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CAS No. :71233-25-5 MDL No. :MFCD09878815
Formula : C13H21NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :WCTXJAXKORIYNA-UHFFFAOYSA-N
M.W : 271.31 Pubchem ID :15852989
Synonyms :

Safety of [ 71233-25-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 71233-25-5 ]

* 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 [ 71233-25-5 ]
  • Downstream synthetic route of [ 71233-25-5 ]

[ 71233-25-5 ] Synthesis Path-Upstream   1~10

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YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen; sodium carbonate In ethanol at 50℃; for 48 h; Autoclave 1-tert-butyl 4-ethyl3-oxopiperidine-1,4-dicarboxylate (74)
A mixture of ethyl 1-benzyl-3-oxo-4-piperidinecarboxylate hydrochloride (10.0 g,33.58 mmol), Pd/C (10percent wt., 1.0 g), Boc20 (14.64g, 67.16 mmol), Na2C03 (3.56 g,33.58 mmol) and EtOH (100 ml)was loaded into a Parr autoclave. Hydrogen was10 introduced (38 bar), and the mixturewas stirred at 50 oc for 48 h. Afterthe autoclave was cooled to 25 oc the hydrogen pressurewas released, the catalyst was removed by filtration, and the mixture was concentrated under reduced pressureto give a yellow oil. Purification by column chromatography (hexane: EtOAc 2:1) gave the title compound(9.10 g, 100percent) as a clear oil.15Rf = 0.70 (hexane:EtOAc 2:1); 1H NMR (CDCI3,400 MHz) o 12.10 (s, 1H, enolform -OH),4.25 (q, J= 7.1 Hz, 2H), 4.04 (s, 2H), 3.50 (t, J= 5.8 Hz, 2H), 2.33 (t, J= 5.8 Hz, 2H),1.48 (s, 9H), 1.32 (t, J = 7.1 Hz, 3H); HRMS (CI) calc. for C13H21NOs (M+NH4)+ 289.1763, found: 289.1759.
94% With triethylamine In diethyl ether; ethanol EXAMPLE 33A
1-tert-butyl 4-ethyl 3-oxo-1,4-piperidinedicarboxylate
Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride (24.16 g, 81.1 mmol) in ethanol (250 mL) was treated with triethyl amine (11.3 mL, 81.1 mmol), di-tert-butyl dicarbonate (18.6 g, 85.3 mmol) and 10percent Pd/C (0.13 g).
After stirring under H2 (1 atm) at 50° C. for 1 hour, the mixture was allowed to cool to ambient temperature and filtered through diatomaceous earth with an ethanol (2*20 mL) rinse.
The filtrate was concentrated under reduced pressure.
The residue was treated with diethyl ether (200 mL) and refiltered with a diethyl ether rinse (2*30 mL).
The filtrate was concentrated under reduced pressure to provide the title compound as a yellow oil (20.6 g, 94percent yield).
1H NMR (CD3OD, 300 MHz) δ 1.32 (t, J=6.9 Hz, 3H), 1.48 (s, 9H), 2.32-2.26 (m, 3H), 3.5 (t, J=5.7 Hz, 1H), 4.0 (br s, 1H), 4.24 (q, J=6.9 Hz, 2H); MS (DCI/NH3) m/z 272 (M+H)+, 289 (M+NH4)+.
88%
Stage #1: With hydrogen In ethanol at 20℃; for 15 h;
Stage #2: With triethylamine In ethanol at 20℃; for 3 h;
Example 1 Preparation of Compound 1benzhydryl bromide,Cs2CO3Step A - Synthesis of Intermediate Compound IBA solution of starting material IA (5.0 g, 16.8 mmol) in ethanol (50 mL) and Pd/C (0.5 g, 10percent w/w) was hydrogenated at 1 atm for 15 hours at room temperature. (BOC)2O (4.0 g, 18.3 mmol) and triethylamine (2.6 mL, 18.6 mmol) were then added to the reaction mixture. The resulting solution was allowed to stir at room temperature for about 3 hours, then filtered through celite. The filtrate was concentrated in vacuo and the resulting residue was redissolved in CH2Cl2 and washed with water. The organic phase was collected, dried over Na2SO4 and concentrated in vacuo to provide IB as brown oil (4.0 g, 88percent).
83% With hydrogen; sodium hydrogencarbonate In ethanol; water at 20℃; for 48 h; Preparation 46; 1 -ferf-Butyl-4-ethyl-3-oxopiperidine-1 ,4-dicarboxylate; To a solution of ethyl-i-benzyl-S-oxopiperidine^-carboxylate hydrochloride (51.3 g, 170 mmol) in ethanol (200 mL) and water (200 mL) was added di-fe/f-butyl dicarbonate (40.8 g, 187 mmol), sodium hydrogen carbonate (14.3 g, 170 mmol), palladium on carbon (18.1 g, 17.0 mmol) and the reaction mixture was hydrogenated at room temperature at 10 Bar for 48 h. The mixture was filtered through Arbocel.(R). and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate and water, the aqueous phase was extracted with ethyl acetate and the combined organic solution was evaporated to give the title compound as a brown oil (44.1 g, 83percent). 1H NMR (300 MHz, CDCI3) δ 12.03 (s, 1 H), 4.22 (q, 2H), 4.05 (s, br, 2H), 3.49-3.50 (m, 2H), 2.35-2.36 (m, 2H), 1.46 (s, 9H), 1.30 (t, 3H); LC-MS (ESf): 270 [M-H].
72% With hydrogen; triethylamine In ethanol for 10 h; F.
3-Oxo-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (34a2)
To ethyl-N-benzyl-3-oxo-4-piperidinecarboxylate hydrochloride (25 g, 95.7 mmol) in EtOH was added di-t-butyl-dicarbonate (22.7 g, 105.2 mmol), triethylamine (16 mL, 114.8 mmol) and Pd(OH)2 (1.34 g).
The reaction mixture was hydrogenated under 60 psi hydrogen for 10 hours.
The reaction mixture was filtered and concentrated under reduced pressure, then diluted with EtOAc and washed with water, brine and sodium sulfate to provide a yellow oil (19 g, 72percent) MS (ES-): m/z=270 (M-1) 1H NMR (400 MHz, CHLOROFORM-D) δ=1.26 (t, J=7.14 Hz, 3H) 1.41 (s, 9H) 2.23-2.32 (m, 2H) 3.06 (d, J=7.33 Hz, 2H) 3.44 (t, J=5.75 Hz, 2H) 3.98 (s, 1H) 4.19 (q, J=7.07 Hz, 2H)

Reference: [1] Synthesis, 2011, # 8, p. 1208 - 1212
[2] Patent: WO2015/124941, 2015, A1, . Location in patent: Page/Page column 134
[3] Patent: US2002/19388, 2002, A1,
[4] Patent: WO2008/130581, 2008, A1, . Location in patent: Page/Page column 161; 171
[5] Patent: WO2007/15162, 2007, A1, . Location in patent: Page/Page column 85
[6] Patent: US2009/325948, 2009, A1, . Location in patent: Page/Page column 92
[7] Journal of Medicinal Chemistry, 2006, vol. 49, # 26, p. 7843 - 7853
[8] Patent: US5965578, 1999, A,
[9] Patent: US2005/65178, 2005, A1, . Location in patent: Page/Page column 20
[10] Patent: CN107188894, 2017, A, . Location in patent: Paragraph 0006; 0007; 0018
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YieldReaction ConditionsOperation in experiment
100%
Stage #1: With hydrogen In ethanol for 16 h;
Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16 h;
STEP A: l -Benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (5.0 g, 16.8 mmol) was stirred in dry ethanol (55 mL). The flask was evacuated and filled with nitrogen prior to the addition of 10percent Pd/C ( 1 .0 g). The resulting suspension was stirred for 16 hours under an atmosphere of hydrogen. The reaction mixture was filtered through Celite and concentrated to afford a yellow solid (2.9 g). This was immediately dissolved in CH2C12 (100 mL), treated with Boc-anhydride (4.4 g, 20.2 mmol) and DIPEA (4.3 g, 33.6 mmol), and stirred for 16 hours at room temperature. The organics were washed sequentially with HCI (IN), water and brine, dried over magnesium sulfate, filtered, and concentrated to afford 3-oxo-piperidine-l ,4-dicarboxylic acid 1 -te -butyl ester 4-ethyl ester as a clear oil (4.8 g, 100percent yield). MS (ESI) m/e (M+H+): 271.36
94.25% With hydrogen; triethylamine In ethanol for 24 h; A mixture of 1 -benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (1 1 .31 g, 38 mmol), di-t-butyl dicarbonate (8.78 g, 40.2 mmol), Et3N (5.4 ml_, 38.7 mmol) and Pd(OH)2 on carbon (20percent on dry basis-Pearlman's catalyst) (1 .3 g) were taken into EtOH (1 10 ml_). The mixture was hydrogenated at 60 psi for 24 h in a Parr bottle. The catalyst was removed by filtration and the filtrate was concentrated to dryness to tan solid. Crude residue was shaken well with hexane (100 ml_) and filtered. The filtrate was concentrated to yield the title compound (9.70 g, 94.25percent). MS (ESI) mass calcd. for Ci3H2i NO5, 271 .32; 1H NMR (400 MHz, CDCI3) 4.24 (q, J = 7.1 , 2H), 4.03 (s br, 2H), 3.49 (t, J = 5.6, 2H), 2.32 (m, 3H), 1 .47 (s, 9H), 1 .31 (t, J = 7.1 , 3H).
94.25% With hydrogen; triethylamine In ethanol for 24 h; Step A. 3-Oxo-piperidine-1 ,4-dicarboxylic acid 1 -tert-butyl ester 4-ethyl ester. A mixture of 1 -benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (1 1 .31 g, 38 mmol), di-t-butyl dicarbonate (8.78 g, 40.2 mmol), Et3N (5.4 ml_, 38.7 mmol) and Pd(OH)2 on carbon (20percent on dry basis-Pearlman's catalyst) (1 .3 g) were taken into EtOH (1 10 ml_). The mixture was hydrogenated at 60 psi for 24 h in a Parr bottle. The catalyst was removed by filtration and the filtrate was concentrated to dryness to tan solid. Crude residue was shaken well with hexane (100 ml_) and filtered. The filtrate was concentrated to yield the title compound (9.70 g, 94.25percent). MS (ESI) mass calcd. for Ci3H2i NO5, 271 .32; 1H NMR (400 MHz, CDCI3) 4.24 (q, J = 7.1 , 2H), 4.03 (s br, 2H), 3.49 (t, J = 5.6, 2H), 2.32 (m, 3H), 1 .47 (s, 9H), 1 .31 (t, J = 7.1 , 3H).
Reference: [1] Patent: WO2011/29842, 2011, A1, . Location in patent: Page/Page column 40
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[3] Patent: WO2015/124941, 2015, A1, . Location in patent: Page/Page column 133; 134
[4] Patent: WO2011/50200, 2011, A1, . Location in patent: Page/Page column 45
[5] Patent: WO2011/50202, 2011, A1, . Location in patent: Page/Page column 44
[6] Patent: US2005/101602, 2005, A1, . Location in patent: Page/Page column 26
[7] Patent: WO2011/103091, 2011, A1, . Location in patent: Page/Page column 88-89
[8] Patent: WO2013/185084, 2013, A1, . Location in patent: Paragraph 0102
  • 3
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  • [ 70637-75-1 ]
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YieldReaction ConditionsOperation in experiment
86%
Stage #1: With triethylamine In methanol for 1 h;
Stage #2: for 16 h;
[0084] Preparation of 1-tert-butyl 4-ethyl 3-oxopiperidine-l,4-dicarboxylate. Ethyl 3- oxopiperidine-4-carboxylate 2 (10.2 g, 60.0 mmol, 1.0 equiv) was dissolved in dry MeOH (200 mL), and Et3N (33.1 mL, 240 mmol, 4.0 equiv) was added. The mixture was stirred for 1 h and Boc20 (19.5 g, 90.0 mmol, 1.5 equiv) was added and stirred for 16 h. The solvent was concentrated in vacuo and the crude was purified by column chromatography (silica, petroleum ether/EtOAc =9: 1) to give 1-tert-butyl 4-ethyl 3-oxopiperidine-l,4-dicarboxylate 3 light yellow oil (11.5 g, yield: 86percent). ESI-MS (M+H-56) +: 216.0. 1H NMR (400 MHz, CDC13) δ: 4.24 (q, 2H), 4.03 (s, 2H), 3.49 (t, 2H), 2.33 (t, 2H), 1.47 (s, 9H), 1.31 (t, 3H).
65.6% With triethylamine In dichloromethane for 0.25 h; Cooling with ice-bath Di-te/t-butyl dicarbonate (3.19 g, 14.60 mmol) was added to a solution of ethyl 3- oxopiperidine-4-carboxylate (2.5 g, 14.60 mmol) and triethylamine (2.030 niL, 14.60 mmol) in DCM (50 niL) cooled on an ice-bath. One DMAP crystal was added and the suspension was stirred for 15 minutes. The solution was poured onto ice and neutralised with HCl (2M, aq). The organic layer was washed with HCl (0.1M), H2O, dried (MgSO4), filtered and concentrated to give 1-tert-butyl 4-ethyl 3-oxopiperidine-l,4-dicarboxylate (2.60 g, 65.6 percent). MS (ESI-) m/z 270
92% With triethylamine In methanol; water; ethyl acetate Part B
Preparation of ethyl 1-(t-butoxycarbonyl)-3-oxo-4-piperidinecarboxylate
In a dry flask, the crude ethyl 3-oxo-4-piperidine-carboxylate 2.88 g, 16.8 mmol) is dissolved in methanol (40 mL) and di-t-butyl dicarbonate (4.03 g, 18.5 mmol) and triethylamine (3.74 g, 36.9 mmol) were added.
The reaction mixture was stirred under an argon atmosphere for 6 hours at room temperature.
The reaction mixture was concentrated in vacuo and then water (30 mL) and ethyl acetate (30 mL) were added.
The aqueous layer was separated and then extracted twice with ethyl acetate (30 mL).
The combined organic extracts were dried with magnesium sulfate, filtered and concentrated in vacuo.
Purification by flash column chromatography (20percent ethyl acetate/hexanes) provided 4.19 g (92percent) of a colorless oil. 1H NMR (300 MHz, CDCl3), δ: 12.08 (bs, 1H), 4.23 (q, 2H, J=7), 4.03 (bs, 2H), 3.49 (t, 2H, J=6), 2.32 (bt, 2H, J=6), 1.47 (s, 9H), 1.31 (t, 3H, J=7).
Reference: [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[2] Patent: WO2013/185084, 2013, A1, . Location in patent: Paragraph 0084
[3] Patent: WO2010/53438, 2010, A1, . Location in patent: Page/Page column 58; 59
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S762-S764
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S254 - S256
[6] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 18, p. 4023 - 4028
[7] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4544 - 4567
[8] Patent: US2003/32654, 2003, A1,
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YieldReaction ConditionsOperation in experiment
93%
Stage #1: With potassium carbonate In dichloromethane; water at 20℃;
Stage #2: With N,N`-dimethylethylenediamine In dichloromethane at 20℃; for 1 h;
Palladium hydroxide on carbon (20percent, 2.9 g) and hydrochloric acid (2M, 50 mL) were added to a solution of (RS)-ethyl 3-oxo-1(phenylmethyl)piperidinecarboxylate hydrochloride (25 g, 83.95 mmol) in ethanol (320 mL) and the mixture was shaken under hydrogen (50 psi) overnight. The mixture was filtered through a glass fibre pad and the solvent was evaporated under reduced pressure. Dichloromethane (200 mL), aqueous potassium carbonate (20percent, 200 mL) and di-tert-butyl dicarbonate (25.65 g, 117.53 mmol) were added and the mixture was stirred at room temperature overnight. The layers were separated and N,N-dimethylethylenediamine (4.4 mL, 40 mmol) was added to the organic fraction. The mixture was stirred for at room temperature for 1 h, washed with aqueous citric acid (10percent, 3.x.200 mL), water (2.x.200 mL) and brine, dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound (21.8 g, 93percent). m/z (ES+) 216 (M+1-C4H8).
Reference: [1] Archiv der Pharmazie, 2010, vol. 343, # 3, p. 143 - 151
[2] Patent: US2003/236250, 2003, A1, . Location in patent: Page 32
[3] Tetrahedron Asymmetry, 2004, vol. 15, # 20, p. 3281 - 3287
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 6, p. 2421 - 2426
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YieldReaction ConditionsOperation in experiment
80% With potassium carbonate In tetrahydrofuran; water at 20℃; for 2 h; Step 2[00173] Methyl 4-methylpyridin-3-ylcarbamate: A solution of di-terz-butyl dicarbonate (5.66 g, 26 mmol), potassium carbonate (12 g, 86.4 mmol) and water (10OmL) was added to a solution of ethyl 3-oxopiperidine- 4-carboxylate acetic salt (15 g, 21.6 mmol) in tetrahydrofuran (400 mL). The resulting mixture was stirred at ambient temperature for about 2 hours. After removing the solvent in vacuo, standard extractive workup with ethyl acetate (3 x 200 mL) afforded the title product as a pale white solid (14 g; yield = 80percent). LC-MS: m/z = 172/272 (M+H)+.
Reference: [1] Patent: WO2010/123919, 2010, A2, . Location in patent: Page/Page column 60
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Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4544 - 4567
[2] Tetrahedron Asymmetry, 2004, vol. 15, # 20, p. 3281 - 3287
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, p. S254 - S256
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S762-S764
[5] Patent: WO2011/103091, 2011, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 18, p. 4023 - 4028
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[3] Patent: WO2013/185084, 2013, A1,
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  • [ 1053656-57-7 ]
Reference: [1] Patent: WO2011/29842, 2011, A1,
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
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  • [ 1142188-60-0 ]
YieldReaction ConditionsOperation in experiment
86.4% With sodium In ethanol at 70℃; for 5 h; Inert atmosphere To a solution of Na (4.24 g, 184 mmol, 4.37 mL, 2.50 eq) in EtOH (400 mL) was added 1 -tert- butyl 4-ethyl 3-oxopiperidine-l,4-dicarboxylate (20.0 g, 73.7 mmol, 1.00 eq) and acetic acid methanimidamide (11.5 g, 111 mmol, 1.50 eq) under N2. The mixture was stirred at 70 °C for 5 hours. The reaction mixture was adjusted to pH 7 with HCl (IN), extracted with DCM (3 x 200 mL), washed with brine (1 χ 400 mL), dried over Na2S04, filtered and concentrated under vacuum to give tert-butyl 4-hydroxy-6,8-dihydro-5H-pyrido [3,4-d]pyrimidine-7-carboxylate (16.0 g, 63.7 mmol, 86.4 percent yield) as a brown solid. ESI MS m/z 274.0 [M+H]+.
Reference: [1] Patent: WO2017/201161, 2017, A1, . Location in patent: Paragraph 0416
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YieldReaction ConditionsOperation in experiment
53% With sodium ethanolate In ethanolReflux; Inert atmosphere Intermediate 1, Step a: tert-Butyl 4-hydroxy-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate
To a solution of 1-tert-butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate (2.00 g, 7.39 mmol) in EtOH (37 mL) was added formamidine hydrochloride (910 mg, 11.08 mmol) followed by NaOEt (6.89 mL, 2.68 M in EtOH) dropwise.
The mixture was then heated to reflux overnight.
The mixture was concentrated in vacuo and then dissolved in a minimum amount of water.
The pH was adjusted to pH 7 with 1 N HCl.
The aqueous layer was then saturated with solid NaCl and extracted with a combination of EtOAc and DCM.
The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo.
Chromatography on SiO2 eluting with IPA/EtOAc afforded the desired product as a white solid (993 mg, 53percent). MS (ESI) mass calcd. C12H12N3O3, 251.13. m/z found 252.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.05 (s, 1H), 4.42 (s, 2H), 3.69-3.61 (m, 2H), 2.63 (s, 2H), 1.49 (s, 9H).
42% With sodium ethanolate In ethanol at 70℃; for 5 h; STEP B: 3-Oxo-piperidine- l ,4-dicarboxylic acid 1 -te -butyl ester 4-ethyl ester (4.6 g, 16.8 mmol) was dissolved in EtOH (90 mL), and sodium ethoxide (2.3 g, 33.6 mmol) and formamidine hydrochloride (2.0 g, 25.2 mmol) were sequentially added. The resulting suspension was heated to 70°C and stirred for 5 hours, and then the reaction mixture was cooled to room temperature and concentrated. The residue was dissolved in saturated ammonium chloride and extracted with ethyl acetate. The aqueous phase was adjusted to pH -5.5 using concentrated AcOH, and extracted several more times with ethyl acetate. The combined organic layers were sequentially washed with water and brine, dried, and concentrated to afford 4-hydroxy-5,8-dihydro-6H-pyrido[3,4- d]pyrimidine-7-carboxylic acid /er/-butyl ester as a brown solid (1.8 g, 42percent yield). MS (ESl) m/e (M+H+) = 251.28
Reference: [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[2] Patent: US2014/275120, 2014, A1, . Location in patent: Paragraph 0156
[3] Patent: WO2011/29842, 2011, A1, . Location in patent: Page/Page column 40
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