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Chemical Structure| 98977-36-7
Chemical Structure| 98977-36-7
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Product Details of [ 98977-36-7 ]

CAS No. :98977-36-7 MDL No. :MFCD01631193
Formula : C10H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :RIFXIGDBUBXKEI-UHFFFAOYSA-N
M.W : 199.25 Pubchem ID :2756825
Synonyms :

Calculated chemistry of [ 98977-36-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.79
TPSA : 46.61 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) : -6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 1.02
Log Po/w (WLOGP) : 1.21
Log Po/w (MLOGP) : 0.76
Log Po/w (SILICOS-IT) : 1.14
Consensus Log Po/w : 1.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.52
Solubility : 6.02 mg/ml ; 0.0302 mol/l
Class : Very soluble
Log S (Ali) : -1.59
Solubility : 5.14 mg/ml ; 0.0258 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.4
Solubility : 7.97 mg/ml ; 0.04 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 98977-36-7 ]

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

Application In Synthesis of [ 98977-36-7 ]

* 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 [ 98977-36-7 ]
  • Downstream synthetic route of [ 98977-36-7 ]

[ 98977-36-7 ] Synthesis Path-Upstream   1~35

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Reference: [1] Patent: WO2017/216726, 2017, A1,
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  • [ 40864-10-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 15, p. 4667 - 4678
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  • [ 23396-50-1 ]
Reference: [1] Patent: US2013/178612, 2013, A1,
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  • [ 107-21-1 ]
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  • [ 40369-91-3 ]
Reference: [1] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 65
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Reference: [1] Patent: WO2010/59771, 2010, A1, . Location in patent: Page/Page column 47
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Reference: [1] Process Biochemistry, 2017, vol. 56, p. 90 - 97
[2] Patent: WO2017/216726, 2017, A1, . Location in patent: Page/Page column 734
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YieldReaction ConditionsOperation in experiment
99.4% With sodium hypochlorite solution; sodium hydrogencarbonate; potassium bromide In dichloromethane at 5 - 10℃; In the step 2, the compound N-BOC-3-piperidone is prepared according to the following scheme:To the reaction flask was added 20.1 g of N-BOC-3-hydroxypiperidine,703.5 mg of PS-ABNO,100 ml of dichloromethane,1g of potassium bromide dissolved in water was added to the reaction system,Cooled to 5 ° C with an ice bath,8.4 g of NaHCO3 was dissolved in 100 ml of sodium hypochlorite solution,Adjust its pH = 8.5 or so,Slowly added to control the drip rate so that the reaction temperature is not higher than 10 , after the addition was completed,TLC detection, the reaction was completed, the recovery of PS-ABNO filtration, the reaction liquid was separated and the aqueous phase was extracted with 100ml of dichloromethane, the organic phase was combined, washed once with 100ml of water, the organic phase was dried over anhydrous Na2SO4, filtered, Concentration of 19.8g of light yellow oily product, to obtain the target product N-BOC-3-piperidone, yield 99.4percent
97% With Dess-Martin periodane In dichloromethane at 20℃; for 22 h; Inert atmosphere To a solution of 3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (Compound 3a) (0.25 g; 1.24 mmol) in anhydrous dichloromethane (9.0 mL) at 0° C. was added 1,1,1-tris(actyloxy)-1,1-dihydro-1,2-benzodioxol-3-(1H)-one (1.58 g; 3.72 mmol). The mixture was allowed to stir at room temperature under nitrogen for 2 h, to which was then added additional 1,1,1-tris(actyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (0.5 g; 1.18 mmol). Upon stirring for 20 h at room temperature, the reaction mixture was partitioned between dichloromethane and brine. The organic layer was washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash column chromatography, eluting with 40percent ethyl acetate in hexanes, to yield Compound 3b as an oil (0.24 g; 97percent yield). 1H NMR (400 MHz, CDCl3): δ 4.0 (2H, br s), 3.60-3.57 (2H, m), 2.49-2.45 (2H, m), 2.01-1.95 (1H, m), 1.46 (9H, s).
95% With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In diethyl ether; water; toluene at 0 - 4℃; 2) Synthesis of 3-oxo-piperidine-l-carboxylic acid t-butyl ester3-hydroxy-piperidine-l-carboxylic acid t-butyl ester (4.0 g, 20 mmol) synthesized in Section (1) was dissolved in a mixed solution (2:1:2, 100 niL) of toluene, water and ethyl ester, and 1.0 molpercent TEMPO (31 mg), and NaBr (2.3 g) were sequentially added thereto. A mixture of NaHCψ3 (4.7 g) and NaOCl (5percent, 36 mL) was slowly added to the mixture under cooling conditions (0 to 4°C). After the reaction was complete, the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtered organic layer was concentrated under reduced pressure to afford 3.8 g (yield: 95percent) of the title compound.1H NMR (500 MHz, CDCl3) δl.47 (s, 9H), 1.98 (m, 2H), 2.47 (t, J=6.7 Hz, 2H), 3.59 (t, J=6.1 Hz, 2H), 4.00 (bs, 2H).
86% With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 18 h; Step 1 tert-butyl 3-oxopiperidine-1 -carboxylate Boc o [00251] To a solution of tert-butyl 3-hydroxypiperidine-1 -carboxylate (5 g, 24.84 mmol, 1.0 equiv) in DCM (125 mL) was added Dess-Martin periodinane (11.59 g, 27.33 mmol, 1.1 equiv) at 0 °C in a few portions. The solution was stirred at 0 °C for a while and allowed to warm to room temperature slowly. The solution was stirred at room temperature for 18 hrs. A lot of white solid suspended. The white solid was removed by filtration, eluted with EtOAc (100 mL). The combined organic phase was washed with saturated solution of NaHCO3 (50 mL), dried over anhydrous Na2SO4, concentrated to afford 4.28 g ( yield 86percent) of tert-butyl 3-oxopiperidine-1 -carboxylate as a white solid. [00252] 1H NMR (CDCI3, 400 MHz): δ 4.01 (s, 2 H), 3.59 (t, 2 H), 2.47 (t, 2 H), 1.98 (m, 2 H), 1.47 (s, 9 H).
75% With 4-methylmorpholine N-oxide In dichloromethane at 0 - 20℃; for 1.33333 h; [0174] To a 0° C. solution of 3-hydroxypiperidine (2.12 g, 21.0 mmol) in EtOH (20 mL) was added NEt3 (5.6 mL, 40.2 mmol), followed by a solution of (Boc)2O (5.03 g, 23.0 mmol) in EtOH (20 mL). The reaction stirred at room temperature for one hour, and then the solvent was evaporated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and washed with 10percent citric acid (50 mL), water (50 mL) and brine (50 mL). The organic solution was dried (MgSO4), filtered and evaporated under reduced pressure to afford the crude product as a white solid (3.55 g, 17.6 mmol, 84percent). 1H NMR (CDCl3) δ 1.45 (s, 9H), 1.48-1.52 (m, 2H), 1.72-1.78 (m, 1H), 1.84-1.94 (m, 1H), 2.12 (br. s, 1H), 3.01-3.12 (m, 2H), 3.46-3.59 (m, 1H), 3.65-3.78 (m, 2H). [0175] Preparation of Tert-Butyl 3-oxo-1-piperidinecarboxylate: [0176] To a 0° C. solution of the alcohol (2.01 g, 10.0 mmol) in CH2Cl2 (50 mL) was added crushed 3A molecular sieves (5.26 g), 4-methylmorpholine-N-oxide (1.76 g, 15.0 mmol) and tetrapropylammonium perruthenate (357 mg, 1.02 mmol). The resulting black solution was stirred at 0° C. for 20 minutes, then at room temperature for a further one hour. The mixture was filtered through a plug of silica, rinsed with EtOAc and the concentrated filtrate was purified by flash chromatography on silica gel (EtOAc/hexane, 1:1) to afford the ketone as a yellow liquid (1.49 g, 7.48 mmol, 75percent). 1H NMR (CDCl3) δ 1.46 (s, 9H), 1.98 (ddd, 2H, J=12.3, 6.5, 6.0 Hz), 2.47 (t, 2H, J=6.5 Hz), 3.58 (t, 2H, J=6.0 Hz), 4.00 (s, 2H). [0177] Preparation of Tert-Butyl 3-(5,6,7,8-tetrahydroquinolin-8-ylamino)-piperidine-1-carboxylate: [0178] To a solution of 8-amino-5,6,7,8-tetrahydroquinoline (1.00 g, 6.75 mmol) in MeOH (30 mL) was added a solution of the ketone (1.40 g, 7.03 mmol) in MeOH (20 mL). The reaction stirred at room temperature for 16 hours. NaBH4 (848 mg, 22.4 mmol) was added and the mixture stirred for a further 45 minutes. The solvent was evaporated under reduced pressure, and the residue was taken up into CH2Cl2 (50 mL) and washed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL). The organic solution was dried (MgSO4), filtered and evaporated under reduced pressure. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 9:1:0.5) gave a brown oil which, following a second purification (CH2Cl2/MeOH, 97:3) afforded the amine as a yellow oil (638 mg, 1.92 mmol, 28percent). 1H NMR (CDCl3) δ 1.22-1.40 (m, 2H), 1.47 (s, 9H), 1.65-1.81 (m, 3H), 1.91-2.04 (m, 2H), 2.11-2.25 (m, 2H), 2.44-2.65 (m, 1H), 2.65-2.90 (m, 4H), 3.88-4.05 (m, 2H), 4.05-4.31 (m, 1H), 7.06 (dd, 1H, J=7.7, 4.7 Hz), 7.36 (d, 1H, J=7.8 Hz), 8.37 (d, 1H, J=4.3 Hz). [0179] Preparation of COMPOUND 8: [0180] A mixture of this amine (247 mg, 0.75 mmol), tert-butyl 2-chloromethyl-benzimidazole-1-carboxylate (238 mg, 0.89 mmol), DIPEA (0.20 mL, 1.2 mmol) and KI (14 mg, 0.08 mmol) in CH3CN (4 mL) was heated at 60° C. for 20 hours. After cooling, the reaction was diluted with saturated aqueous NaHCO3 (10 mL) and extracted with CH2Cl2 (25 mL.x.3). The organic solution was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting dark red oil was purified by flash column chromatography on silica gel (CH2Cl2/MeOH, 9:1) giving an orange foam. A second purification (CH2Cl2/MeOH, 19:1) gave the tertiary amine as an orange solid (83 mg, 20percent). [0181] This material was stirred in TFA (1.5 mL) at room temperature for 2 hours, and then the excess solvent was evaporated under reduced pressure. The residue was taken up into CH2Cl2 (20 mL) and washed with saturated aqueous NaHCO3 (10 mL). The aqueous solution was extracted with CH2Cl2 (20 mL.x.2) and the combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 89:10:1) gave an approximately 2:1 mixture of diastereomers of the free amine as a yellow foam (21 mg, 0.06 mmol, 41percent). [0182] To a solution of this material (20 mg, 0.055 mmol) in glacial HOAc (1 mL) was added a saturated HBr in HOAc solution (0.5 mL). The reaction stirred at room temperature for 40 minutes. Et2O (2 mL) was added, the suspension was stirred and the solvent was decanted. The precipitate was washed with Et2O (1 mL.x.5), then dried under reduced pressure giving COMPOUND 8 as a yellow solid (26 mg, 0.038 mmol, 70percent). 1H NMR (D2O) δ 1.61-1.94 (m, 3H), 1.98-2.11 (m, 1H), 2.11-2.17 (m, 2H), 2.17-2.49 (m, 1H), 2.80-2.92 (m, 1H), 2.93-3.01 (m, 2H), 3.09-3.25 (m, 2H), 3.31-3.40 (m, 1H), 3.82-3.90 (m, 1H), 4.43 (d, 1H, J=16.5 Hz), 4.55 (d, 1H, J=16.5 Hz), 4.55-4.65 (m, 1H), 7.53-7.60 (m, 2H), 7.67-7.77 (m, 3H), 8.20 (d, 0.67H, J=7.8 Hz), 8.23 (d, 0.33H, J=7.8 Hz), 8.51 (d, 0.67H, J=5.7 Hz), 8.55 (d, 0.33H, J=5.7 Hz). 13C NMR (D2O) δ 20.5 and 20.6, 21.9 and 22.1, 24.2 and 24.5, 26.8 and 27.5, 28.0, 43.2, 44.0, 46.2 and 47.0, 58.5 and 59.2, 114.4, 125.8, 126.8, 131.7, 139.5, 140.5 and 141.6, 147.7 and 147.8, 150.6 and 151.2. ES-MS m/z 362 (M+H). Anal. Calcd. for C22H27N5.3.1HBr.1.8H2O.0.3C4H10O: C, 41.78; H, 5.55; N, 10.50; Br, 37.14. Found: C, 41.48; H, 5.44; N, 10.44; Br, 37.50.
19% With pyridinium chlorochromate In dichloromethane at 20℃; for 3.25 h; Example 1: Tert-butyl 3-r3-(cyclopentyloxyV4-methoxyphenvn-l-oχa-2J- diazaspiror4.51dec-2-ene-7-carboxylate CCompound No. 21*)Step a: Synthesis of 3-oxo-piperidine-l-carboxyIic acid tert-butyl esterTo a solution of the compound 3-hydroxy-piperidinyl-l-carboxylic acid tert-butyl ester (7.5 gm, 37.3 mmole) in dichloromethane (100 niL) was added celite (5.0 grn) and stirred at room temperature for 10 minutes. Pyridinium chlorochromate (9.57 gm, 44.4 mmole) was added portionwise over a period of 5 minutes. The reaction mixture was stirred at room temperature for 3 hours. Dichloromethane was removed under reduced pressure followed by the addition of ethyl acetate. The resulting reaction mixture was again stirred for 10 minutes and filtered through celite pad. The organic layer was removed under reduced pressure. The residue thus obtained was purified by column chromatography to furnish the title compound. Yield: 1.4 gm, 19 percent

Reference: [1] Patent: CN107573278, 2018, A, . Location in patent: Paragraph 0055; 0059-0061; 0076-0077
[2] Patent: US2011/105520, 2011, A1, . Location in patent: Page/Page column 36
[3] Patent: WO2009/82134, 2009, A2, . Location in patent: Page/Page column 37
[4] Patent: WO2013/13308, 2013, A1, . Location in patent: Paragraph 00250-00252
[5] Patent: US2003/220341, 2003, A1, . Location in patent: Page/Page column 15-16
[6] Patent: WO2006/85212, 2006, A2, . Location in patent: Page/Page column 44
[7] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 6, p. 811 - 814
[8] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 20, p. 2691 - 2696
[9] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 13, p. 1785 - 1789
[10] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2155 - 2158
[11] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 7, p. 1645 - 1649
[12] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2115 - 2137
[13] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 2, p. 1022 - 1033
[14] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 1, p. 350 - 364
[15] Chemical and pharmaceutical bulletin, 2003, vol. 51, # 4, p. 390 - 398
[16] Patent: EP1375496, 2004, A1, . Location in patent: Page 42-43
[17] Tetrahedron Letters, 2011, vol. 52, # 5, p. 588 - 591
[18] Journal of Organic Chemistry, 2013, vol. 78, # 23, p. 11656 - 11669
[19] Patent: CN105949113, 2016, A, . Location in patent: Paragraph 0021; 0025
[20] Patent: EP1550660, 2005, A1, . Location in patent: Page/Page column 10
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Reference: [1] Patent: US2003/229094, 2003, A1, . Location in patent: Page 123
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YieldReaction ConditionsOperation in experiment
84.2%
Stage #1: With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol; water at 20℃; for 2 h;
Stage #2: With N-ethyl-N,N-diisopropylamine In methanol; water for 0.5 h;
Stage #3: at 20℃; for 5 h;
84.2 g (0.45 mol) of the above product was dissolved in 500 mL of methanol in a 1 L three-necked flask, 47.4 g (0.47 mol, 36percent) of concentrated hydrochloric acid was added dropwise, and 10percent palladium carbon 8.4 g was added. , and then into the hydrogen, stirring at room temperature for 2 hours, GC reaction was complete, the palladium carbon catalyst was filtered out, the filtrate was added 143.8g diisopropylethylamine, stirred for 30 minutes, 149.7g di-tert-butyl dicarbonate was added dropwise (0.67 mol), stirring at room temperature for 5 hours, disappearance of starting material by GC, concentration of the solvent under reduced pressure, adding 600 mL of ethyl acetate and 100 mL of 0.5 mol/L hydrochloric acid aqueous solution to the residue, and washing the organic layer with 100 mL of saturated sodium bicarbonate solution. The solvent was concentrated under pressure and added to n-heptane and stirred at -5 to 0°C to crystallize. After filtration, 74.7 g of N-Boc-3-piperidone was obtained as a slightly yellow solid. The yield was 84.2percent. GC purity: 98.8percent,
Reference: [1] Patent: CN107698493, 2018, A, . Location in patent: Paragraph 0043; 0047; 0051; 0055; 0059; 0063
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YieldReaction ConditionsOperation in experiment
68% With 2,6-dimethylpyridine; sodium periodate; ruthenium(III) chloride trihydrate In dichloromethane; water; acetonitrile at 20℃; for 1 h; Inert atmosphere General procedure: The alkene (1.16 mmol, 1 equivalent) was dissolved in a vigorously stirred mixture of DCM (7 mL) and acetonitrile (7 mL) under nitrogen. 2,6-Lutidine (0.27 mL, 2.32 mmol, 2 equivalents), water (10.5 mL) and sodium periodate (993 mg, 4.64 mmol, 4 equivalents) were then added sequentially. The reaction concentration with respect to the alkene was 0.047 M in a mixture of 1: 1: 1.5 - DCM: acetonitrile: water. To the resulting mixture a stock solution of ruthenium(III) chloride trihydrate (0.035 M in water) (1.16 mL, 0.04 mmol, 3.5 mol percent) was added dropwise via a syringe forming a brown suspension. The reaction was stirred vigorously at 20 °C for 1 h (or for the time indicated in the Tables 2 and 3). The reaction was diluted with water (20 mL) then extracted with DCM (3 x 20 mL). The organic extracts were combined then washed with brine (20 mL), passed through a phase separating cartridge and the volatiles were removed under reduced pressure. The resulting residue was purified by flash silica chromatography (EtOAc / heptane) to afford the ketone.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 51, p. 4479 - 4482
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YieldReaction ConditionsOperation in experiment
78% With ammonium chloride; trimethylamine In dichloromethane; dimethyl sulfoxide 115b)
tert-Butyl 3-oxopiperidine-1-carboxylate
DMSO (5.42 ml) was added dropwise to a solution of oxalyl chloride (5.01 ml) in methylene chloride (150 ml) at -78° C. and the mixture was stirred for 10 minutes.
Then, a solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (5.78 g) obtained in Example 115a) in methylene chloride (10 ml) was added dropwise thereto.
After stirring the mixture the same temperature for 10 minutes, the temperature was raised to -45° C. and the mixture was stirred for further 1 hour.
Trimethylamine (30 ml) was added to the reaction mixture and the mixture was stirred at 0° C. for 20 minutes.
An aqueous saturated ammonium chloride solution was added to the mixture and the mixture was extracted with methylene chloride.
The extract was dried over anhydrous sodium sulfate and concentrated and the residue was purified by a silica gel column to obtain the title compound as colorless crystals (4.5 g, 78percent).
NMR (CDCl3) δ: 1.47 (9H, s), 1.93-2.01 (2H, m), 2.46 (2H, t, J=6.8), 3.58 (2H, t, J=6.0), 4.00 (2H, s).
Reference: [1] Patent: US2003/187023, 2003, A1,
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Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 41, p. 5490 - 5492
[2] Organic Letters, 2009, vol. 11, # 16, p. 3566 - 3569
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Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 2, p. 224 - 229
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 2194 - 2211
[3] Patent: US2005/197373, 2005, A1, . Location in patent: Page/Page column 23
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Reference: [1] Patent: US2004/19058, 2004, A1,
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Reference: [1] Patent: US5902882, 1999, A,
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YieldReaction ConditionsOperation in experiment
95% With NaHCO3 In dichloromethane Example 161
Compound 161:
Preparation of (1H-Benzoimidazol-2-ylmethyl)-(2-piperidin-3-ylidene-ethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (hydrobromide salt).
To a solution of 3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.9169 g, 9.5 mmol) in CH2Cl2 (50 mL) was added Dess-Martin Periodinane (4.8470 g, 11.4 mmol), and the mixture was stirred at room temperature for 5 hours. CH2Cl2 (75 mL), saturated NaHCO3 (100 mL), and 20percent aqueous sodium thiosulfate (100 mL) were added, and the mixture was stirred for 30 minutes.
The layers were separated, and the aqueous layer was extracted with CH2Cl2 (1*75 mL).
The organic extracts were washed with brine (1*100 mL), dried (Na2SO4), and concentrated.
Purification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc) provided 1.80 g (95percent) of 3-oxo-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil. 1H NMR (CDCl3) δ 1.49 (s, 9H), 1.93-2.02 (m, 2H), 2.46 (t, 2H, J=6 Hz), 3.58 (t, 2H, J=6 Hz), 4.00 (s, 2H).
Reference: [1] Patent: US2004/19058, 2004, A1,
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Reference: [1] Synthesis, 2005, # 1, p. 92 - 96
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Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 2194 - 2211
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Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 2, p. 224 - 229
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Reference: [1] Analytical Chemistry, 2010, vol. 82, # 5, p. 2082 - 2086
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Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 1, p. 350 - 364
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 2, p. 1022 - 1033
[3] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2115 - 2137
[4] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 13, p. 1785 - 1789
[5] Tetrahedron Letters, 2011, vol. 52, # 5, p. 588 - 591
[6] Patent: EP1550660, 2005, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 1, p. 350 - 364
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 2, p. 1022 - 1033
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 7, p. 1645 - 1649
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YieldReaction ConditionsOperation in experiment
80% With morpholine; sulfur In ethanol at 90℃; General procedure: A mixture of cyclohexanone (1.06 mL, 10 mmol), ethyl cyanoacetate (1.15 mL, 10 mmol), morpholine (0.90 mL, 10 mmol), sulphur (0.32 g, 10 mmol) in ethanol (10 mL) was stirred and refluxed for overnight. After completion of the reaction, the reaction mixture was cooled to room temperature and the solvent was removed under vacuum. The crude solid was washed with cold ethanol and filtered though sintered funnel, dried under vacuum. The crude product was dissolved in dichloromethane and washed with brine. The organic layer was collected and concentrated under low vacuum to give the compound 2a; yield: 73percent (1.83 g);
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