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[ CAS No. 51779-32-9 ] {[proInfo.proName]}

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Chemical Structure| 51779-32-9
Chemical Structure| 51779-32-9
Structure of 51779-32-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 51779-32-9 ]

CAS No. :51779-32-9 MDL No. :MFCD00043309
Formula : C10H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :XCAQIUOFDMREBA-UHFFFAOYSA-N
M.W : 217.26 Pubchem ID :279800
Synonyms :

Calculated chemistry of [ 51779-32-9 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.41
TPSA : 64.63 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) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.6
Log Po/w (XLOGP3) : 2.1
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 1.13
Log Po/w (SILICOS-IT) : 0.65
Consensus Log Po/w : 1.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.11
Solubility : 1.67 mg/ml ; 0.00769 mol/l
Class : Soluble
Log S (Ali) : -3.09
Solubility : 0.178 mg/ml ; 0.000817 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.74
Solubility : 3.97 mg/ml ; 0.0183 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.1

Safety of [ 51779-32-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51779-32-9 ]

* 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 [ 51779-32-9 ]
  • Downstream synthetic route of [ 51779-32-9 ]

[ 51779-32-9 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 24424-99-5 ]
  • [ 51779-32-9 ]
Reference: [1] Acta Chemica Scandinavica, 1993, vol. 47, # 9, p. 896 - 898
  • 2
  • [ 78476-42-3 ]
  • [ 75-65-0 ]
  • [ 51779-32-9 ]
Reference: [1] Chemische Berichte, 1981, vol. 114, # 6, p. 2064 - 2074
  • 3
  • [ 1070-19-5 ]
  • [ 51779-32-9 ]
Reference: [1] Journal of Organic Chemistry, 1974, vol. 39, p. 2513 - 2516
  • 4
  • [ 50624-94-7 ]
  • [ 51779-32-9 ]
Reference: [1] Journal of Organic Chemistry, 1964, vol. 29, p. 2820 - 2824
  • 5
  • [ 89004-82-0 ]
  • [ 89004-80-8 ]
  • [ 51779-32-9 ]
  • [ 89004-83-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 12, p. 2983 - 2986
  • 6
  • [ 24424-99-5 ]
  • [ 77287-34-4 ]
  • [ 51779-32-9 ]
Reference: [1] Synthesis, 1987, # 3, p. 275 - 276
  • 7
  • [ 92819-78-8 ]
  • [ 75-65-0 ]
  • [ 51779-32-9 ]
Reference: [1] Journal of Organic Chemistry, 1964, vol. 29, p. 2820 - 2824
  • 8
  • [ 35454-04-7 ]
  • [ 75-65-0 ]
  • [ 51779-32-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1978, p. 1088 - 1090
  • 9
  • [ 51779-32-9 ]
  • [ 123-30-8 ]
  • [ 54840-15-2 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 11, p. 2789 - 2792
  • 10
  • [ 51779-32-9 ]
  • [ 17201-43-3 ]
  • [ 66389-80-8 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide In tetrahydrofuran; methanol; water B)
Preparation of N-Boc-p-(aminomethyl)benzonitrile.
To a stirring suspension of sodium hydride (4.6 g, 115 mmol, 60percent dispersion in oil) in tetrahydrofuran (150 mL) was added 4-(bromomethyl)benzonitrile (20.5 g, 105 mmol).
To this mixture was added (slowly via an addition funnel) a solution of di-t-butyl iminodicarboxylate (25 g, 115 mmol).
After stirring for 16 hours, the mixture was diluted with diethyl ether (500 mL) and washed twice with water (250 mL).
The organic phase was then dried (MgSO4), filtered and concentrated to give 40.2 g of crude solid.
The resulting solid (28.3 g, 85 mmol) was then dissolved in tetrahydrofuran (150 mL) and a solution of sodium hydroxide (3.4 g, 85 mmol) in methanol (300 mL) was added.
After stirring overnight, the solution was concentrated to about one-half volume and water was added to promote precipitation of the product.
The precipitate was filtered and dried in vacuo to give 18.5 g (94percent) of a white solid.
94% With sodium hydroxide In tetrahydrofuran; methanol; water B)
Preparation of N-Boc-p-(aminomethyl)benzonitrile
To a stirring suspension of sodium hydride (4.6 g, 115 mmol, 60percent dispersion in oil) in tetrahydrofuran (150 mL) was added 4-(bromomethyl)benzonitrile (20.5 g, 105 mmol).
To this mixture was added (slowly via an addition funnel) a solution of di-t-butyl iminodicarboxylate (25 g, 115 mmol).
After stirring for 16 hours, the mixture was diluted with diethyl ether (500 mL) and washed twice with water (250 mL).
The organic phase was then dried (MgSO4), filtered and concentrated to give 40.2 g of crude solid.
The resulting solid (28.3 g, 85 mmol) was then dissolved in tetrahydrofuran (150 mL) and a solution of sodium hydroxide (3.4 g, 85 mmol) in methanol (300 mL) was added.
After stirring overnight, the solution was concentrated to about one-half volume and water was added to promote precipitation of the product.
The precipitate was filtered and dried in vacuo to give 18.5 g (94percent) of a white solid.
94% With sodium hydroxide In tetrahydrofuran; methanol; water B)
Preparation of N-Boc-p-(aminomethyl)benzonitrile
To a stirring suspension of sodium hydride (4.6 g, 115 mmol, 60percent dispersion in oil) in tetrahydrofuran (150 mL) was added 4-(bromomethyl)benzonitrile (20.5 g, 105 mmol).
To this mixture was added (slowly via an addition funnel) a solution of di-t-butyl iminodicarboxylate (25 g, 115 mmol).
After stirring for 16 hours, the mixture was diluted with diethyl ether (500 mL) and washed twice with water (250 mL).
The organic phase was then dried (MgSO4), filtered and concentrated to give 40.2 g of crude solid.
The resulting solid (28.3 g, 85 mmol) was then dissolved in tetrahydrofuran (150 mL) and a solution of sodium hydroxide (3.4 g, 85 mmol) in methanol (300 mL) was added.
After stirring overnight, the solution was concentrated to about one-half volume and water was added to promote precipitation of the product.
The precipitate was filtered and dried in vacuo to give 18.5 g (94percent) of a white solid.
Reference: [1] Patent: US5705487, 1998, A,
[2] Patent: US5710130, 1998, A,
[3] Patent: US5726159, 1998, A,
[4] Patent: US5914319, 1999, A,
[5] Patent: US5707966, 1998, A,
  • 11
  • [ 51779-32-9 ]
  • [ 66389-80-8 ]
Reference: [1] Synthetic Communications, 1998, vol. 28, # 23, p. 4419 - 4429
  • 12
  • [ 51779-32-9 ]
  • [ 7101-51-1 ]
  • [ 37169-36-1 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 7, p. 1702 - 1705
  • 13
  • [ 51779-32-9 ]
  • [ 31719-77-4 ]
  • [ 876-03-9 ]
Reference: [1] Patent: US2003/109547, 2003, A1,
  • 14
  • [ 51779-32-9 ]
  • [ 85363-04-8 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 26, p. 9152 - 9156
  • 15
  • [ 51779-32-9 ]
  • [ 94838-58-1 ]
Reference: [1] Polish Journal of Chemistry, 2004, vol. 78, # 8, p. 1067 - 1072
  • 16
  • [ 51779-32-9 ]
  • [ 151978-58-4 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 7, p. 1754 - 1757
  • 17
  • [ 51779-32-9 ]
  • [ 95-55-6 ]
  • [ 186663-74-1 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 11, p. 2789 - 2792
  • 18
  • [ 51779-32-9 ]
  • [ 156731-40-7 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 30, p. 7271 - 7276
  • 19
  • [ 51779-32-9 ]
  • [ 1215071-17-2 ]
YieldReaction ConditionsOperation in experiment
8.3 g With triethylamine In dichloromethane at 20℃; for 16 h; A mixture of 3,3-difluoro-1-(4-methoxy benzyl)piperidin-4-one (10 g, 39.17 mmol) in 1,2-dichloroethane (100 mL) was added to 1-chloroethylchloroformate (16.86 g, 117.52 mmol) in three portion at a period of 30 min and it was reflux for 2 h. After completion of the reaction (TLC), the mixture was cooled to room temperature and then it was concentrated in vacuo to give as a yellow liquid. The yellow liquid was dissolved in methanol (100 mL) and it was reflux for 3 h. The completion of the reaction was monitored by TLC and then the cooled mixture was concentrated in vacuo to give as a brown liquid. A mixture of 3,3-difluoropiperidin-4-one hydrochloride, triethylamine (11.89 g, 117.52 mmol) and Boc anhydride (12.82 g, 58.75 mmol) in dry dichloromethane (100 mL) was stirred at room temperature for 16 h. After completion of the reaction (TLC), the reaction mixture was poured water extracted with dichloromethane (3 x 100 mL) ,dried over Na2SO4 and concentrated in vacuo to obtain the crude product which was purified by column chromatography over silica gel (60-120 mesh) using hexane/ethyl acetate (4:6) as eluent to get pure product. Colorless solid: m.p: 116-118 °C, (8.3 g, 90percent); 1H NMR: 400 MHz, DMSO-d6: δ 6.39 (s, 2H), 3.60 (t, J = 8.68 Hz, 2H), 3.35 (d, J = 7.40 Hz, 2H), 1.67 (s, 2H), 1.39 (s, 9H); MS: m/z 236.2 (M+1). 13C NMR (DMSO-d6, 400 MHz), δ (ppm): 181.6, 154.2, 112.3, 79.6, 50.6, 44.2, 30.8, 25.7, 25.7, 25.7. IR (KBr) 3262, 2983, 2937, 1669, 1430, 1395, 1369, 1342, 1279, 1158, 1211, 1123, 1093, 1058, 999, 975, 908, 879, 858, 834, 767, 704 cm-1. Anal. Calcd for C10H15F2NO3: C, 51.06; H, 6.43; N, 5.95. Found: C, 51.18; H, 6.51; N, 5.99.#10;
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 11, p. 1424 - 1427
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