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[ CAS No. 4403-69-4 ] {[proInfo.proName]}

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Chemical Structure| 4403-69-4
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Product Details of [ 4403-69-4 ]

CAS No. :4403-69-4 MDL No. :MFCD00075408
Formula : C7H10N2 Boiling Point : -
Linear Structure Formula :H2NC6H4CH2NH2 InChI Key :GVOYKJPMUUJXBS-UHFFFAOYSA-N
M.W : 122.17 Pubchem ID :178096
Synonyms :

Calculated chemistry of [ 4403-69-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 38.52
TPSA : 52.04 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.1
Log Po/w (XLOGP3) : -0.31
Log Po/w (WLOGP) : 0.58
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : 0.74
Consensus Log Po/w : 0.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.83
Solubility : 18.1 mg/ml ; 0.148 mol/l
Class : Very soluble
Log S (Ali) : -0.32
Solubility : 58.2 mg/ml ; 0.476 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.04
Solubility : 1.12 mg/ml ; 0.00918 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 4403-69-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501 UN#:3259
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4403-69-4 ]

* 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 [ 4403-69-4 ]
  • Downstream synthetic route of [ 4403-69-4 ]

[ 4403-69-4 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 50-00-0 ]
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  • [ 253-82-7 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 33, p. 4628 - 4638
[2] Advanced Synthesis and Catalysis, 2012, vol. 354, # 16, p. 2899 - 2904
  • 2
  • [ 67-56-1 ]
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  • [ 253-82-7 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 44, p. 9205 - 9207
  • 3
  • [ 144-62-7 ]
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  • [ 253-82-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1337 - 1342
  • 4
  • [ 4403-69-4 ]
  • [ 13939-06-5 ]
  • [ 66655-67-2 ]
YieldReaction ConditionsOperation in experiment
12% With copper diacetate; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 95℃; General procedure: The reaction was performed in a double-chamber system [67,68]. Amine/amines, Pd(OAc)2(0.05 equiv.) and Cu(OAc)2 (0.5 equiv.) were added to the reaction chamber and dissolved in1,4-dioxane (2 mL). In the CO-chamber was Mo(CO)6 (200 mg) dissolved in 1,4-dioxane (2 mL).After capping of the system, 1,8-diazabicyclo[5.4.0]undec-7-ene was added to the CO-chamber.The double-chamber system was positioned in a Dry–Syn heating block and heated to 95 C. Aftercompletion of the reaction, the reaction mixture was filtered through a short silica plug before flashcolumn chromatography.
Reference: [1] Molecules, 2017, vol. 22, # 10,
  • 5
  • [ 201230-82-2 ]
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  • [ 66655-67-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, p. 1793 - 1800
[2] European Journal of Organic Chemistry, 2011, # 31, p. 6261 - 6268
[3] Journal of Organic Chemistry, 2000, vol. 65, # 17, p. 5216 - 5222
[4] Tetrahedron Letters, 1986, vol. 27, # 26, p. 3037 - 3040
[5] Phosphorus and Sulfur and the Related Elements, 1988, vol. 38, p. 137 - 148
[6] Phosphorus and Sulfur and the Related Elements, 1988, vol. 38, p. 137 - 148
  • 6
  • [ 32315-10-9 ]
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  • [ 66655-67-2 ]
YieldReaction ConditionsOperation in experiment
99% Inert atmosphere Triphosgene (3.31 g, 12.3 mmol) was added toa solution of 2-(aminomethyl)aniline (1.50 g, 12.3 mmol) in 30 ml THF under a nitrogenatmosphere. After precipitation of a colorless solid, stirring was continued for 30 minbefore water was added. The solution was extracted several times with ethyl acetate. Thecombined organic layers were washed with brine and dried over anhydrous MgSO4 toafford 10b (1.80 g, 12.2 mmol, 99 percent) as colorless solid. 1H-NMR (500 MHz, DMSO-d6):δ = 4.30 (s, 2H), 6.75-6.77 (m, 2H), 6.84 (ddd, 3J = 3J = 7.4 Hz, 4J = 1.9 Hz, 1H), 7.06 (d,3J = 7.3 Hz, 1H), 7.09 (dd, 3J = 3J = 7.7 Hz, 1H), 8.98 (s, 1H). 13C-NMR (125 MHz,DMSO-d6): δ = 42.4, 113.4, 118.0, 120.8, 125.5, 127.4, 138.0, 154.5.
Reference: [1] European Journal of Medicinal Chemistry, 2014, vol. 90, p. 788 - 796
  • 7
  • [ 103-71-9 ]
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Reference: [1] Science China Chemistry, 2014, vol. 57, # 8, p. 1117 - 1125
  • 8
  • [ 124-38-9 ]
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  • [ 66655-67-2 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 9, p. 3037 - 3046
  • 9
  • [ 24424-99-5 ]
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  • [ 66655-67-2 ]
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 17, p. 1614 - 1618
  • 10
  • [ 4403-69-4 ]
  • [ 105-58-8 ]
  • [ 66655-67-2 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 8, p. 1517 - 1520
  • 11
  • [ 868-84-8 ]
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  • [ 66655-67-2 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 12, p. 4175 - 4179
  • 12
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  • [ 66655-67-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 656 - 658
  • 13
  • [ 75-44-5 ]
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  • [ 66655-67-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1895, vol. <2> 51, p. 126
  • 14
  • [ 556-18-3 ]
  • [ 4403-69-4 ]
  • [ 2963-77-1 ]
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 11, p. 1046 - 1049
  • 15
  • [ 68-12-2 ]
  • [ 4403-69-4 ]
  • [ 6526-66-5 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 24, p. 15268 - 15276
  • 16
  • [ 4403-69-4 ]
  • [ 79098-75-2 ]
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 36, p. 3389 - 3391
  • 17
  • [ 24424-99-5 ]
  • [ 4403-69-4 ]
  • [ 849020-94-6 ]
YieldReaction ConditionsOperation in experiment
88% at 20℃; Example 1
3-Methyl-but-2-enoic acid (2-aminomethyl-phenyl)-amide
To a solution of 2-aminobenzylamine (2.440 g, 20.0 mmol) in dry dichloromethane (30 mL) was added a solution of di-tert-butyl dicarbonate (4.360 g, 20.0 mmol) in dry dichloromethane (12 mL) dropwise at room temperature over a few minutes.
The reaction was then allowed to proceed until it was deemed complete by TLC (ethyl acetate:hexane 1:1, 30 min.).
The volatiles were removed and the resulting solid was purified by flash column chromatography using ethyl acetate-hexanes (1.5:8.5 to 3:7), affording 3.912 g of N-(-tert-butoxycarbonyl)-2-aminobenzylamine as an off-white powder (88percent), which gave satisfactory spectroscopic and analytical data.
Reference: [1] Patent: US6927294, 2005, B1, . Location in patent: Page/Page column 18
  • 18
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  • [ 162046-50-6 ]
YieldReaction ConditionsOperation in experiment
96.2% at 20℃; Inert atmosphere; Cooling with ice Take 2-amino-benzylamine (6.0g, 49.2mmol) was dissolved in methylene chloride, N2Protection, under ice-bath stirred and added dropwise (Boc)2O (10.7g, 49.2mmol) in methylene chloride.Bi drops warmed to room temperature and stirred overnight.Thin layer chromatography until the reaction was complete.After completion of the reaction, successively with distilled water, the reaction solution was washed with saturated saline.Dried over anhydrous sodium sulfate, suction filtered, the solvent was distilled off under reduced pressure.Have intermediate 5, 10.5g, a yield of 96.2percent.
79.7% at 20℃; for 4 h; To a solution of 2-(aminomethyl)aniline (10.00 g, 81.85 mmol) in ACN (100 mL) was added Boc20 (17.86 g, 81.85 mmol) in portions. The mixture was stirred at room temperature for 4 h, after which TLC showed the reaction was complete. The mixture was concentrated in vacuo, and the residue was washed with PE/MTBE (50/1), filtered, and filter cake was concentrated in vacuo to afford tert-butyl 2-aminobenzylcarbamate (14.50 g, 79.7percent) as a white solid. 1H NMR: (DMSO; 400MHz) δ 7.27-7.24 (m, 1H), 6.97-6.94 (m, 2H), 6.63 (d, J = 8.00 Hz, 1H), 6.53-6.49 (m, 1H), 5.01 (s, 2H), 3.99 (d, J = 6.00 Hz, 2H), 1.41 (s, 9H). LCMS: (M+H+): 223.
20% With triethylamine In tetrahydrofuran at 20℃; for 16 h; Step a: Preparation of tert-butyl 2-aminobenzylcarbamate (11). To a THF (30 mL) solution of 2-aminobenzyl amine (2.0 g, 16.4 mmol) was added triethylamine (4.60 mL, 32.7 mmol) and di-tert-butyldicarbonate (4.3 g, 19.6 mmol). The reaction mixture was stirred at room temperature for 16 h. The crude reaction mixture was then poured over saturated aqueous NaHCψ3 and the product was then extracted with ethyl acetate. The organic phase was washed with brine and then dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-5percent methanol/dichloromethane) yielding 730 mg (20percent) of 11: 1H NMR (400 MHz, CDCl3) δ 7.12-7.80, (m, IH), 7.00 (d, J = 7.6 Hz, IH), 6.69-6.62 (m, 2H), 4.77, (bs, IH), 4.29-4.11, (m, 4H), 1.43(s, 9H); ESI+ MS: m/z (rel intensity) 223 (80, M+H).
Reference: [1] Patent: CN104016944, 2016, B, . Location in patent: Paragraph 0014-0015; 0046-0047
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 7, p. 1885 - 1889[3] Angew. Chem., 2017, vol. 129, # 7, p. 1911 - 1915,5
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 656 - 658
[5] Journal of Medicinal Chemistry, 2003, vol. 46, # 9, p. 1661 - 1669
[6] Patent: US2003/119751, 2003, A1,
[7] Patent: WO2015/154022, 2015, A1, . Location in patent: Paragraph 178-179
[8] Patent: US5767118, 1998, A,
[9] Patent: WO2009/121063, 2009, A2, . Location in patent: Page/Page column 148; 149
[10] Organic Letters, 2002, vol. 4, # 1, p. 63 - 66
[11] Patent: EP1591120, 2005, A1, . Location in patent: Page/Page column 106
[12] Patent: EP2361902, 2011, A1, . Location in patent: Page/Page column 37
[13] Inorganic Chemistry, 2015, vol. 54, # 12, p. 5949 - 5959
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Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 9, p. 4588 - 4603
  • 20
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  • [ 1246765-38-7 ]
Reference: [1] European Journal of Medicinal Chemistry, 2014, vol. 90, p. 788 - 796
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