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[ CAS No. 6160-65-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 6160-65-2
Chemical Structure| 6160-65-2
Chemical Structure| 6160-65-2
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Product Details of [ 6160-65-2 ]

CAS No. :6160-65-2 MDL No. :MFCD00005289
Formula : C7H6N4S Boiling Point : -
Linear Structure Formula :- InChI Key :RAFNCPHFRHZCPS-UHFFFAOYSA-N
M.W :178.21 Pubchem ID :80264
Synonyms :

Calculated chemistry of [ 6160-65-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.85
TPSA : 67.73 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.17
Log Po/w (XLOGP3) : 0.68
Log Po/w (WLOGP) : 0.76
Log Po/w (MLOGP) : -0.42
Log Po/w (SILICOS-IT) : 0.88
Consensus Log Po/w : 0.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.86
Solubility : 2.47 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (Ali) : -1.68
Solubility : 3.73 mg/ml ; 0.0209 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.09
Solubility : 14.5 mg/ml ; 0.0815 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.27

Safety of [ 6160-65-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P280-P301+P312+P330-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362+P364-P501 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6160-65-2 ]

* 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 [ 6160-65-2 ]
  • Downstream synthetic route of [ 6160-65-2 ]

[ 6160-65-2 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 463-71-8 ]
  • [ 18156-74-6 ]
  • [ 6160-65-2 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1992, vol. 26, # 3, p. 259 - 262[2] Khimiko-Farmatsevticheskii Zhurnal, 1992, vol. 26, # 3, p. 59 - 62
[3] Journal of the American Chemical Society, 1995, vol. 117, # 34, p. 8757 - 8768
  • 2
  • [ 288-32-4 ]
  • [ 463-71-8 ]
  • [ 6160-65-2 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 3, p. 764 - 766
  • 3
  • [ 6160-65-2 ]
  • [ 1575-37-7 ]
  • [ 68468-39-3 ]
Reference: [1] Patent: WO2008/55959, 2008, A1, . Location in patent: Page/Page column 68
  • 4
  • [ 5348-42-5 ]
  • [ 6160-65-2 ]
  • [ 19462-98-7 ]
Reference: [1] Archiv der Pharmazie, 2000, vol. 333, # 5, p. 123 - 129
  • 5
  • [ 1072-97-5 ]
  • [ 39590-27-7 ]
  • [ 6160-65-2 ]
  • [ 613-69-4 ]
Reference: [1] Patent: US5593993, 1997, A,
  • 6
  • [ 6101-31-1 ]
  • [ 6160-65-2 ]
  • [ 51908-29-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 4, p. 918 - 927
  • 7
  • [ 2243-47-2 ]
  • [ 6160-65-2 ]
  • [ 1510-25-4 ]
YieldReaction ConditionsOperation in experiment
96% With dmap In dichloromethane at 20℃; for 1 h; Inert atmosphere To a stirred solution of biphenyl-3-ylamine (338 mg, 2 mmol) in DCM (5 mL), thiocarbonyldiimidazole (TCDI) (535 mg, 3 mmol) and DMAP (48.8 mg, 0.04 mmol) were added and the reaction mixture stirred at r.t under N2 for 1 h (until TLC showed no starting material remaining). The reaction mixture was then purified by a silica plug (DCM). The solvent was then removed in vacuo to leave a colourless oil (407 mg, 96percent). Rf: 0.86 (1:1 DCM/hex). 1H NMR (CDCl3): δ 7.16 (ddd, 1H, J 8, 2, 1 Hz, H6'), 7.34-7.48 (m, 6H, H4'', H5', H4', H3'', H5'', H2'), 7.52 (m, 2H, H2'', H6''). 13C NMR (CDCl3): δ 124.4 (CH), 124.5 (CH), 126.2 (CH), 127.2 (CH), 128.2 (CH), 129.1 (CH), 130.0 (CH), 131.8 (C), 135.7 (NCS), 139.5 (C), 143.0 (C).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 22, p. 6782 - 6787
  • 8
  • [ 6160-65-2 ]
  • [ 57260-71-6 ]
  • [ 196811-66-2 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: at 20 - 50℃; for 3 h;
Stage #2: With ammonia In tetrahydrofuran; methanol at 0 - 60℃; for 20 h;
To a solution of 1-boc piperazine (5.0 g, 26.88 mmol) in dry THF (50 mL), 1,1-thiocarbonylimidazole (5.48 g, 29.56 mmol) was added at room temperature and stirred for 2 h. The reaction mixture was heated at 50°C for 1 h. It was cooled down to 0 °C and methanolic ammonia solution (50 mL, 7 N) was added. The mixture was stirred at 60°C for 20 h. It was then diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by flash chromatography to give the title compound. Yield: 92percent (4.0 g, white solid). 1H NMR (400 MHz, DMSO-d6): δ 9.2 (m, 2H), 3.16-3.14 (m, 2H), 2.49-2.48 (m, 6H), 1.30 (s, 9H). LCMS: (Method A) 246.2 (M+H), Rt. 2.93 min, 95.3percent (Max).
92%
Stage #1: at 20 - 50℃; for 2 h;
Stage #2: With ammonia In tetrahydrofuran; methanol at 0 - 60℃; for 20 h;
To a solution of 1-boc piperazine (5.0 g, 26.88 mmol) in dry THE (50 mL), 1,1-thio carbonylimidazole (5.48 g, 29.56 mmol) was added at room temperature and stirred for 2 h. The reaction mixture was heated at 50°C for I h. It was cooled down to 0 °C and methanolic ammonia solution (50 mL, 7 N) was added. The mixture was stirred at 60°C for 20 h. It was then diluted with water and extracted with EtOAc. The organic layerwas dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by flash chromatography to give the title compound. Yield: 92percent (4.0 g, white solid). 1H NMR (400 MHz, DMSO-d6): 6 9.2 (m, 2H), 3.16-3.14 (m, 2H), 2.49-2.48 (m, 6H), 1.30 (s, 9H). LCMS: (Method A) 246.2 (M+H), Rt. 2.93 mm, 95.3percent (Max).
72%
Stage #1: at 20℃; for 1 h;
Stage #2: With ammonia In tetrahydrofuran; water at 20℃; for 12 h;
The production of compound No. 26 proceeds according to the sequence of reaction steps shown in the following schemes: The first sub-step shown above was performed at 20° C. during 2 hours with a molar excess of CH2N2 (about 2 molar equivalents) in dry ether, then in a second sub-step (shown below) performed at 5° C. HCl gas was bubbled into the reaction mixture for 15 minutes, and the desired intermediate was obtained in 71percent yield. For the conversion from 3 to 4, the first sub-step shown above was performed at 20° C. during 1 hour with a molar excess of thio-carbonyldiimidazole (about 2 molar equivalents) in THF, then in a second sub-step performed at 20° C. for 12 hours a 25percent aqueous NH3 solution was added, and the desired intermediate was obtained in 72percent yield. The conversion from 4 to 5 was performed during 6 hours with 1 molar equivalent NaHCO3 at reflux in methanol, and the desired intermediate was obtained in 92percent yield. The conversion from 5 to 6 was performed during 3 hours at 20° C., and the desired intermediate was obtained in 90percent yield. The conversion from 6 to the final compound was performed during 6 hours at 20° C. in 1,2-dichloroethane (DCE) in the presence of a molar excess of triethylamine (1.2 molar equivalents).
69%
Stage #1: at 20 - 55℃; for 3 h;
Stage #2: With ammonia In tetrahydrofuran; methanol at 20℃; for 72 h;
To a solution of di(lH-imidazol-l- yl)methanethione 2 (2.14 g, 12 mmol) in anhydrous THF (30 mL) was added tert-butyl piperazine-l-carboxylate 1 (1.86 g, 10 mmol) at ambient temperature. The mixture was allowed to stir at ambient temperature for 2 h, then the mixture was heated at 55 °C for 1 h. The mixture was concentrated under vacuum to about half the volume. To the remaining reaction mixture was added 2 M solution of ammonia in methanol (20 mL) and allowed to stir at ambient temperature for 3 days. The solvent was removed and the residue was purified by chromatography eluting with 50: 1 DCM/MeOH to afford the title compound (1.7 g, 69percent) as white solid. MS (ESI): m/z = 246.1 [M + H]+.

Reference: [1] Patent: WO2016/30443, 2016, A1, . Location in patent: Page/Page column 106
[2] Patent: WO2017/144637, 2017, A1, . Location in patent: Page/Page column 39
[3] Patent: US2010/197703, 2010, A1, . Location in patent: Page/Page column 77
[4] Patent: WO2015/48662, 2015, A2, . Location in patent: Page/Page column 105
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1613 - 1631
[6] Journal of Medicinal Chemistry, 1998, vol. 41, # 25, p. 5037 - 5054
[7] Patent: WO2004/41815, 2004, A1, . Location in patent: Page/Page column 25-26
[8] Patent: WO2006/72436, 2006, A1, . Location in patent: Page/Page column 65; 71; 78; 80
[9] Patent: WO2011/72207, 2011, A1, . Location in patent: Page/Page column 49
  • 9
  • [ 1484-26-0 ]
  • [ 6160-65-2 ]
  • [ 206559-36-6 ]
Reference: [1] Patent: WO2005/7601, 2005, A2, . Location in patent: Page/Page column 35-36
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