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[ CAS No. 60899-34-5 ] {[proInfo.proName]}

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Chemical Structure| 60899-34-5
Chemical Structure| 60899-34-5
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Product Details of [ 60899-34-5 ]

CAS No. :60899-34-5 MDL No. :MFCD01111989
Formula : C10H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :SCTBWJINDJVNDM-UHFFFAOYSA-N
M.W : 157.17 Pubchem ID :2751583
Synonyms :

Calculated chemistry of [ 60899-34-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.2
TPSA : 40.86 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) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.59
Log Po/w (XLOGP3) : 1.38
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.0
Log Po/w (SILICOS-IT) : 2.72
Consensus Log Po/w : 1.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.05
Solubility : 1.39 mg/ml ; 0.00883 mol/l
Class : Soluble
Log S (Ali) : -1.84
Solubility : 2.27 mg/ml ; 0.0144 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.19
Solubility : 0.102 mg/ml ; 0.000649 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 60899-34-5 ]

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 [ 60899-34-5 ]

* 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 [ 60899-34-5 ]
  • Downstream synthetic route of [ 60899-34-5 ]

[ 60899-34-5 ] Synthesis Path-Upstream   1~8

  • 1
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  • [ 15115-60-3 ]
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YieldReaction ConditionsOperation in experiment
60% at 95℃; for 7 h; Inert atmosphere [0435] l-oxo-2,3-dihydro-lH-indene-4-carbonitrile (INT-45)[0436] To a stirring solution of 4-bromo-2,3-dihydro-lH-inden-l-one (100.0 g, 0.48 mol) in150 mL of l-methy-2-pyrrolidine (NMP) was added zinc cyanide (111.8 g, 0.95 mol) and tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] (2.75 g, 0.024 mol). The solution was degassed with N2 and the reaction mixture heated at 95°C for 7 h. Upon cooling, the reaction mixture was poured onto ice water (3.5 L). The compound and inorganic Zn salts precipitated. The solid was collected and partitioned between DCM and water. The organic layers were filtered to remove the Zn salts, and the filtrate was concentrated and crystallized from a 4:1 mixture of EtOH and MeOH (400 mL) to give 45.5 g (60 percent) of l-oxo-2,3- dihydro-lH-indene-4-carbonitrile INT-45 as a light yellow solid. LCMS-ESI (m/z) calculated for C10H7NO: 157.2; found 158.1 [M+H]+, tR = 2.67 min. 1H NMR (400 MHz, CDC13) 6 8.00 - 7.90 (m, 1H), 7.86 (dd, J = 7.5, 1.1, 1H), 7.50 (t, J = 7.6, 1H), 3.40 - 3.19 (m, 2H), 2.90 - 2.61 (m, 2H). 13C NMR (101 MHz, CDC13) δ 204.70, 157.90, 138.38, 137.88, 128.44, 128.28, 116.31, 111.70, 36.01, 25.49.
60% With tetrakis(triphenylphosphine) palladium(0) In 1-methyl-pyrrolidin-2-one at 95℃; for 7 h; Inert atmosphere To a stirred solution of 4-bromo-2,3-dihydro-lH-inden-l-one (100.0 g, 0.48 mol) in 150 mL of l-methy-2-pyrrolidine (NMP) was added zinc cyanide (111.8 g, 0.95 mol) and tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] (2.75 g, 0.024 mol). The solution was degassed with N2 and the reaction mixture heated at 95°C for 7 h. Upon cooling, the reaction mixture was poured onto ice water (3.5 L). The compound and inorganic Zn salts precipitated. The solid was collected and partitioned between DCM (3 X 100 mL) and water. The organic layers were filtered to remove the Zn salts, and the filtrate was concentrated and crystallized from a 4: 1 mixture of EtOH and MeOH (400 mL) to give 45.5 g (60 percent) of l-oxo-2,3-dihydro-7H-indene-4-carbonitrile INT-1 as a light yellow solid. LCMS-ESI (m/z) calculated for Ci0H7NO: 157.2; found 158.1 [M+H]+, tR = 2.67 min. 1H NMR (400 MHz, CDC13) δ 8.00 - 7.90 (m, 1H), 7.86 (dd, J = 7.5, 1.1, 1H), 7.50 (t, J = 7.6, 1H), 3.40 - 3.19 (m, 2H), 2.90 - 2.61 (m, 2H). 13C NMPv (101 MHz, CDC13) δ 204.70, 157.90, 138.38, 137.88, 128.44, 128.28, 116.31, 111.70, 36.01, 25.49.
60% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 165℃; for 1 h; Microwave irradiation To a solution of 4-bromo-2,3-dihydroinden-1-one SM1 (1 g, 4.74 mol) in DMF (5 mL) were added Zn(CN)2 (0.55 g, 4.74 mmol) and Pd(PPh3)4 (0.14 g, 0.12 mmol), the reaction mixture was under microwave irradiation for 1 hour at 165 °C . The solvent was removed under reduced pressure. The cmde was purified by flash chromatography on silica gel using a mixture of (PE/EtOAc 5:1) as eluent to afford compound 1 (0.45 g, 60percent) as an solid. LC-MS: m/z =158[M+H]
60% With tetrakis(triphenylphosphine) palladium(0) In 1-methyl-pyrrolidin-2-one at 95℃; for 7 h; Inert atmosphere To a stirred solution of 4-bromo-2,3-dihydro-1H-inden-1-one (100.0 g, 0.48 mol) in 150 mL of 1-methy-2-pyrrolidine (NMP)was added zinc cyanide (111.8 g,0.95 mol) and tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] (2.75 g, 0.024 mol).The solution was degassed with N2 and the reaction mixture heated at 95°C for 7 h. Upon cooling, the reaction mixture was poured onto ice water (3.5 L). The compound and inorganic Zn salts precipitated. The solid was collected and partitioned between DCM (3 X 100 mL) and water. The organic layers were filtered to remove the Zn salts, and the filtrate was concentrated and crystallized from a 4:1 mixture of EtOH andMeOH (400 mL) to give 45.5 g (60 percent) of 1-oxo-2,3-dihydro-JH-indene-4-carbonitrile INT-1 as a light yellow solid. LCMS-ESI (m/z) calculated for C,0H7N0: 157.2; found 158.1 [M+H], tR = 2.67 mm. ‘H NIVIR (400 MHz, CDC13) 8.00 — 7.90 (m, 1H), 7.86 (dd, J 7.5, 1.1, 1H), 7.50 (t, J= 7.6, 1H), 3.40—3.19 (m, 2H), 2.90—2.61 (m, 2H).‘3CNIVIR(1o1 MHz, CDCl3)204.70, 157.90, 138.38, 137.88, 128.44, 128.28, 116.31,111.70, 36.01, 25.49.
0.18 g at 150℃; for 1 h; Microwave irradiation To a solution of 4-bromo-2,3-dihydro-1H-inden-1-one (300 mg, 1.4214 mmol) in dimethylamine (3 mL) was added dicyanozinc (0.1669 g, 1.4214 mmol) and Pd(PPh3)4 (0.0822 g, 0.0711 mmol). The reaction was stirred at 150 °C in microwave for 1 h. Water (20 mL) was added to the reaction vessel and the resulting biphasic mixture was transferred to a separatory funnel. The layers were separated and the aqueous phase was extracted with EtOAc (3 x 20 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resulting oil was purified by flash column chromatography with a gradient elution of EtOAc (5percent) and hexane (95percent) to EtOAc (10percent) and EtOAc (90percent) to provide 1-oxo-2,3-dihydro-1H-indene-4-carbonitrile (0.18 g, 1.1453 mmol) as a white solid.

Reference: [1] Patent: WO2011/60389, 2011, A1, . Location in patent: Page/Page column 87-88
[2] Patent: WO2015/66515, 2015, A1, . Location in patent: Page/Page column 68
[3] Patent: WO2016/44770, 2016, A1, . Location in patent: Page/Page column 578
[4] Patent: WO2018/64356, 2018, A1, . Location in patent: Page/Page column 51
[5] Patent: WO2010/129379, 2010, A1, . Location in patent: Page/Page column 72
[6] Patent: EP2632465, 2015, B1, . Location in patent: Paragraph 0139
[7] Patent: WO2018/26371, 2018, A1, . Location in patent: Paragraph 0262
  • 2
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YieldReaction ConditionsOperation in experiment
64% With copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 16 h; l-oxo-2,3-dihydro-lH-indene-4-carbonitrile: To a solution of 4-bromo-2,3- dihydro-lH-inden-l-one (50 g, 236.91 mmol, 1.00 equiv) in N,N-dimethylformamide (250 mL) was added CuCN (63.67 g, 710.92 mmol, 3.00 equiv), Cul (4.5 g, 23.63 mmol, 0.10 equiv). The resulting solution was stirred for 16 h at 120 °C. The reaction mixture was cooled. The resulting solution was diluted with water (700 mL). The solids were filtered out. The resulting solution was extracted with ethyl acetate (4 x 300 mL) and the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:2) to afford 24 g (64percent) of l-oxo-2,3-dihydro-lH-indene-4-carbonitrile as a light brown solid.
60% at 20℃; for 22 h; Reflux To a solution of 4-bromo-1-indanone (10 g, 47.37 mmol) in DMF (100 mL) was added CuCN (12.72 g, 142.11 mmol) and the reaction mixture heated under reflux for 6h. The reaction mixture was cooled to RT and stirred for 16h. The reaction mixture was filtered through Celite®, and washed with EtOAc. The combined filtrate was diluted with EtOAc(500 mL) and washed with ice-water (3 x 300 mL) and the combined organic layers were washed with brine, dried over Na2504 and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with 10-20percent EtOAc/pet. ether to afford 1-oxo-indan-4-carbonitrile (4.5 g, 60percent) as a yellow solid.Rt: 0.6 (30percent EtOAc/pet ether).1H NMR (400MHz, CDCI3): O 7.97 (d, J= 7.6 Hz, 1H), 7.89 (dd, J= 6.0, 1.2 Hz, 1H), 7.52 (dd, J= 4.4, 3.6 Hz, 1H), 3.33 (t, J= 6.0 Hz, 2H), 2.82-2.79 (m, 2H).
Reference: [1] Patent: WO2016/164180, 2016, A1, . Location in patent: Paragraph 00146
[2] Patent: WO2015/36759, 2015, A1, . Location in patent: Page/Page column 172
  • 3
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Reference: [1] Patent: US5902803, 1999, A,
[2] Patent: US5789406, 1998, A,
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1934, vol. <2> 139, p. 94
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1934, vol. <2> 139, p. 94
  • 6
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1934, vol. <2> 139, p. 94
  • 7
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  • [ 1306763-30-3 ]
Reference: [1] Patent: WO2011/60389, 2011, A1,
[2] Patent: WO2018/64356, 2018, A1,
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  • [ 1306763-29-0 ]
Reference: [1] Patent: WO2011/60389, 2011, A1,
[2] Patent: WO2018/64356, 2018, A1,
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