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[ CAS No. 5349-24-6 ] {[proInfo.proName]}

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Chemical Structure| 5349-24-6
Chemical Structure| 5349-24-6
Structure of 5349-24-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5349-24-6 ]

CAS No. :5349-24-6 MDL No. :MFCD00776256
Formula : C6H12ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :XBTFKFOPYRYZDH-UHFFFAOYSA-N
M.W : 149.62 Pubchem ID :219645
Synonyms :

Calculated chemistry of [ 5349-24-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 5
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.75
TPSA : 29.1 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) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 1.41
Log Po/w (WLOGP) : 1.14
Log Po/w (MLOGP) : 1.22
Log Po/w (SILICOS-IT) : 1.38
Consensus Log Po/w : 1.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.33
Solubility : 7.06 mg/ml ; 0.0472 mol/l
Class : Very soluble
Log S (Ali) : -1.63
Solubility : 3.54 mg/ml ; 0.0237 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.48
Solubility : 0.491 mg/ml ; 0.00328 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 5349-24-6 ]

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

Application In Synthesis of [ 5349-24-6 ]

* 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 [ 5349-24-6 ]
  • Downstream synthetic route of [ 5349-24-6 ]

[ 5349-24-6 ] Synthesis Path-Upstream   1~8

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  • [ 79-04-9 ]
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YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide In dichloromethane; water at 20℃; for 2 h; Cooling with ice Chloroacetyl chloride (0.2 mol, 15.9mL)(CAS: 79-04-9) in an ice bath was slowly added dropwise to moderate molar amount of n- butylamine (0.2mol,14.83g) in dichloromethane (50 mL) and 20percent (mass percentage) of Aqueous NaOH as solvent, after the addition was complete, warmed to room temperature stirring was continued for 2h. Collect the organic phase,And a 5percent (mass percentage) of HCl and 5percent (mass percentage) NaHCO 3 and washed (3 × 25 mL of) theorganic phase was dried and filtered, and the solvent removed under reduced pressure to give the intermediatechloroacetyl -n- butylamine (Yield92percent). The intermediate product (0.05mol, 9.00g) and 5,6,7,8-tetrahydropyrido[1,2-α] Imidazole (0.05mol, 6.11g) (CAS: 34167-66-3) mixed in acetonitrile (50 mL), and Was added the reaction was refluxed for 18H, after the reaction with acetonitrile and recrystallized from ethyl acetateoperation, the product was collected Was [4C-imCH 2 CONHBu] Cl (yield89percent), after anion exchange resinobtained by [4C-imCH 2 CONHBu] OH.
86% With potassium carbonate In dichloromethane at 0℃; for 2 h; EXAMPLE 30; N-Butyl-2-chloro-acetamide; [0241] An argon-flushed vial was charged with 10 mL of DCM and chloroacetyl chloride (5.5 mmol, 621 mg). The solution was cooled to 0 °C and n-butylamine (5.0 mmol, 366 mg) was slowly added. Then K2CO3 (5.5 mmol, 760 mg) was added and the mixture was agitated for 2h. The reaction mixture was filtered and concentrated in vacuo. Yield: 584 mg (86percent). 1H NMR (400 MHz, CDCl3) δ 6.60 (s, IH), 4.00 (s, 2H), 3.32-3.22 (m, 2H), 1.56- 1.44 (m, 2H), 1.40-1.16 (m, 4H)5 0.91 (t, J=7.3, 3H), 0.89 (t, J=6.6, 3H). (100 MHz, CDCl3) δ: 165.8, 42.8, 39.7, 31.5, 20.1, 13.7.
Reference: [1] Patent: CN104326949, 2016, B, . Location in patent: Paragraph 0060; 0061; 0063
[2] Patent: WO2007/9083, 2007, A2, . Location in patent: Page/Page column 68
[3] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 6, p. 678 - 681
[4] ChemMedChem, 2018,
[5] Organic Letters, 2004, vol. 6, # 26, p. 4805 - 4808
[6] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7590 - 7599
[7] Journal of the American Chemical Society, 1956, vol. 78, p. 2556,2557
[8] Archiv der Pharmazie (Weinheim, Germany), 2002, vol. 335, # 1, p. 15 - 21
[9] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 204 - 206
[10] Green Chemistry, 2012, vol. 14, # 6, p. 1721 - 1727
[11] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 6, p. 1479 - 1483
[12] Chemical Biology and Drug Design, 2014, vol. 84, # 6, p. 685 - 696
[13] RSC Advances, 2015, vol. 5, # 60, p. 48368 - 48381
[14] Patent: CN106167497, 2016, A, . Location in patent: Paragraph 0125; 0126
[15] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 527 - 532
[16] Patent: CN106543099, 2017, A, . Location in patent: Paragraph 0038
[17] Patent: CN106146414, 2016, A, . Location in patent: Paragraph 0150; 0151; 0152
[18] Bulletin of the Korean Chemical Society, 2018, vol. 39, # 2, p. 146 - 155
[19] Patent: CN107556210, 2018, A, . Location in patent: Paragraph 0041; 0042
[20] Molecules, 2018, vol. 23, # 5,
  • 2
  • [ 638-07-3 ]
  • [ 109-73-9 ]
  • [ 5349-24-6 ]
YieldReaction ConditionsOperation in experiment
99% With 4-toluenesulfonyl azide In tetrahydrofuran at 20 - 25℃; General procedure: To a solution of the corresponding β-keto ester 1 (1.0 mmol) and TsN3 (197 mg, 1.0 mmol) in THF (2.0 mL) under stirring at 25 °C was added the amine (1.1 mmol). Then the reaction mixture was stirred at room temperature until consumption of the starting material (monitored by TLC: 30 min to 29 h, see Table 1 and Scheme 4). Next, the mixture was diluted in 5 mL of CH2Cl2 and concentrated under reduced pressure. After complete removal of the solvent, the residue was triturated in ethyl ether and the resulting mixture was again concentrated under reduced pressure. The final solid residue was repeatedly triturated with hexane (for amides 3 and 4) or a 9:1 hexane/CH2Cl2 mixture (for amides 5 and 6) to separate out the insoluble TsNH2 by decantation. The resulting supernatants were filtered and concentrated under reduced pressure to give the known amides25 3-6 as oils with high degree of purity. Alternatively, further purification through column chromatography on silica gel using gradient mixtures of hexane/EtOAc as eluent was employed to furnish pure products in 80-99percent yield.
Reference: [1] Tetrahedron, 2017, vol. 73, # 31, p. 4549 - 4559
  • 3
  • [ 227945-00-8 ]
  • [ 5349-24-6 ]
Reference: [1] Patent: US6121322, 2000, A,
  • 4
  • [ 109-73-9 ]
  • [ 5349-24-6 ]
Reference: [1] Tetrahedron, 2017, vol. 73, # 31, p. 4549 - 4559
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  • [ 7572-29-4 ]
  • [ 109-73-9 ]
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  • [ 101432-82-0 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1995, vol. 104, # 6, p. 407 - 410
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Reference: [1] Bulletin des Societes Chimiques Belges, 1995, vol. 104, # 6, p. 407 - 410
  • 7
  • [ 38766-10-8 ]
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  • [ 5349-24-6 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 16, p. 2155 - 2164
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  • [ 7572-29-4 ]
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  • [ 101432-82-0 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1995, vol. 104, # 6, p. 407 - 410
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