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CAS No. : | 1015474-32-4 | MDL No. : | MFCD29919294 |
Formula : | C14H14N4O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RSNPAKAFCAAMBH-UHFFFAOYSA-N |
M.W : | 286.29 | Pubchem ID : | 24967599 |
Synonyms : |
CC-122
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 80.87 |
TPSA : | 107.08 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.07 cm/s |
Log Po/w (iLOGP) : | 1.36 |
Log Po/w (XLOGP3) : | -0.03 |
Log Po/w (WLOGP) : | -0.11 |
Log Po/w (MLOGP) : | 0.49 |
Log Po/w (SILICOS-IT) : | 0.82 |
Consensus Log Po/w : | 0.51 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.88 |
Solubility : | 3.75 mg/ml ; 0.0131 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.77 |
Solubility : | 4.88 mg/ml ; 0.017 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.42 |
Solubility : | 0.109 mg/ml ; 0.000379 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.98 |
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 |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79.8% | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide | To a stirred mixture of 2-amino-6-nitrobenzoic acid (25-1) (1 g, 5.49 mmol) and imidazole (1.2eq.) in Acetonitrile (10 mL ) was added acetyl chloride (25-2) (469 µL, 6.58 mmol) and the reaction was stirred overnight.3-aminopiperidine-2,6-dione hydrochloride (903 mg, 5.49 mmol) was then added followed by rest of the base to make it total 1H-Imidazole (1.34 g, 19.7 mmol). Then phosphorous acid, triphenyl ester (1.72 mL, 6.58 mmol) was added and the reaction was refluxed for two days. After cooling to r.t.added 40 mL water, slowly form suspension, filter off, wash with water and EtOAc. Isolated solid 3-(2-methyl-5-nitro-4-oxoquinazolin-3(4H)- yl)piperidine-2,6-dione (1-2) (953 mg, 3.01 mmol, 55.0 percent) as a solid. LC/MS (ES+): m/z 317 [M + H]+ Brought 3-(2-methyl-5-nitro-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione (25-3) (690 mg, 2.18 mmol) up in 10 mL dry DMF, and added dihydroxypalladium (306 mg, 0.218 mmol) on carbon 50percent wet, purged with nitrogen for 15 min, purged with hydrogen three cycles and subjected to hydrogen 1 atm for overnight; Filtered off Pd via celite pad, concentrated and subject to purification by isco MeOH/DCM to give 3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)- yl)piperidine-2,6-dione (25-4) (498 mg, 1.73 mmol, 79.8 percent) as an off-white solid. LC/MS (ES+): m/z 287 [M + H]+ |
69% | With hydrogen In N,N-dimethyl-formamide for 12 h; | Step 5: A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidiπe- 2,6-dione (250 mg) and Pd(OH)2 on carbon (1 10 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hours. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3-(5-amino-2-methyl-4-oxo-4H- quinazolin-3-yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent yield): HPLC: Waters Symmetry C18, 5μm, 3.9 x 150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3PO4, 3.52 min (99.9percent); mp: 293-295 °C; 1H NMR (DMSO-d6) δ 2.10-2.17 (m, IH, CHH), 2.53 (s, 3η, CH3), 2.59- 2.69 (m, 2η, CH2), 2.76-2.89 (m, 1η, CηH), 5.14 (dd, J= 6, 11 Hz, IH5 NCH), 6.56 (d, J= 8 Hz, I H, Ar), 6.59 (d, /= 8 Hz, IH, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J= 8 Hz, IH, Ar), 10.98 (s, IH, NH); 13C NMR (DMSO-ds) 5 20.98, 23.14, 30.52, 55.92, 104.15, 1 10.48, 111.37, 134.92, 148.17, 150.55, 153.62, 162.59, 169.65, 172.57; LCMS: MH = 287; Anal. Calcd. for C14H14N4O3 + 0.3 H2O: C, 57.65; H, 5.05; N, 19.21. Found: C, 57.50; H, 4.73; N, 19.00. |
69% | With hydrogen In N,N-dimethyl-formamide for 12 h; | Step 5: A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione (250 mg) and Pd(OH)2 on carbon (110 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3-(5-amino-2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent yield): HPLC: Waters Symmetry C18, 5 μm, 3.9*150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3PO4, 3.52 min (99.9percent); mp: 293-295° C.; 1H NMR (DMSO-d6) δ 2.10-2.17 (m, 1H, CHH), 2.53 (s, 3H, CH3), 2.59-2.69 (m, 2H, CH2), 2.76-2.89 (m, 1H, CHH), 5.14 (dd, J=6, 11 Hz, 1H, NCH), 6.56 (d, J=8 Hz, 1H, Ar), 6.59 (d, J=8 Hz, 1H, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J=8 Hz, 1H, Ar), 10.98 (s, 1H, NH); 13C NMR (DMSO-d6) δ 20.98, 23.14, 30.52, 55.92, 104.15, 110.48, 111.37, 134.92, 148.17, 150.55, 153.62, 162.59, 169.65, 172.57; LCMS: MH=287; Anal. Calcd. for C14H14N4O3+0.3H2O: C, 57.65; H, 5.05; N, 19.21. Found: C, 57.50; 1-1, 4.73; N, 19.00. |
69% | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide for 12 h; | A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione (250 mg) and Pd(OH)2 on carbon (110 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3-(5-amino- 2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent> yield): HPLC: Waters Symmetry C18, 5μιη, 3.9 x 150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3P04, 3.52 min (99.9percent); mp: 293-295 °C; 1H NMR (DMSO-d6) δ 2.10-2.17 (m, 1H, CHH), 2.53 (s, 3H, C), 2.59-2.69 (m, 2H, C), 2.76-2.89 (m, 1H, CHH), 5.14 (dd, J= 6, 11 Hz, 1H, NCH), 6.56 (d, J= 8 Hz, 1H, Ar), 6.59 (d, J= 8 Hz, 1H, Ar), 7.02 (s, 2H, N), 7.36 (t, J= 8 Hz, 1H, Ar), 10.98 (s, 1H, NH); 13C NMR (DMSO-d6) δ 20.98, 23.14, 30.52, 55.92, 104.15, 110.48, 111.37, 134.92, 148.17, 150.55, 153.62, 162.59, 169.65, 172.57; LCMS: MH = 287; Anal. Calcd. for C14H14N403 + 0.3 H20: C, 57.65; H, 5.05; N, 19.21. Found: C, 57.50; H, 4.73; N, 19.00 |
69% | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide for 12 h; | Step 5: A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione (250 mg) and Pd(OH)2 on carbon (110 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3-(5-amino-2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent yield): HPLC: Waters Symmetry C18, 5μm, 3.9 x 150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3PO4, 3.52 min (99.9percent); mp: 293-295 °C; 1H NMR (DMSO-d6) δ 2.10-2.17 (m, 1H, CHH), 2.53 (s, 3H, CH3), 2.59-2.69 (m, 2H, CH2), 2.76-2.89 (m, 1H, CHH), 5.14 (dd, J = 6, 11 Hz, 1H, NCH), 6.56 (d, J = 8 Hz, 1H, Ar), 6.59 (d, J = 8 Hz, 1H, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J = 8 Hz, 1H, Ar), 10.98 (s, 1H, NH); 13C NMR (DMSO-d6) δ 20.98, 23.14. 30.52, 55.92, 104.15, 110.48, 111.37, 134.92, 148.17, 150.55, 153.62, 162.59, 169.65, 172.57; LCMS: MH = 287; Anal. Calcd. for C14H14N4O3 + 0.3 H2O: C, 57.65; H, 5.05; N, 19.21. Found: C, 57.50; H, 4.73; N, 19.00. |
69% | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide for 12 h; | A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione (250 mg) and Pd(OH)2 on carbon (110 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3-(5-amino-2-methyl-4-oxo- 4H-quinazolin-3-yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent yield): HPLC: Waters Symmetry C18, 5 m, 3.9 x 150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3PO4, 3.52 min (99.9percent); mp: 293-295 °C; 1H NMR (DMSO-d6) 2.10-2.17 (m, 1H, CHH), 2.53 (s, 3H, CH3), 2.59-2.69 (m, 2H, CH2), 2.76-2.89 (m, 1H, CHH), 5.14 (dd, J = 6, 11 Hz, 1H, NCH), 6.56 (d, J = 8 Hz, 1H, Ar), 6.59 (d, J = 8 Hz, 1H, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J = 8 Hz, 1H, Ar), 10.98 (s, 1H, NH); 13C NMR (DMSO-d6) 20.98, 23.14, 30.52, 55.92, 104.15, 110.48, 111.37, 134.92, 148.17, 150.55, 153.62, 162.59, 169.65, 172.57; LCMS: MH = 287; Anal. Calcd. for (0690) C14H14N4O3 + 0.3 H2O: C, 57.65; H, 5.05; N, 19.21. Found: C, 57.50; H, 4.73; N, 19.00. |
69% | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide for 12 h; | A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione (250 mg) and Pd(OH)2 on carbon (110 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3-(5-amino-2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent yield): HPLC: Waters Symmetry C18, 5 μm, 3.9*150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3PO4, 3.52 min (99.9percent); mp: 293-295° C.; 1H NMR (DMSO-d6) δ 2.10-2.17 (m, 1H, CHH), 2.53 (s, 3H, CH3), 2.59-2.69 (m, 2H, CH2), 2.76-2.89 (m, 1H, CHH), 5.14 (dd, J=6, 11 Hz, 1H, NCH), 6.56 (d, J=8 Hz, 1H, Ar), 6.59 (d, J=8 Hz, 1H, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J=8 Hz, 1H, Ar), 10.98 (s, 1H, NH); 13C NMR (DMSO-d6) δ 20.98, 23.14, 30.52, 55.92, 104.15, 110.48, 111.37, 134.92, 148.17, 150.55, 153.62, 162.59, 169.65, 172.57; LCMS: MH=287; Anal. Calcd. for C14H14N4O3+0.3H2O: C, 57.65; H, 5.05; N, 19.21. Found: C, 57.50; H, 4.73; N, 19.00. |
69% | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide for 12 h; | A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione (250 mg) and Pd(OH)2 on carbon (110 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3-(5-amino-2-methyl-4-oxo- 4H-quinazolin-3-yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent yield): HPLC: Waters (99.9percent); mp: 293-295 °C; 1H NMR (DMSO-d6) 2.10-2.17 (m, 1H, CHH), 2.53 (s, 3H, CH3), 2.59-2.69 (m, 2H, CH2), 2.76-2.89 (m, 1H, CHH), 5.14 (dd, J = 6, 11 Hz, 1H, NCH), 6.56 (d, J = 8 Hz, 1H, Ar), 6.59 (d, J = 8 Hz, 1H, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J = 8 Hz, 1H, Ar), 10.98 (s, 1H, NH); 13C NMR (DMSO-d6) 20.98, 23.14, 30.52, 55.92, 104.15, 110.48, 111.37, 134.92, 148.17, 150.55, 153.62, 162.59, 169.65, 172.57; LCMS: MH = 287; Anal. Calcd. for C14H14N4O3 + 0.3 H2O: C, 57.65; H, 5.05; N, 19.21. Found: C, 57.50; H, 4.73; N, 19.00. |
69% | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide for 12 h; | A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6- dione (250 mg) and Pd(OH)2on carbon (110 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3-(5-amino-2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent yield): HPLC: Waters Symmetry Ci8, 5μιη, 3.9 x 150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3P04, 3.52 min (99.9percent); mp: 293-295°C; 1H MR (DMSO-d6) δ 2.10-2.17 (m, 1H, CHH), 2.53 (s, 3H, CH3), 2.59-2.69 (m, 2H, CH2), 2.76-2.89 (m, 1H, CHH), 5.14 (dd, J= 6, 11 Hz, 1H, NCH), 6.56 (d, J= 8 Hz, 1H, Ar), 6.59 (d, J= 8 Hz, 1H, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J= 8 Hz, 1H, Ar), 10.98 (s, 1H, NH);13C MR (DMSO-d6) (5 20.98, 23.14, 30.52, 55.92, 104.15, 110.48, 111.37, 134.92, 148.17, 150.55, 153.62, 162.59, 169.65, 172.57; LCMS: ΜΗ = 287; Anal. Calcd. for Ci4Hi4N403+ 0.3 H20: C, 57.65; H, 5.05; N, 19.21. Found: C, 57.50; H, 4.73; N, 19.00. |
69% | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide for 12 h; | A mixture of 3 -(2-methyl-5-nitro-4-oxo-4H-quinazolin-3 -yl)-piperidine2,6-dione (250 mg) and Pd(OH)2 on carbon (110 mg) in DMF (40 mL) was shaken underhydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3 -(5-amino-2-methyl-4-oxo-4H-quinazolin-3 -yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent yield): HPLC: Waters Symmetry C,8, Sjim, 3.9 x 150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3P04, 3.52 mm (99.9percent); mp: 293-295 °C; ‘HNMR (DMSO-d6) (5 2.10-2.17 (m, 1H, CHJ]), 2.53 (s, 3H, CH3), 2.59-2.69 (m, 2H, CH2), 2.76-2.89 (m, 1H, CHJ]), 5.14 (dd, J 6, 11 Hz, 1H, NCR), 6.56 (d, J 8Hz, 1H, Ar), 6.59 (d, J= 8Hz, 1H, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J= 8 Hz, 1H, Ar), 10.98 (s, 1H, NI]); ‘3C NMR (DMSO-d6)(520.98,23.14,30.52, 55.92, 104.15, 110.48, 111.37, 134.92, 148.17, 150.55, 153.62,162.59, 169.65, 172.57; LCMS: MH = 287; Anal. Calcd. for C14H14N403 + 0.3 H20: C,57.65; H, 5.05; N, 19.21. Found: C, 57.50; H, 4.73; N, 19.00. |
69% | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide for 12 h; | A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6- dione (250 mg) and Pd(OH)2 on carbon (110 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3-(5-amino-2-methyl- 4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent yield): FIPLC: Waters Symmetry Ci8, 5μιη, 3.9 x 150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3P04, 3.52 min (99.9percent); mp: 293-295 °C; 1H MR (DMSO-d6) δ 2.10-2.17 (m, 1H, CHH), 2.53 (s, 3H, CH3), 2.59-2.69 (m, 2H, CH2), 2.76-2.89 (m, 1H, CHH), 5.14 (dd, J = 6, 11 Hz, 1H, NCH), 6.56 (d, J= 8 Hz, 1H, Ar), 6.59 (d, J= 8 Hz, 1H, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J= 8 Hz, 1H, Ar), 10.98 (s, 1H, NH); 13C MR (DMSO-d6) δ 20.98, 23.14, 30.52, 55.92, 104.15, 110.48, 111.37, 134.92, 148.17, 150.55, 153.62, 162.59, 169.65, 172.57; LCMS: ΜΗ = 287; Anal. Calcd. for Ci4Hi4N403 + 0.3 H20: C, 57.65; H, 5.05; N, 19.21. Found: C, 57.50; H, 4.73; N, 19.00. |
69% | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide for 12 h; | A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)- piperidine-2,6-dione (250 mg) and Pd(OH)2 on carbon (110 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3 -(5 -amino-2-methyl-4-oxo-4H-quinazolin-3 -yl)piperidine-2,6-dione as a white solid (156 mg, 69percent yield): HPLC: Waters Symmetry Cr8, Sjim, 3.9 x 150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3P04, 3.52 mm (99.9percent); mp: 293-295 °C; ‘HNMR(DMSO-d6)(52.10-2.17(m, 1H, CHJ]), 2.53 (s, 3H, CH3), 2.59-2.69 (m, 2H, CH2), 2.76-2.89 (m, 1H, CHJ]), 5.14 (dd, J= 6, 11Hz, 1H, NCR), 6.56 (d, J 8 Hz, 1H, Ar), 6.59 (d, J 8 Hz, 1H, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J = 8 Hz, 1H, Ar), 10.98 (s, 1H, NI]); ‘3C NIVIR (DMSO-d6) (520.98, 23.14, 30.52, 55.92, 104.15, 110.48, 111.37, 134.92, 148.17, 150.55, 153.62, 162.59, 169.65, 172.57; LCMS:I\’IH = 287; Anal. Calcd. for C14H14N403 + 0.3 H20: C, 57.65; H, 5.05; N, 19.21. Found:C, 57.50; H, 4.73; N, 19.00. |
156 mg | With 10 wt% Pd(OH)2 on carbon; hydrogen In N,N-dimethyl-formamide for 12 h; | A mixture of 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione (250 mg) and Pd(OH)2 on carbon (110 mg) in DMF (40 mL) was shaken under hydrogen (50 psi) for 12 hrs. The suspension was filtered through a pad of Celite and washed with DMF (10 mL). The filtrate was concentrated in vacuo and the resulting oil was purified by flash column chromatography (silica gel, methanol/methylene chloride) to give 3-(5-amino-2-methyl-4-oxo- 4H-quinazolin-3-yl)-piperidine-2,6-dione as a white solid (156 mg, 69percent yield): HPLC: Waters Symmetry Ci8, 5um, 3.9 x 150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1percent H3P04, 3.52 min (99.9percent); mp: 293-295 °C; 1H NMR (DMSO-d6) δ 2.10-2.17 (m, 1H, CHH), 2.53 (s, 3H, Ci), 2.59-2.69 (m, 2H, C), 2.76-2.89 (m, 1H, CHH), 5.14 (dd, J = 6, 11 Hz, 1H, NCH), 6.56 (d, J = 8 Hz, 1H, Ar), 6.59 (d, J = 8 Hz, 1H, Ar), 7.02 (s, 2H, NH2), 7.36 (t, J= 8 Hz, 1H, Ar), 10.98 (s, 1H, NH); 13C NMR (DMSO-d6) |
A1369052[ 1398053-45-6 ]
3-(5-Amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione hydrochloride
Reason: Free-salt
[ 1290541-46-6 ]
(E)-3-Benzyl-2-(2-(pyridin-3-yl)vinyl)quinazolin-4(3H)-one
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