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Chemical Structure| 206989-61-9
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Product Details of [ 206989-61-9 ]

CAS No. :206989-61-9 MDL No. :MFCD08437655
Formula : C12H21NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :HNVBBNZWMSTMAZ-UHFFFAOYSA-N
M.W : 227.30 Pubchem ID :10987983
Synonyms :

Calculated chemistry of [ 206989-61-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 66.41
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) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.7
Log Po/w (XLOGP3) : 1.29
Log Po/w (WLOGP) : 1.84
Log Po/w (MLOGP) : 1.33
Log Po/w (SILICOS-IT) : 1.47
Consensus Log Po/w : 1.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.8
Solubility : 3.62 mg/ml ; 0.0159 mol/l
Class : Very soluble
Log S (Ali) : -1.87
Solubility : 3.08 mg/ml ; 0.0135 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.62
Solubility : 5.49 mg/ml ; 0.0242 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 206989-61-9 ]

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 [ 206989-61-9 ]

* 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 [ 206989-61-9 ]
  • Downstream synthetic route of [ 206989-61-9 ]

[ 206989-61-9 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 206989-61-9 ]
  • [ 89895-06-7 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride In 1,4-dioxane; dichloromethane at 0℃; for 2 h; To a solution of Compound 3 (350 mg, 1.54 mmol) in anhydrous DCM (5 mL) was added HCl in dioxane (2 mL) at 0°C. The formed mixture was stirred for 2 h. The formed mixture was concectrated to give the desired product which was used for the next step (260 mg, 100percent).
95% With hydrogenchloride In methanol; water at 20℃; for 18 h; [0213] Tert-butyl 4-acetylpiperidine-1-carboxylate (3.29 g, 8.32 mmol) was dissolved in 30 ml of methanol.
To the resulting solution was slowly added 6N hydrochloric acid aqueous solution and the solution was stirred at room temperature for 18 hrs.
After removal of the solvent, acetone was added and the resulting solid was filtered to give the white title compound (4.36 g, 95.0 percent).
1H NMR (400 MHz, CDCl3) δ 3.14 (m, 2H), 2.64 (m, 2H), 2.43 (s, 1H), 2.40 (s, 3H), 1.85 (m, 2H), 1.50 (m, 2H).
Reference: [1] Patent: WO2013/96744, 2013, A1, . Location in patent: Page/Page column 192
[2] Patent: EP3255042, 2017, A2, . Location in patent: Paragraph 0209; 0213
  • 2
  • [ 75-16-1 ]
  • [ 139290-70-3 ]
  • [ 206989-61-9 ]
YieldReaction ConditionsOperation in experiment
96% at -78 - 0℃; To the solution of 11 (43.2, 158 mmol) in THF (1.3 L) at -78 °C was added methylmagnesium bromide (106 mL, 3 M, 317 mmol) dropwise. The solution was warmed to 0 °C for 1 h before it was quenched with a saturated ammonium chloride solution. To this mixture was added EtOAc (1000 mL) and the organic phase was washed with brine (500 mL x 2), dried over Na2SO4 to give 12 (34.8 g, 96percent) as an oil.
94% at -78 - 0℃; for 1 h; [0212] Tert-butyl-4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (2.29 g, 8.32 mmol) was dissolved in 30 ml of tetrahydrofuran (THF) and the resulting solution was cooled to -78 °C.
To the solution was slowly added methylmagnesium bromide (3.0 M) (7.73 ml, 10.82 mmol) and the solution was stirred at 0 °C for 1 hr.
After completion of the reaction by 2 N hydrochloric acid aqueous solution, 6 N sodium hydroxide solution was added to adjust pH to 10 and then the solution was extracted with dichloromethane.
The organic layer was treated with magnesium sulfate (MgSO4) and filtered and the solution was concentrated.
The resulting residue was isolated and purified by silica gel column chromatography (dichloromethane/methanol = 10/1) to give the white title compound (6.36 g, 94.0 percent).
1H NMR (400 MHz, CDCl3) δ 3.90 (m, 2H), 2.98 (s, 2H), 2.51 (s, 1H), 2.15(s, 3H), 1.67 (m, 4H), 1.49 (s, 9H).
82%
Stage #1: at 0℃; for 18 h;
Stage #2: With water In diethyl ether at 0℃; for 0.5 h;
b) f erf-butyl 4-acetylpiperidine-1-carboxylate Methyl magnesium bromide (3M in dietyhl ether, 2.45 ml_, 7.35 mmol) was dropwise added to an ice-cooled solution of the title compound of Preparation 55a (1g, 3.67 mmol) under argon and the mixture was stirred at that temperature for 18 hours. The reaction was quenched by the addition of ice and vigorously stirred for 30 minutes. The mixture was extracted with ethyl acetate, washed with brine and dried over sodium sulphate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica flash, using hexane/ethyl acetate (1:1) as eluents, to yield the title compound (680 mg, 82percent) as colourless oil.1H-NMR δ (CDCI3): 1.46 (s, 9H)1 1.41-1.62 (m, 2H), 1.78-1.88 (m, 2H), 2.17 (m, 3H), 2.38-2.54 (m, 1 H)1 2.71-2.86 (m, 2H), 4.05-4.15 (m, 2H).
80%
Stage #1: at 0℃; for 0.833333 h; Cooling with acetone-dry ice
Stage #2: With hydrogenchloride In diethyl ether; water
[00191] Step 2: A 3- neck, 250 mL round bottom flask was charged with a solution of tert-bvXyl 4-(methoxy(methyl)carbamoyl)piperidine-l-carboxylate (9.9 g) in Et2O (120 mL). The flask was purged with nitrogen and then cooled in a CO2 / acetone bath. Methylmagnesium bromide (26.8 mL of a 3.0 M solution in Et2O, 80 mmol) was added dropwise over 10 min to the amide. The resulting thick mixture was warmed to 0 0C and then stirred for 40 min before being poured into 2 M HCl solution (50 mL). The mixture was diluted with Et2O (100 mL), washed with brine, dried (MgSO4) and concentrated on a rotary evaporator to give tert-bvAyl A- acetylpiperidine-1-carboxylate (7.3 g, 32.1 mmol, 80 percent yield) as a colorless oil. The product partly crystallized on standing at RT. 1H-NMR (400 MHz, CDCl3) δ ppm 4.06 (2 H, s), 2.74 (2 H, s), 2.42 (1 H, s), 2.12 (2 H, s), 1.78 (2 H, s), 1.49 (2 H, s), 1.41 (9 H, s).
80%
Stage #1: at 0℃; for 0.833333 h; Cooling with acetone-dry ice
Stage #2: With hydrogenchloride In diethyl ether; water
[00191] Step 2: A 3- neck, 250 mL round bottom flask was charged with a solution of tert-bvXyl 4-(methoxy(methyl)carbamoyl)piperidine-l-carboxylate (9.9 g) in Et2O (120 mL). The flask was purged with nitrogen and then cooled in a CO2 / acetone bath. Methylmagnesium bromide (26.8 mL of a 3.0 M solution in Et2O, 80 mmol) was added dropwise over 10 min to the amide. The resulting thick mixture was warmed to 0 0C and then stirred for 40 min before being poured into 2 M HCl solution (50 mL). The mixture was diluted with Et2O (100 mL), washed with brine, dried (MgSO4) and concentrated on a rotary evaporator to give tert-bvAyl A- acetylpiperidine-1-carboxylate (7.3 g, 32.1 mmol, 80 percent yield) as a colorless oil. The product partly crystallized on standing at RT. 1H-NMR (400 MHz, CDCl3) δ ppm 4.06 (2 H, s), 2.74 (2 H, s), 2.42 (1 H, s), 2.12 (2 H, s), 1.78 (2 H, s), 1.49 (2 H, s), 1.41 (9 H, s).
77% at 20℃; Cooling INTERMEDIATE B5 foert-ButyM-acetylpiperidine-l-carboxylateK>i A 3 M solution of bromo(methyl)magnesium in diethylether (13.8 niL, 41.4 mmol) was cooled in an ice-bath and a solution of tert-butyi 4-[methoxy(methyl)amino]carbonyl}- piperidine-1-carboxylate (Intermediate B4; 5.2 g 19.2 mmol) in Et2O (25 mL) was added dropwise. The ice-bath was removed and the mixture was stirred at r.t. for 2 h. The excess bromo(methyl)magnesium was quenched by dropwise addition of water, and the water phase was then extracted with ether. Yield 3.35 g (77percent). Analytical HPLC: purity 95percent (System A); LRESIMS (ESI+) m/z = 172 (M+H-?Bu)+.
72% at 0 - 20℃; To a solution of Compound 2 (500 mg, 1.84 mmol) in anhydrous THF (5 mL) was added CMgBr (0.8 mL, 2.4 mmol) at 0 °C . The formed mixture was allowed to warm to room temperature. The reaction was quenched with aqueous NH4CI solution. The organic layer was separated and extracted with EtOAc (10 mLx2). The combined organic layers were concentrated to give the crude product, which was purified by column chromatography to give the desired product (300 mg, 72percent). lH NMR (400 MHz, CDCI3): δ ppm: 4.04(br, 2H), 2.73(t, 2H), 2.43(m, 1H), 2.15(s, 3H), 1.82(m, 2H), 1.53(m, 2H), 1.45(s, 9H).
62% at -78 - 20℃; for 4 h; [0269] To a stirred solution of tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-l- carboxylate (4.3 g, 15.8 mmol) in dry THF (20 mL) was added a solution of methyl magnesium bromide (20 mL, 23.71 mmol, 1.6 M in THF:toluene) at -78 °C and the reaction was stirred at -78 °C for 2 h and RT for 2 h. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with saturated NH4C1 solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2S04 and concentrated under reduced pressure to a crude residue which was purified by column chromatography to afford tert-butyl 4- acetylpiperidine-l-carboxylate (2.8 g, 62percent).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 935 - 939
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 5, p. 1299 - 1305
[3] Patent: EP3255042, 2017, A2, . Location in patent: Paragraph 0209; 0212
[4] Patent: WO2008/17461, 2008, A1, . Location in patent: Page/Page column 62
[5] Patent: WO2008/42925, 2008, A1, . Location in patent: Page/Page column 96
[6] Patent: WO2008/42925, 2008, A1, . Location in patent: Page/Page column 96
[7] Patent: WO2009/150144, 2009, A1, . Location in patent: Page/Page column 139
[8] Patent: WO2013/96744, 2013, A1, . Location in patent: Page/Page column 191
[9] Patent: WO2016/40498, 2016, A1, . Location in patent: Paragraph 0269
[10] Patent: US2004/2504, 2004, A1, . Location in patent: Page/Page column 23; 38
[11] Angewandte Chemie - International Edition, 2017, vol. 56, # 23, p. 6646 - 6650[12] Angew. Chem., 2017, vol. 56, # 23, p. 6646 - 6650,5
[13] Patent: WO2018/33135, 2018, A1, . Location in patent: Paragraph 0102-0103
[14] Patent: TW2018/11794, 2018, A, . Location in patent: Paragraph 0055; 0091; 0095
[15] Patent: WO2018/137681, 2018, A1, . Location in patent: Paragraph 00137; 00138
  • 3
  • [ 139290-70-3 ]
  • [ 206989-61-9 ]
YieldReaction ConditionsOperation in experiment
94.7% With methylmagnesium bromide In tetrahydrofuran at -78 - 25℃; for 16 h; To a solution of tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1- carboxylate (10.0 g, 36.76 mmol) in THF (150 mL) was added MeMgBr (24.5 mL, 73.52 mmol) at -78 C. The mixture was stirred at 25 C for 16 h.. TLC showed the reaction worked well. The mixture was quenched with aq. NH4Cl and H2O (100 mL) was added. The mixture was extracted with DCM (100 mL x 3). The DCM layer was dried and evaporated to give the tert-butyl 4-acetylpiperidine-1-carboxylate (7.9 g, yield: 94.7 percent).
Reference: [1] Patent: KR2017/45749, 2017, A, . Location in patent: Paragraph 0614; 0620-0622
[2] Patent: WO2004/41777, 2004, A2, . Location in patent: Page 54-55
[3] Patent: US6140333, 2000, A,
  • 4
  • [ 479630-08-5 ]
  • [ 206989-61-9 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide In water for 20 h; Reflux In a 100 mL round-bottomed flask filled with a solution of 6.0 M NaOH (50 mL) was added 6 (9.00 g 30.2 mmol). The reaction mixture was heated under reflux for 20 h, then diluted with 300 mL water and was quenched by addition 240 mL dichloromethane. The collected organic layers were washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure, affording 6.42 g (94.0 percent yield) light yellow liquid. 1H NMR (300 MHz, CDCl3): δ 4.07–4.11 (m, 2H), 2.74–2.81 (m, 2H), 2.41–2.48 (m, 1H), 2.15 (s, 3H), 1.81–1.84 (m, 2H), 1.48–1.57 (m, 2H), 1.44 (s, 9H).
Reference: [1] Tetrahedron, 2015, vol. 71, # 42, p. 8208 - 8212
  • 5
  • [ 75-16-1 ]
  • [ 91419-52-2 ]
  • [ 206989-61-9 ]
Reference: [1] Patent: WO2004/99178, 2004, A1, . Location in patent: Page 39
  • 6
  • [ 676-58-4 ]
  • [ 139290-70-3 ]
  • [ 206989-61-9 ]
Reference: [1] Patent: WO2009/45382, 2009, A1, . Location in patent: Page/Page column 33
[2] Patent: WO2004/41279, 2004, A1, . Location in patent: Page/Page column 69
  • 7
  • [ 84358-13-4 ]
  • [ 206989-61-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3419 - 3424
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 935 - 939
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 5, p. 1299 - 1305
[4] Patent: WO2013/96744, 2013, A1,
[5] Tetrahedron, 2015, vol. 71, # 42, p. 8208 - 8212
[6] Patent: WO2016/40498, 2016, A1,
[7] Patent: KR2017/45749, 2017, A,
[8] Patent: EP3255042, 2017, A2,
[9] Patent: WO2018/33135, 2018, A1,
[10] Patent: TW2018/11794, 2018, A,
[11] Patent: WO2018/137681, 2018, A1,
[12] Patent: WO2009/150144, 2009, A1,
[13] Patent: WO2008/42925, 2008, A1,
  • 8
  • [ 917-64-6 ]
  • [ 91419-52-2 ]
  • [ 206989-61-9 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 7, p. 822 - 829
  • 9
  • [ 24424-99-5 ]
  • [ 206989-61-9 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 7, p. 822 - 829
[2] Patent: EP3255042, 2017, A2,
  • 10
  • [ 39546-32-2 ]
  • [ 206989-61-9 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 7, p. 822 - 829
  • 11
  • [ 91419-48-6 ]
  • [ 206989-61-9 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 7, p. 822 - 829
  • 12
  • [ 782493-40-7 ]
  • [ 206989-61-9 ]
Reference: [1] Tetrahedron, 2015, vol. 71, # 42, p. 8208 - 8212
  • 13
  • [ 124443-68-1 ]
  • [ 206989-61-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 23, p. 6646 - 6650[2] Angew. Chem., 2017, vol. 56, # 23, p. 6646 - 6650,5
  • 14
  • [ 498-94-2 ]
  • [ 206989-61-9 ]
Reference: [1] Patent: EP3255042, 2017, A2,
  • 15
  • [ 917-64-6 ]
  • [ 139290-70-3 ]
  • [ 206989-61-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3419 - 3424
  • 16
  • [ 206989-61-9 ]
  • [ 301221-79-4 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With chloro-trimethyl-silane; lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃;
Stage #2: With bromine In tetrahydrofuran at -78 - 20℃;
INTERMEDIATE B6 tert-Butyl 4-(bromoacetyl)piperidine-l-carboxylate To a cooled (-78 0C) suspension of tert-butyi 4-acetylpiperidine-l-carboxylate (Intermediate B5; 2.87 g, 12.6 mmol) in THF (30 mL) was added 1 M lithium bis(trimethylsilyl)amide in THF (13.3 mL) over 20 min. The mixture was stirred for 1 h before the addition of trimethylsilyl chloride (1.74 mL, 13.7 mmol). After stirring at 0 0C for 30 min, the solution was cooled to -78 0C and bromine (0.645 mL, 12.6 mmol) was added. The mixture was allowed to reach r.t. and then poured into a solution of 10percent Na2S2O3 (20 mL) and saturated NH4Cl (20 mL). Extraction with EtOAc (2 x 80 mL) gave the title compound. Yield 3.69 g (96percent).
Reference: [1] Patent: WO2009/150144, 2009, A1, . Location in patent: Page/Page column 139
[2] Tetrahedron Letters, 2012, vol. 53, # 7, p. 852 - 853
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3419 - 3424
[4] Patent: WO2004/41279, 2004, A1, . Location in patent: Page/Page column 70
[5] Patent: WO2015/88565, 2015, A1, . Location in patent: Paragraph 00214
[6] Patent: WO2008/42925, 2008, A1,
  • 17
  • [ 206989-61-9 ]
  • [ 301221-79-4 ]
Reference: [1] Patent: US6248755, 2001, B1,
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