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[ CAS No. 57260-73-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 57260-73-8
Chemical Structure| 57260-73-8
Chemical Structure| 57260-73-8
Structure of 57260-73-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 57260-73-8 ]

CAS No. :57260-73-8 MDL No. :MFCD00191871
Formula : C7H16N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :AOCSUUGBCMTKJH-UHFFFAOYSA-N
M.W : 160.21 Pubchem ID :187201
Synonyms :
PROTAC Linker 22
Chemical Name :tert-Butyl (2-aminoethyl)carbamate

Calculated chemistry of [ 57260-73-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.98
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : -0.01
Log Po/w (WLOGP) : 0.47
Log Po/w (MLOGP) : 0.3
Log Po/w (SILICOS-IT) : -0.27
Consensus Log Po/w : 0.47

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.5
Solubility : 51.0 mg/ml ; 0.318 mol/l
Class : Very soluble
Log S (Ali) : -0.89
Solubility : 20.5 mg/ml ; 0.128 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.27
Solubility : 8.6 mg/ml ; 0.0537 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 57260-73-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 57260-73-8 ]

* 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.

  • Upstream synthesis route of [ 57260-73-8 ]
  • Downstream synthetic route of [ 57260-73-8 ]

[ 57260-73-8 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 57260-73-8 ]
  • [ 74-88-4 ]
  • [ 122734-32-1 ]
Reference: [1] Patent: US6903085, 2005, B1, . Location in patent: Page/Page column 77
  • 2
  • [ 57260-73-8 ]
  • [ 122734-32-1 ]
Reference: [1] Patent: US2011/262355, 2011, A1,
[2] Patent: WO2011/133149, 2011, A1,
[3] Patent: WO2011/133150, 2011, A1,
[4] Patent: WO2016/146651, 2016, A1,
[5] Patent: JP2016/41698, 2016, A,
  • 3
  • [ 1722-12-9 ]
  • [ 57260-73-8 ]
  • [ 584-08-7 ]
  • [ 137583-05-2 ]
Reference: [1] Patent: US6159964, 2000, A,
  • 4
  • [ 57260-73-8 ]
  • [ 100-52-7 ]
  • [ 174799-52-1 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: at 20℃; Molecular sieve
Stage #2: at -10 - 20℃; for 16 h;
Preparation 63
Synthesis of tert-butyl 2-(benzylamino)ethylcarbamate (A)
To a solution of tert-butyl 2-aminoethylcarbamate (6.4 g, 40.0 mmol) in methanol (60 mL) was added benzaldehyde (4.7 g, 44.0 mmol) and molecular sieve 3 Å.
After stirring at ambient temperature overnight, the mixture was cooled down to ca. -10° C. (ice/salt bath) and treated portion wise with NaBH4 (9.1 g, 240.0 mmol) over 30 min.
After complete addition, the bath was removed and the reaction mixture stirred at ambient temperature for 16 h.
The solvent was evaporated and the residue taken into EtOAc (150 mL) and poured into water (100 mL).
The organic layer was extracted with 0.5 N HCl (3*100 mL).
The combined aqueous solution was cooled to 0° C., basified with sat.
NaHCO3 and extracted with CHCl3 (3*100 mL).
The combined organic layers were washed with brine (200 mL).
After drying over MgSO4 and filtering, the solvent was evaporated in vacuo to give compound A (9.2 g, 36.8 mmol, 92percent) as a colorless oil. LC-MS [M+H] 251.2 (C14H22N2O2+H, calc: 251.3). TLC Rf (DCM/MeOH 9:1): 0.30.
92%
Stage #1: at 20℃; molecular sieve 3Å
Stage #2: at -10 - 20℃; for 16.5 h;
Example 34: Synthesis of N-((S)-l-{2-[(Dihydrocodein-6-enyloxycarbonyl)-methylamino]- ethylcarbamoyl-4-guanidino}-butyl)-malonamic acid (Compound KC-4)Preparation 63: Synthesis of tert-butyl 2-(benzylamino)ethylcarbamate (A)To a solution of tert-butyl 2-aminoethylcarbamate (6.4 g, 40.0 mmol) in methanol (60 mL) was added benzaldehyde (4.7 g, 44.0 mmol) and molecular sieve 3A. After stirring at ambient temperature overnight, the mixture was cooled down to ca. -10 °C (ice/salt bath) and treated portion wise with NaBH4 (9.1 g, 240.0 mmol) over 30 min. After complete addition, the bath was removed and the reaction mixture stirred at ambient temperature for 16 h. The solvent was evaporated and the residue taken into EtOAc (150 mL) and poured into water (100 mL). The organic layer was extracted with 0.5 N HC1 (3 x 100 mL). The combined aqueous solution was cooled to 0 °C, basified with sat. NaHC03 and extracted with CHC13 (3 x 100 mL). The combined organic layers were washed with brine (200 mL). After drying over MgS04 and filtering, the solvent was evaporated in vacuo to give compound A (9.2 g, 36.8 mmol, 92percent) as a colorless oil. LC-MS [M+H] 251.2 (C14H22N2O2 +H, calc: 251.3). TLC Rf (DCM/MeOH 9:1): 0.30. Compound A was used without further purification.
92%
Stage #1: at 20℃; Molecular sieve 3 Å
Stage #2: With sodium tetrahydroborate In methanol at -10 - 20℃; for 16.5 h; Cooling with ice
Preparation 63: Synthesis of tert-butyl 2-(benzylamino)ethylcarbamate (A)To a solution of tert-butyl 2-aminoethylcarbamate (6.4 g, 40.0 mmol) in methanol (60 mL) was added benzaldehyde (4.7 g, 44.0 mmol) and molecular sieve 3A. After stirring at ambient temperature overnight, the mixture was cooled down to ca. -10 °C (ice/salt bath) and treated portion wise with NaBH4 (9.1 g, 240.0 mmol) over 30 min. After complete addition, the bath was removed and the reaction mixture stirred at ambient temperature for 16 h. The solvent was evaporated and the residue taken into EtOAc (150 mL) and poured into water (100 mL). The organic layer was extracted with 0.5 N HC1 (3 x 100 mL). The combined aqueous solution was cooled to 0 °C, basified with sat. NaHC03 and extracted with CHC13 (3 x 100 mL). The combined organic layers were washed with brine (200 mL). After drying over MgS04 and filtering, the solvent was evaporated in vacuo to give compound A (9.2 g, 36.8 mmol, 92percent) as a colorless oil. LC-MS [M+H] 251.2 (C14H22N2O2 +H, calc: 251.3). TLC Rf (DCM/MeOH 9:1): 0.30. Compound A was used without further purification.
92%
Stage #1: at 20℃; Molecular sieve
Stage #2: at -10 - 20℃; for 16.5 h;
To a solution of tert-butyl 2-aminoethylcarbamate (6.4 g, 40.0 mmol) in methanol (60 mL), Benzaldehyde (4.7 g, 44.0 mmol)And molecular sieves 3 Å were added.After stirring overnight at ambient temperature, the mixture was cooled to about -10 ° C. (ice / salt bath) and treated in portions with NaBH 4 (9.1 g, 240.0 mmol) for 30 minutes. After all addition, the bathtub was removed and the reaction mixture was stirred at ambient temperature for 16 hours. The solvent was evaporated and the residue was taken up in EtOAc (150 mL) and poured into water (100 mL). The organic layer was extracted with 0.5 N HCl (3 × 100 mL). The combined aqueous solution was cooled to 0 ° C., basified with saturated NaHCO 3 and extracted with CHCl 3 (3 × 100 mL). The combined organic layers were washed with brine (200 mL). After drying and filtering over MgSO 4, the solvent was evaporated under reduced pressure to give compound A (9.2 g, 36.8 mmol, 92percent) as a colorless oil.
51%
Stage #1: at 20℃; for 2 h;
Stage #2: at 0 - 20℃;
Example 3Atert-butyl [2-(benzylamino)ethyl]carbamate; 2.0 g (18.4 mmol) benzaldehyde and 3.32 g (20.7 mmol) N-Boc-ethylendiamine are dissolved in 25 ml methanol. The mixture is stirred 2 h at rt before cooled to 00C and 3.57 g (94.2 mmol) sodium borohydride and water are added to generate a solution, which is stirred over night at rt. Solvents are removed in vacuo and the residue is dissolved in dichloromethane and washed with brine, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by reverse phase HPLC (water / acetonitrile) to afford 2.4 g (51percent of th.) of the title compound.HPLC (method 1): R, = 3.70 min; MS (ESIpos): m/z = 251 (M+H)+1H-NMR (400 MHz, DMSOd6): δ = 7.30 (m, 4H), 7.21 (m, IH), 6.72 (m, IH), 3.68 (s, 2H), 3.02 (m, 2H), 2.53 (m, 2H), 2.08 (bs, IH), 1.37 (s, 9H).
23%
Stage #1: With sodium tris(acetoxy)borohydride; magnesium sulfate; triethylamine In 1,2-dichloro-ethane at 20℃; for 16 h;
Stage #2: With water; sodium hydrogencarbonate In 1,2-dichloro-ethane
To a solution of tert-butyl 2-aminoethylcarbamate (3.7 g, 22.3 mmol), benzaldehyde (2.36 g, 22.3 mmol) and MgSO4 (1.33 g) in 1,2-dicholoroethane (300 mL) and Et3N (3.1 mL, 22.3 mmol) at RT was added NaHB(AcO)3. The mixture was stirred (RT, 16 h) and filtered. The solution was washed with saturated NaHCO3 (200 ml), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with MeOH-DCM (0-10percent) to afford tert-butyl 2-(benzylamino)ethylcarbamate (1.4 g, 23percent). Mass calculated for C14H22N2O2=250.34; found: [M+H]+=251.3.

Reference: [1] Patent: US2011/262355, 2011, A1, . Location in patent: Page/Page column 135
[2] Patent: WO2011/133149, 2011, A1, . Location in patent: Page/Page column 297-298
[3] Patent: WO2011/133150, 2011, A1, . Location in patent: Page/Page column 299-300
[4] Patent: JP2016/41698, 2016, A, . Location in patent: Paragraph 0364; 0375
[5] Chemical Communications, 2016, vol. 52, # 63, p. 9837 - 9840
[6] Journal of Medicinal Chemistry, 2005, vol. 48, # 22, p. 7024 - 7039
[7] Patent: WO2007/17092, 2007, A1, . Location in patent: Page/Page column 22
[8] Patent: US2010/41748, 2010, A1, . Location in patent: Page/Page column 120
[9] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 411 - 416
[10] Organic Letters, 2014, vol. 16, # 24, p. 6366 - 6369
[11] Synthesis (Germany), 2015, vol. 47, # 16, p. 2391 - 2406
[12] Patent: US2016/168138, 2016, A1, . Location in patent: Paragraph 0120-0121
[13] Journal of Organic Chemistry, 2016, vol. 81, # 19, p. 8696 - 8709
  • 5
  • [ 57260-73-8 ]
  • [ 174799-52-1 ]
Reference: [1] Patent: US2011/262359, 2011, A1,
  • 6
  • [ 57260-73-8 ]
  • [ 100-39-0 ]
  • [ 174799-52-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 117 - 125
  • 7
  • [ 57260-73-8 ]
  • [ 75-07-0 ]
  • [ 113283-93-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 248 - 262
  • 8
  • [ 57260-73-8 ]
  • [ 39684-80-5 ]
  • [ 117499-16-8 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S498 - S500
  • 9
  • [ 57260-73-8 ]
  • [ 141743-15-9 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 411 - 416
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