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[ CAS No. 192130-34-0 ] {[proInfo.proName]}

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Chemical Structure| 192130-34-0
Chemical Structure| 192130-34-0
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Product Details of [ 192130-34-0 ]

CAS No. :192130-34-0 MDL No. :MFCD02683049
Formula : C11H23N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QSYTWBKZNNEKPN-UHFFFAOYSA-N
M.W : 229.32 Pubchem ID :1514400
Synonyms :
Chemical Name :tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylate

Calculated chemistry of [ 192130-34-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.91
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 70.92
TPSA : 58.8 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.64
Log Po/w (XLOGP3) : -0.02
Log Po/w (WLOGP) : -0.26
Log Po/w (MLOGP) : 0.32
Log Po/w (SILICOS-IT) : -0.01
Consensus Log Po/w : 0.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.92
Solubility : 27.6 mg/ml ; 0.12 mol/l
Class : Very soluble
Log S (Ali) : -0.77
Solubility : 39.4 mg/ml ; 0.172 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.02
Solubility : 21.9 mg/ml ; 0.0955 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.48

Safety of [ 192130-34-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 192130-34-0 ]

* 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 [ 192130-34-0 ]

[ 192130-34-0 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 192130-34-0 ]
  • [ 156090-03-8 ]
  • [ 220073-86-9 ]
  • 2
  • 3-(4-oxo-bicyclo[3.1.0]hex-1-yl)benzonitrile [ No CAS ]
  • [ 192130-34-0 ]
  • 4-{2-[(1R,2S,5R)-5-(3-Cyano-phenyl)-bicyclo[3.1.0]hex-2-ylamino]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • 3
  • 5-chloro-2-{1-[2-(3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethyl]-piperidin-4-yl}-benzoic acid trifluoroacetate [ No CAS ]
  • [ 192130-34-0 ]
  • 4-[2-(5-chloro-2-{1-[2-(3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethyl]-piperidin-4-yl}-benzoylamino)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With 4-methyl-morpholine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; A solution of Compound 4-7 (0.24 g, 0.58 mmol) in dimethylformamide (3 mL) was combined with N-methylmorpholine (0.19 mL, 1.74 mmol), 1-hydroxybenzotriazole (0.04 g, 0.29 mmol), O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU, 0.26 g, 0.70 mmol) and Compound 4-8 (0.16 g, 0.70 mmol). The reaction mixture was stirred overnight at rt, quenched with saturated ammonium chloride, and extracted with ethylacetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by RP HPLC (gradient elution with 10-60percent acetonitrile in water, each with 0.1percent TFA) and lyophilized to yield Compound 66 as white solid (trifluoroacetate salt, 0.26 g, 72percent). 1H NMR (300 MHz, DMSO) delta 7.58-7.53 (m, 2H), 7.37 (d, J=8.5 Hz, 1H), 7.30 (m, 1H), 7.12-7.05 (m, 3H), 4.70 (s, 2H), 4.3-3.1 (m, 21H), 2.0-1.8 (m, 4H), 1.42 (s, 9H); MS (ES+) m/z 626.1 (M+1); Anal Calcd. for C33H44ClN5O5-3.6CF3CO2H: C, 46.58; H, 4.63; N, 6.76. Found: C, 46.25, H, 4.48; N, 6.73.
  • 4
  • [ 192130-34-0 ]
  • tert-butyl 4-(2-{2-[6-chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydrobenzimidazol-1-yl]-2-phenylacetylamino}ethyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Example 130; tert-Butyl 4-(2-{2-[6-chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3- dihydrobenzimidazol-1 -yl]-2-phenylacetylamino}ethyl)piperazine-1 -carboxylate; 474 mg (1.00 mmol) of 6-chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3- dihydrobenzimidazol-1-yl]phenylacetic acid (XIIIa), 204 mg (1.50 mmol) of HOBt and <n="136"/>850 mg (1.10 mmol) of solid phase-bound PS-carbodiimide (Argonaut, 1.3 mmol/g) were dissolved in 10 ml of dry dichloromethane in a screw-cap tube and checked mechanically at room temperature for 10 min. 241 mg (1.05 mmol) of 1-Boc-(2- aminoethyl)piperazine were added, and the mixture was then checked mechanically overnight. Three equivalents of solid phase-bound MP-carbonate were then added to the reaction mixture, and checking was continued for 2 h. The solid phase-bound reagents were filtered off and washed with dichloromethane. The filtrate was concentrated in vacuo, and the residue was dried in vacuo. The residue was purified by chromatography on silica gel (mobile phase gradient 0.5-5percent methanol in dichloromethane). Yield: 574 mg (84percent) of colorless oil.1H-NMR (methanol-d4): 1.46 (s, 9H), 2.28-2.52 (m, 6H), 3.32-3.50 (m, 6H), 3.89 (s, 3H), 6.20 (s, 1 H), 6.80 (s, 1 H), 7.07-7.14 (m, 3H), 7.24-7.38 (m, 5H), 7.86 (d, J = 8.6 Hz, 1 H), 8.01 (d, J = 8.8 Hz, 2H). MS (API-ES, pos) m/z = 684, 686 [M+H]+
  • 5
  • [ 877058-70-3 ]
  • [ 192130-34-0 ]
  • [ 877058-71-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 20 - 130℃; for 15.25h; A vial was charged with palladium (II) acetate (0.012 g, 0.054 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.034 g, 0.054 mmol). Toluene (1.0 mL) was added and the system was flushed with argon. The vial was capped and the mixture stirred at room temperature for 15 min. A resealable tube was charged with 4-(4-chloro-3-phenyl-furo[2,3-b]pyridin-2-yl)-phenol (6) (0.174 g, 0.541 mmol), 4-N-(tert-butoxycarbonyl)-1-aminoethylpiperazine (0.248 g, 1.08 mmol), and potassium carbonate (1.495 g, 10.82 mmol). The Pd/BINAP solution was added along with 1.0 mL of toluene, and the system was flushed with argon. The tube was sealed and the mixture stirred at 130 C. for 15 h. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford a brown solid. This material was purified via column chromatography on silica gel (eluting with 0-50% (90:10:1, dichloromethane/methanol/ammonium hydroxide)-dichloromethane) to afford 4-{2-[2-(4-hydroxy-phenyl)-3-phenyl-furo[2,3-b]pyridin-4-ylamino]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester 7a as a tan solid. MS (MH+) 515.2; Calculated 514 for C30H34N4O4.
  • 6
  • [ 937789-88-3 ]
  • [ 192130-34-0 ]
  • [ 937789-89-4 ]
  • 7
  • [ 1000771-68-5 ]
  • [ 192130-34-0 ]
  • C33H44ClN5O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With hydrazine hydrate; In ethanol; for 24h;Reflux; General procedure: Example 4 Production of 2-(4-Cyclohexylpiperazin-1-yl)ethylamine. Hydrazine monohydrate (0.8 g, 16 mmol) was added to an ethanol (30 mL) solution of the compound obtained in Example 3 (2.8 g, 8.2 mmol) at room temperature, and the mixture was heated under refluxing for 24 hours. The precipitated crystals were filtered away, and the solvent of the filtrate was distilled off under a reduced pressure. The residue was purified with silica gel column chromatography (chloroform : methanol = 95:5), to give the captioned compound (1.3 g, 75percent) as an oily product. 1H-NMR (DMSO-d6) delta: 1.05-1.17 (m, 5H), 1.53-1.55 (m, 1H), 1.68-1.71 (m, 4H), 2.11-2.13 (m, 1H), 2.30-2.45 (m 7H), 2.48-2.51 (m, 3H), 3.67 (t, J=6.6 Hz, 2H).
Following the procedure of Example 6, and substituting the following for N,N-dimethylethylenediamine:...1-(2-aminoethyl)-4-phenylpiperidine,1-(2-aminoethyl)-2,6-dimethylpiperidine,1-(2-aminoethyl)-4-hydroxy-4-phenylpiperidine,1-(2-aminoethyl)-4-phenyl-1,2,3,6-tetrahydropyridine,1-(2-aminoethyl)-4-tertiarybutoxycarbonylpiperazine,1-(2-aminoethyl)-4-methylpiperazine,1-(2-aminoethyl)-4-phenylpiperazine,1-(2-aminoethyl)-4-(phenylmethyl)-piperazine, and...
When in the procedure of Example 20 the following are reacted with 3-phenoxypyrrolidinecarbonyl chloride:N-(2-aminoethyl)morpholine,N-(2-aminoethyl)pyrrolidine,N-(2-aminoethyl)piperidine,1-(2-aminoethyl)-4-methylpiperazine, and1-(2-aminoethyl)-4-(t-butoxycarbonyl)piperazine,
  • 9
  • [ 75-86-5 ]
  • [ 192130-34-0 ]
  • C15H28N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 20℃; for 2h;molecular sieve 3 A; 687 g of 4-amino-2-(trifluoromethyl)benzonitrile with 311 mul of thiophosgene in 4 ml of N,N-dimethylformamide was stirred for one hour at room temperature under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, washed with water and then concentrated by evaporation in a vacuum. The thus obtained crude isothiocyanate was combined with the cyanoamine that was produced and filtered by two hours of stirring from 743 mul of acetone cyanohydrin with 930 mg of 1,1-dimethylethyl 4-(2-aminoethyl)piperazine-1-carboxylate and 406 mg of a molecular sieve 3 A in 20 ml of tetrahydrofuran at room temperature, and it was heated to boiling for one hour with 0.57 ml of triethylamine in 40 ml of tetrahydrofuran. After concentration by evaporation in a vacuum, the title compound was obtained as a crude product, which was immediately further reacted.
  • 10
  • N-(5-tert-butylisoxazol-3-yl)-N-{3-[(2-chloropyrimidin-5-yl)ethynyl]phenyl}urea [ No CAS ]
  • [ 192130-34-0 ]
  • C31H40N8O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In diethyl ether; acetonitrile; at 70℃; for 4h; N-(5-tert-Butylisoxazol-3-yl)-N- {3- [ (2-chloropyrimidin-5-yl) ethynyl] phenyl} urea (Intermediate 9) (0.22 g) and tert-butyl 4-(2-aminoethyl)-piperazine-1-carboxylate (0.38 g) were stirred in MeCN (10 mL) and hydrogen chloride (I. OM solution in ether) (0.11 mL) was added dropwise. The reaction mixture was stirred and heated at 70°C for 4 hours. The solvent was evaporated and the residue was dissolved in DCM (20 mL) and TFA (10 mL). The reaction mixture was stirred at ambient temperature for 2 hours, the solvent was evaporated and the product was purified by flash chromatography on silica using 1-20percent (7N NH3 in MeOH) in DCM as eluent. The product was triturated with ether to give the title compound as an off-white solid (274 mg, 99percent); 'H NMR (DMSO-d6) 1.29 (s, 9H), 2.45-2. 57 (m, 2H), 2.57-2. 65 (m, 4H), 3.03-3. 10 (m, 4H), 3.39-3. 49 (m, 2H), 6.49 (s, 1H), 7.10-7. 16 (m, 1H), 7.29-7. 35 (m, 2H), 7.51 (t, 1H), 7.75 (s, 1H), 8.40-8. 52 (m, 3H), 8.99 (s, 1H), 9.62 (s, 1H) ; MS m/e MH+ 489.
  • 11
  • [ 124-63-0 ]
  • [ 192130-34-0 ]
  • [ 870007-78-6 ]
YieldReaction ConditionsOperation in experiment
70% With pyridine; for 12h; EXAMPLE 24; N-(2-methanosulfonylethyl)-piperazine hydrochloride; Methanesulfonyl chloride (0.7 mL, 9.0 mmol) was added to a cooled solution of <strong>[192130-34-0]4-(2-amino-ethyl)-piperazine-1-carboxylic acid tert-butyl ester</strong> (1.33 g, 5.8 mmol) in pyridine (25.0 mL). The reaction was stirred for 12 h and partitioned between partitioned between aqueous sodium bicarbonate and methylene chloride. The organic phase was washed with 1 M hydrochloric acid, aqueous sodium bicarbonate, and brine, dried over anhydrous magnesium sulfate and concentrated. Purification of the crude residue by chromatography over silica gel using 0-5percent methanol in methylene chloride gave 4-(2-methanesulfonylamino-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (0.70 g, 70percent).
70% With pyridine; for 12h; EXAMPLE43 N-(2-{4-[(4S,5R)-4,5-Bis-(4-chloro-phenyl)-2-(3-ethoxy-thiophen-2-yl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-ethyl)-methanesulfonamide; Methanesulfonyl chloride (0.7 mL, 9.0 mmol) was added to a cooled solution of <strong>[192130-34-0]4-(2-amino-ethyl)-piperazine-1-carboxylic acid tert-butyl ester</strong> (1.33 g, 5.8 mmol) in pyridine (25.0 mL). The reaction was stirred for 12 h and partitioned between partitioned between aqueous sodium bicarbonate and methylene chloride. The organic phase was washed with 1M hydrochloric acid, aqueous sodium bicarbonate, brine, dried over anhydrous magnesium sulfate and concentrated. Purification of the crude residue by flash chromatography over silica gel using 0-5percent methanol in methylene chloride gave 4-(2-methanesulfonylamino-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (0.70 g, 70percent).
70% With pyridine; for 12h; Methanesulfonyl chloride (0.7 mL, 9.0 mmol) was added to a cooled solution of 4-(2-amino- ethyl)-piperazine-1-carboxylic acid tert-butyl ester (1.33 g, 5.8 mmol) in pyridine (25.0 mL). The reaction was stirred for 12 h and partitioned between partitioned between aqueous sodium bicarbonate and methylene chloride. The organic phase was washed with 1M hydrochloric acid, aqueous sodium bicarbonate, brine, dried over anhydrous magnesium sulfate and concentrated. Purification of the crude residue by chromatography over silica gel using 0-5percent methanol in methylene chloride gave 4-(2-methanesulfonylamino-ethyl)-piperazine-l- carboxylic acid tert-butyl ester (0.70 g, 70percent). To a cooled solution of 4-(2-methanesulfonylamino-ethyl)-piperazine- I -carboxylic acid tert- butyl ester (0.64 g, 0.2 mmol) in dioxane (20 mL) was added hydrochloric acid (4M in dioxane, 10 mL) and the reaction was stirred at room temperature for 12 h and concentrated to give N- (2-methanosulfonylethyl) -piperazine dihydrochloride as a white solid (0.55 g, 95percent).
  • 12
  • [ 877058-77-0 ]
  • [ 192130-34-0 ]
  • [ 877058-78-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 20 - 130℃; for 2.25h; A resealable tube was charged with 4-chloro-2-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-3-phenyl-furo[2,3-b]pyridine 6c (0.048 g, 0.110 mmol), 4-N-(tert-butoxycarbonyl)-1-aminoethylpiperazine 9a (0.051 g, 0.221 mmol), and potassium carbonate (0.304 g, 2.20 mmol). The Pd/BINAP solution was added along with 1.5 mL of toluene, and the system was flushed with argon. The tube was sealed and the mixture stirred at 130° C. for 2 h. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford an orange brown oil. This oil was purified via preparative thin layer chromatography (eluting twice with 95:5:0.5, dichloromethane/methanol/ammonium hydroxide) to afford 4-(2-{2-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-3-phenyl-furo[2,3-b]pyridin-4-ylamino}-ethyl)-piperazine-1-carboxylic acid tert-butyl ester 10d as an off white solid. MS (MH+) 628.1; Calculated 627 for C36H45NO5.
  • 13
  • [ 877058-84-9 ]
  • [ 192130-34-0 ]
  • tert-butyl 4-(2-(2-(3-fluoro-4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-phenylfuro[2,3-b]pyridin-4-ylamino)ethyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 20 - 130℃; for 20.25h; A resealable tube was charged with 4-chloro-2-(3-fluoro-4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-phenylfuro[2,3-b]pyridine 6e (0.096 g, 0.213 mmol), 4-N-(tert-butoxycarbonyl)-1-aminoethylpiperazine (0.098 g, 0.426 mmol), potassium carbonate (0.589 g, 4.26 mmol), and toluene (3 mL). The Pd/BINAP solution was added along with 1.5 mL of toluene, and the system was flushed with argon. The tube was sealed and the mixture stirred at 130° C. for 20 h. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford an orange brown oil. This oil was purified via preparative thin layer chromatography (eluting with 95:5:0.5, dichloromethane/methanol/ammonium hydroxide) to afford tert-butyl 4-(2-(2-(3-fluoro-4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-phenylfuro[2,3-b]pyridin-4-ylamino)ethyl)piperazine-1-carboxylate (not shown) as a yellow oil. MS (MH+) 644.4; Calculated 643 for C37H46FN5O4.
  • 14
  • [ 877059-14-8 ]
  • [ 192130-34-0 ]
  • tert-butyl 4-(2-(2-(4-(benzyloxy)phenyl)-5-cyano-3-phenylfuro[2,3-b]pyridin-4-ylamino)ethyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In butan-1-ol; at 100℃; for 24h; To a mixture of 6j (0.812 g, 1.86 mmol, 1.0 equiv) in n-BuOH (30 mL) was added tert-butyl-4-(2-aminoethyl)piperazine-1-carboxylate (2.80 g, 13.0 mmol, 7.0 equiv). After heating at 100° C. for 24 hrs, the solvent was removed in vacuo. The resulting residue was purified by silica gel chromatography (5percent MeOH:CH2C12) to afford carbamate 8c. MS (MH+) 630.1; Calculated 629.3 for C38H39N5O4.
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