C 3: potassium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-1-propyl-1,1'-biphenyl / tetrahydrofuran; water / Reflux 4: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 20 °C
  • 10
  • [ 1279866-58-8 ]
  • [ 1593548-59-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: caesium carbonate / acetonitrile / 60 °C 2: triethylamine; Schwartz's reagent / 48 h / 20 - 65 °C 3: potassium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-1-propyl-1,1'-biphenyl / tetrahydrofuran; water / Reflux 4: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 20 °C 5: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 2 h / 20 °C
  • 11
  • [ 1279866-58-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: caesium carbonate / acetonitrile / 60 °C 2: triethylamine; Schwartz's reagent / 48 h / 20 - 65 °C 3: potassium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-1-propyl-1,1'-biphenyl / tetrahydrofuran; water / Reflux 4: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 20 °C 5: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 2 h / 20 °C 6: hydrogenchloride / dichloromethane; 1,4-dioxane / 4 h / 20 °C
  • 12
  • [ 1279866-58-8 ]
  • [ 1593548-47-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: caesium carbonate / acetonitrile / 60 °C 2.1: triethylamine; Schwartz's reagent / 48 h / 20 - 65 °C 3.1: potassium carbonate; palladium diacetate; 2-(dicyclohexylphosphino)-2',4',6'-tri-1-propyl-1,1'-biphenyl / tetrahydrofuran; water / Reflux 4.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 2 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 2 h / 20 °C 6.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 4 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h 7.2: 0.33 h / 5 °C 7.3: 20 - 40 °C
  • 13
  • [ 1279866-58-8 ]
  • [ 953742-45-5 ]
  • [ 1702300-69-3 ]
YieldReaction ConditionsOperation in experiment
0.38 g With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h; 7 Preparation of Final Title Compound Preparation of Final Title Compound To a round bottom flask add tert-butyl 4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (1.38 mmol), 2-(isobutylcarbamoylamino)acetic acid (1.15 mmol), dimethylformamide (3.8 mL), triethylamine (1.72 mmol), and HATU (1.26 mmol Stir at room temperature for 16 hours, then dilute with water (50 mL) and ethyl acetate (50 mL). Wash the organic phase with concentrated ammonium chloride (50 mL) and brine (50 mL). Dry the organics over sodium sulfate, filter, and concentrate under reduced pressure. Purify the intermediate by flash chromatography (40 g silica gel cartridge) eluting with 0-10% methanol in ethyl acetate to yield tert-butyl 9-12-(isobutylcarbamoylamino)acetyl[-4,9-diazaspiro[5.5]undecane-4-carboxylate (0.38 g, 0.93 mmol): MS (m/z): 411.2 (M+H).
  • 14
  • [ 1279866-58-8 ]
  • [ 1702300-76-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / acetonitrile / Reflux 2: triethylamine; zirconocene dichloride / 2-methyltetrahydrofuran / 60 °C 3: palladium diacetate; potassium carbonate; XPhos / tetrahydrofuran; water / 16 h / 65 °C / Inert atmosphere 4: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C
  • 15
  • [ 1279866-58-8 ]
  • [ 1702300-71-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: caesium carbonate / acetonitrile / Reflux 2.1: triethylamine; zirconocene dichloride / 2-methyltetrahydrofuran / 60 °C 3.1: palladium diacetate; potassium carbonate; XPhos / tetrahydrofuran; water / 16 h / 65 °C / Inert atmosphere 4.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C 5.1: triethylamine / dichloromethane 5.2: 1.75 h
  • 16
  • [ 1279866-58-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: caesium carbonate / acetonitrile / Reflux 2.1: triethylamine; zirconocene dichloride / 2-methyltetrahydrofuran / 60 °C 3.1: palladium diacetate; potassium carbonate; XPhos / tetrahydrofuran; water / 16 h / 65 °C / Inert atmosphere 4.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C 5.1: triethylamine / dichloromethane 5.2: 1.75 h 6.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 4.5 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
  • 17
  • [ 1279866-58-8 ]
  • [ 1702300-77-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: caesium carbonate / acetonitrile / Reflux 2.1: triethylamine; zirconocene dichloride / 2-methyltetrahydrofuran / 60 °C 3.1: palladium diacetate; potassium carbonate; XPhos / tetrahydrofuran; water / 16 h / 65 °C / Inert atmosphere 4.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C 5.1: triethylamine / dichloromethane 5.2: 1.75 h 6.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 4.5 h / 20 °C
  • 18
  • [ 1279866-58-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C 2: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 80 °C
Multi-step reaction with 5 steps 1: caesium carbonate / acetonitrile / Reflux 2: triethylamine; zirconocene dichloride / 2-methyltetrahydrofuran / 60 °C 3: palladium diacetate; potassium carbonate; XPhos / tetrahydrofuran; water / 16 h / 65 °C / Inert atmosphere 4: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C 5: triethylamine / dichloromethane / 0.17 h
  • 19
  • [ 1279866-58-8 ]
  • [ 1702300-67-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C 2: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 20 °C 3.2: 3 h / 20 °C 4.1: 5%-palladium/activated carbon; cyclohexene / ethanol / 0.75 h / Reflux
  • 20
  • [ 1279866-58-8 ]
  • [ 1702300-68-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C 2: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C 3: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 80 °C 4: sodium methylate / methanol / 0.67 h
Multi-step reaction with 6 steps 1: caesium carbonate / acetonitrile / Reflux 2: triethylamine; zirconocene dichloride / 2-methyltetrahydrofuran / 60 °C 3: palladium diacetate; potassium carbonate; XPhos / tetrahydrofuran; water / 16 h / 65 °C / Inert atmosphere 4: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C 5: triethylamine / dichloromethane / 0.17 h 6: sodium methylate / methanol / 0.67 h
Multi-step reaction with 8 steps 1.1: caesium carbonate / acetonitrile / Reflux 2.1: triethylamine; zirconocene dichloride / 2-methyltetrahydrofuran / 60 °C 3.1: palladium diacetate; potassium carbonate; XPhos / tetrahydrofuran; water / 16 h / 65 °C / Inert atmosphere 4.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 3 h / 20 °C 5.1: triethylamine / dichloromethane 5.2: 1.75 h 6.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 4.5 h / 20 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 8.1: sodium hydrogencarbonate / water
  • 21
  • [ 1279866-58-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / acetonitrile / Reflux 2: triethylamine; zirconocene dichloride / 2-methyltetrahydrofuran / 60 °C 3: palladium diacetate; potassium carbonate; XPhos / tetrahydrofuran; water / 16 h / 65 °C / Inert atmosphere
  • 22
  • [ 1279866-58-8 ]
  • [ 501-53-1 ]
  • [ 1452809-16-3 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0 - 20℃; 10c Preparation of O4-benzyl O9-tert-butyl 4,9-diazaspiro[5.5]undecane-4,9-dicarboxylate Preparation of O4-benzyl O9-tert-butyl 4,9-diazaspiro[5.5]undecane-4,9-dicarboxylate To a 20 L temperature controlled reactor charge tert-butyl 4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (2.06 moles; 600.00 g) followed by dichloromethane (6.00 L), then triethylamine (4.33 moles; 604 mL) is added. Set the jacket of the reactor to 0° C. When the temperature of the reaction mixture reaches 5° C., add benzyl chloroformate (2.10 moles; 311 mL) over about 20 minutes keeping the internal temperature below 20° C. When the addition is complete, warm the jacket to room temperature and stir the mixture overnight. Pour the reaction mixture into water (4 L) and separate the mixture. Concentrate the organics under reduced pressure to give the title compound (838 g; assumed 95.65% purity and 100% yield for the purposes of calculation in the next reaction) mass spectrum (m/z): 411.2 (M+23).
  • 23
  • [ 1279866-58-8 ]
  • [ 1714144-99-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 20 °C 3.2: 3 h / 20 °C 4.1: 5%-palladium/activated carbon; cyclohexene / ethanol / 0.75 h / Reflux 5.1: potassium carbonate; potassium iodide / acetonitrile / Reflux; Inert atmosphere 5.2: 1 h / 20 °C
  • 24
  • [ 1279866-58-8 ]
  • [ 2841567-53-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: hydrogenchloride / 1,4-dioxane / 5 - 20 °C
  • 25
  • [ 1279866-58-8 ]
  • [ 1714144-92-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 20 °C 3.2: 3 h / 20 °C
  • 26
  • [ 1279866-58-8 ]
  • [ 1714144-93-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 20 °C 3.2: 3 h / 20 °C 4.1: 5%-palladium/activated carbon; cyclohexene / ethanol / 0.75 h / Reflux 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 80 °C 5.2: 1 h / 20 °C
Multi-step reaction with 6 steps 1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: hydrogenchloride / 1,4-dioxane / 5 - 20 °C 3.1: 1,1'-carbonyldiimidazole / dichloromethane / 1 h / 20 °C 3.2: 3 h / 20 °C 4.1: 5%-palladium/activated carbon; cyclohexene / ethanol / 0.75 h / Reflux 5.1: potassium carbonate; potassium iodide / acetonitrile / Reflux; Inert atmosphere 5.2: 1 h / 20 °C 6.1: sodium methylate; methanol / 0.17 h / Cooling with ice
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 1279866-58-8 ]

Amides

Chemical Structure| 851325-42-3

[ 851325-42-3 ]

tert-Butyl 2,8-diazaspiro[4.5]decane-8-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 1624261-87-5

[ 1624261-87-5 ]

tert-Butyl 1-(aminomethyl)-6-azaspiro[2.5]octane-6-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 929302-18-1

[ 929302-18-1 ]

tert-Butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 1023301-84-9

[ 1023301-84-9 ]

tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 236406-22-7

[ 236406-22-7 ]

1-Boc-4-(Aminomethyl)-4-methylpiperidine

Similarity: 0.98

Related Parent Nucleus of
[ 1279866-58-8 ]

Aliphatic Heterocycles

Chemical Structure| 851325-42-3

[ 851325-42-3 ]

tert-Butyl 2,8-diazaspiro[4.5]decane-8-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 1624261-87-5

[ 1624261-87-5 ]

tert-Butyl 1-(aminomethyl)-6-azaspiro[2.5]octane-6-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 929302-18-1

[ 929302-18-1 ]

tert-Butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 1023301-84-9

[ 1023301-84-9 ]

tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 236406-22-7

[ 236406-22-7 ]

1-Boc-4-(Aminomethyl)-4-methylpiperidine

Similarity: 0.98

Piperidines

Chemical Structure| 851325-42-3

[ 851325-42-3 ]

tert-Butyl 2,8-diazaspiro[4.5]decane-8-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 1624261-87-5

[ 1624261-87-5 ]

tert-Butyl 1-(aminomethyl)-6-azaspiro[2.5]octane-6-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 929302-18-1

[ 929302-18-1 ]

tert-Butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 1023301-84-9

[ 1023301-84-9 ]

tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 236406-22-7

[ 236406-22-7 ]

1-Boc-4-(Aminomethyl)-4-methylpiperidine

Similarity: 0.98

Spiroes

Chemical Structure| 851325-42-3

[ 851325-42-3 ]

tert-Butyl 2,8-diazaspiro[4.5]decane-8-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 1624261-87-5

[ 1624261-87-5 ]

tert-Butyl 1-(aminomethyl)-6-azaspiro[2.5]octane-6-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 929302-18-1

[ 929302-18-1 ]

tert-Butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 1023301-84-9

[ 1023301-84-9 ]

tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 189333-03-7

[ 189333-03-7 ]

tert-Butyl 2,9-diazaspiro[5.5]undecane-2-carboxylate

Similarity: 0.98