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[ CAS No. 51644-96-3 ] {[proInfo.proName]}

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Chemical Structure| 51644-96-3
Chemical Structure| 51644-96-3
Structure of 51644-96-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 51644-96-3 ]

CAS No. :51644-96-3 MDL No. :MFCD00210020
Formula : C10H22N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DPLOGSUBQDREOU-UHFFFAOYSA-N
M.W : 202.29 Pubchem ID :4352
Synonyms :
PROTAC Linker 23

Calculated chemistry of [ 51644-96-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 8
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 57.41
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 1.06
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 1.26
Log Po/w (SILICOS-IT) : 0.97
Consensus Log Po/w : 1.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.23
Solubility : 11.8 mg/ml ; 0.0583 mol/l
Class : Very soluble
Log S (Ali) : -2.0
Solubility : 2.01 mg/ml ; 0.00994 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.5
Solubility : 0.637 mg/ml ; 0.00315 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.12

Safety of [ 51644-96-3 ]

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 [ 51644-96-3 ]

* 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 [ 51644-96-3 ]
  • Downstream synthetic route of [ 51644-96-3 ]

[ 51644-96-3 ] Synthesis Path-Upstream   1~16

  • 1
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YieldReaction ConditionsOperation in experiment
72% at 20℃; for 4.5 h; Cooling with ice General procedure: A solution of di-tert-butyl dicarbonate (22 g, 100 mmol) inMeOH (20 mL) was added over 30 min to a stirred solutionof 1,4-diaminobutane (25, 1.8 g, 20 mmol) in MeOH (160 mL)under ice-cooling. After stirring for 4 h at room temperature,the solvent was removed under reduced pressure. The residuewas purified by silica gel column chromatography (CHCl3:MeOH: aq. NH3=10 : 1 : 0.1) to give the title compound (26)in 83percent yield.
51% at 0 - 20℃; for 12 h; [113] To a solution of 1,5-diaminopentane (15) (1.14 ml, 9.79 mmol) in dichloromethane (100 ml) was added di-tert-butyl dicarbonate (1.12 ml, 4.90 mmol) at 0 0C, and the resulting solution was stirred at room temperature for 12 hours. After the reaction was completed, H2O was added to remove solid residue. The reaction mixture was basified with IN NaOH aqueous solution to pH 10-11 and extracted with dichloromethane three times. Then, the combined organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to <n="14"/>silica gel column chromatography (eluent: dichloromethane:methnol: ammonia water = 100:9:1) to give the target compound as a yellow liquid (1.00 g, 51 percent).[114] 1H-NMR (400 MHz, CDCl3) δ 4.57 (br, IH, -NH-), 3.11-3.09 (d, J = 6.2 Hz, 2H, - NH-CH2-), 2.71-2.67 (t, J = 6.9 Hz, -CH2-(Bn)2), 1.78 (br, 2H, -NH2), 1.51-1.44 (m, 4H, -NH-CH2-CH2-, -Cu2- CH2- N-(Bn)2), 1.42 (s, 9H, -O(CH3)3), 1.37-1.31 (m, 2H, -CH2-CH2-CH2-).
20% With hydrogenchloride; sodium hydroxide In water; <i>tert</i>-butyl alcohol EXAMPLE 2
1,5-Diaminopentane (14.0 ml, 120 mmol) was dissolved in tert.-butanol (70 ml) and was treated dropwise over a period of 10 minutes with di-tert-butyl dicarbonate (9.2 ml, 40 mmol).
After the addition had been completed, the reaction mixture was stirred at room temperature for 16.5 hours.
The reaction mixture was then treated with 1N sodium hydroxide solution (aq) (90 ml), stirred for 1 hour and finally extracted with chloroform.
The chloroform extracts were dried (MgSO4) and concentrated under vacuum.
The residue was dissolved in water, made acidic (pH=2) by the dropwise addition of 3N hydrochloric acid at 0° and was washed with ether to remove the diprotected diamine.
The aqueous portion was made basic (pH 10) with 5percent sodium carbonate solution and was extracted with ethyl acetate to give 1.6 g (20percent) of mono-Boc-1,5-diaminopentane.
20% With hydrogenchloride; sodium hydroxide In water; <i>tert</i>-butyl alcohol EXAMPLE 9
Preparation of: STR13
1,5-Diaminopentane (14.0 ml, 120 mmol) was dissolved in tert.-butanol(70 ml) and was treated dropwise over a period of 10 min with di-tert-butyl dicarbonate (9.2 ml, 40 mmol).
After the addition had been completed, the reaction mixture was stirred at room temperature for 16.5 hr.
The reaction was then treated with lN sodium hydroxide solution (aq) (90 ml), stirred for 1 hr and finally extracted with chloroform.
The chloroform extracts were dried (MgSo4) and concentrated under vacuum.
The residue was dissolved in water, made acidic (pH=2) by the dropwise addition of 3N hydrochloric acid at 0° and was washed with ether to remove the diprotected diamine.
The aqueous portion was made basic (pH 10) with 5percent sodium carbonate solution and was extracted with ethyl acetate to give 1.6 g (20percent) of mono-Boc 1,5-diaminopentane.
The structure was confirmed by 'H NMR and CI-MS.
To a solution of the heptapeptide prepared in Example 8 and mono-Boc-1,5-diaminopentane in dimethylformamide, dicyclohexylcarbodiimide and 1-hydroxybenzotriazole hydrate is added.

Reference: [1] European Journal of Organic Chemistry, 1998, # 5, p. 853 - 859
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 6, p. 614 - 617
[3] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 20, p. 7145 - 7155
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 20, p. 4933 - 4940
[5] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 5, p. 326 - 333
[6] Organic and Biomolecular Chemistry, 2012, vol. 10, # 27, p. 5258 - 5265
[7] Journal of Medicinal Chemistry, 1997, vol. 40, # 16, p. 2643 - 2652
[8] Tetrahedron Letters, 1996, vol. 37, # 4, p. 551 - 554
[9] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 11, p. 3353 - 3358
[10] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 21, p. 5740 - 5743
[11] Patent: WO2008/136631, 2008, A1, . Location in patent: Page/Page column 5; 12-13
[12] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2005, vol. 60, # 1, p. 89 - 98
[13] Journal of Medicinal Chemistry, 1989, vol. 32, # 2, p. 391 - 396
[14] Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2175 - 2179
[15] European Journal of Medicinal Chemistry, 2004, vol. 39, # 11, p. 975 - 988
[16] Journal of Organic Chemistry, 2005, vol. 70, # 16, p. 6230 - 6241
[17] Patent: US4604378, 1986, A,
[18] Patent: US4826813, 1989, A,
[19] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4388 - 4391
[20] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 17, p. 6354 - 6359
[21] Chinese Chemical Letters, 2014, vol. 25, # 12, p. 1545 - 1549
[22] Patent: WO2014/202775, 2014, A1, . Location in patent: Sheet 14/33
[23] Chemical Biology and Drug Design, 2015, vol. 85, # 2, p. 145 - 152
[24] Bioorganic Chemistry, 2018, vol. 80, p. 649 - 654
  • 2
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  • [ 1476-39-7 ]
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YieldReaction ConditionsOperation in experiment
55% With triethylamine In 1,4-dioxane; water at 20℃; for 12 h; Inert atmosphere A solution of 2-(Boc-oxyimino)-2-phenylacetonitrile (226 mg, 0.92 mmol) in 1,4-dioxane (30 mL) was added via syringe pump (rate=8 mL/hr) to a stirred solution of 1,5 diaminopentane dihydrochloride (1 g, 5.52 mmol) and TEA (1 ml, 7.12 mmol) in 1:1 1,4-dioxane:water (40 mL) under inert atmosphere at room temperature. The reaction was stirred for 12 h and DCM (20 mL) was added to the reaction mixture. The organic phase was extracted and concentrated in vacuo. The yellow residue was dissolved in diethyl ether (15 mL) and 5percent HCl solution added. The acidic solution was washed with diethyl ether and then the pH of the aqueous layer adjusted to pH 14 with 2.5M NaOH solution. Ethyl acetate (20 mL) was added and the organic layer was washed with brine (2×50 mL), and dried (MgSO4). The solvents were evaporated in vacua to yield N-Boc-cadaverine as a yellow oil (100 mg, 55percent). HPLC/MS (Hydrophilic/TFA) Rt=6.17 min; ESI MS (+ve) m/z=203 [M+1H); calc. m/z for C10H22N2O2: 202.3 g/mol,
Reference: [1] Patent: US9127130, 2015, B2, . Location in patent: Page/Page column 47
  • 3
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Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
  • 4
  • [ 462-94-2 ]
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  • [ 34237-69-9 ]
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Reference: [1] Synthetic Communications, 1990, vol. 20, # 16, p. 2559 - 2564
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 16, p. 5457 - 5479
[3] Journal of Medicinal Chemistry, 1999, vol. 42, # 21, p. 4380 - 4387
[4] Organic Letters, 2015, vol. 17, # 3, p. 422 - 425
  • 5
  • [ 181780-37-0 ]
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Reference: [1] Journal of Chemical Research, Miniprint, 1996, # 8, p. 2143 - 2161
  • 6
  • [ 462-94-2 ]
  • [ 24424-99-5 ]
  • [ 51644-96-3 ]
YieldReaction ConditionsOperation in experiment
20% With hydrogenchloride; sodium hydroxide In water; <i>tert</i>-butyl alcohol EXAMPLE 2
1,5-Diaminopentane (14.0 ml, 120 mmol) was dissolved in tert.-butanol (70 ml) and was treated dropwise over a period of 10 min with di-tert-butyl dicarbonate (9.2 ml, 40 mmol).
After the addition had been completed, the reaction mixture was stirred at room temperature for 16.5 hr.
The reaction was then treated with 1N sodium hydroxide solution (aq) (90 ml), stirred for 1 hr and finally extracted with chloroform.
The chloroform extracts were dried (MgSO4) and concentrated under vacuum.
The residue was dissolved in water, made acidic (pH=2) by the dropwise addition of 3N hydrochloric acid at 0° and was washed with ether to remove the diprotected diamine.
The aqueous portion was made basic (pH 10) with 5percent sodium carbonate solution and was extracted with ethyl acetate to give 1.6 g (20percent) of mono-Boc 1,5-diaminopentane.
The structure was confirmed by 'H NMR and CI-MS.
To a solution of the D-Tyr2 -proline heptapeptide, prepared as described in Example 1, (29.7 mg, 0.0331 mmol) and mono-Boc-1,5-diaminopentane (20.2 mg, 0.0996 mmol) in dimethylformamide (400 μl), dicyclohexylcarbodiimide (10.3 mg, 0.05 mmol) and 1-hydroxybenzotriazole hydrate (6.7 mg, 0.05 mmol) were added.
The reaction mixture was stirred at room temperature for 19 hours.
The dimethylformamide was, then, removed under vacuum.
The residue was treated with trifluoroacetic acid at 0° for 2 hours.
After this time, the trifluoroacetic acid was removed under vacuum and the residue in 1percent acetic acid was passed over a BioRex 70 (H+) ion exchange column.
The basic products were washed off the ion exchange column with pyridine buffer (H2 O/pyridine/HOAc, 66:30:4) and evaporated.
Final purification by prep HPLC (5μ Ultrasphere ODS) gave 5.4 mg (17percent) of pure [1-(β-mercapto-β,β-cyclopentamethylenepropionic acid)-2-D-tyrosine-4-valine-8-(1,5-diaminopentane)-8-desarginine- 9-desglycinamide]-vasopressin.
Reference: [1] Patent: US4543349, 1985, A,
  • 7
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Reference: [1] Medicinal Chemistry letters, 2012, vol. 3, # 8, p. 640 - 644,5
[2] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 8, p. 640 - 644
[3] Synthesis, 2002, # 15, p. 2195 - 2202
[4] Organic Syntheses, 2007, vol. 84, p. 209 - 214
  • 8
  • [ 462-94-2 ]
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Reference: [1] European Journal of Organic Chemistry, 2001, # 13, p. 2535 - 2545
[2] Journal of Medicinal Chemistry, 1989, vol. 32, # 1, p. 79 - 84
  • 9
  • [ 129392-86-5 ]
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Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 36, p. 6479 - 6482
[2] Tetrahedron Letters, 1997, vol. 38, # 48, p. 8297 - 8298
  • 10
  • [ 24424-99-5 ]
  • [ 51644-96-3 ]
Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
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Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
  • 12
  • [ 91419-47-5 ]
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Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
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Reference: [1] Synthesis, 1988, # 3, p. 259 - 261
  • 14
  • [ 75178-90-4 ]
  • [ 51644-96-3 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1996, # 8, p. 2143 - 2161
  • 15
  • [ 181780-36-9 ]
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Reference: [1] Journal of Chemical Research, Miniprint, 1996, # 8, p. 2143 - 2161
  • 16
  • [ 462-94-2 ]
  • [ 1538-75-6 ]
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Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 9, p. 4457 - 4478
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