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CAS No. : | 635713-68-7 | MDL No. : | MFCD11045505 |
Formula : | C12H15N3O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | CFLDCJYCZAHJCK-UHFFFAOYSA-N |
M.W : | 217.27 | Pubchem ID : | 49760350 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
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* 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% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In dichloromethane; for 12h; | EXAMPLE 32; (S)-4-chloro-7-(2-oxo-2-(2'-oxo-2',3'-dihydro-1'H-spiro/piperidine-4,4'-quinazoline]-1-yl)ethyl)-9-(2,2,2-trifluoroethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one; To a solution of (S)-2-(4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetic acid (50 mg, 0.133 mmol) in dichloromethane (25 mL) was added <strong>[635713-68-7]1'H-spiro[piperidine-4,4'-quinazolin]-2'(3'H)-one</strong> (31 mg, 0.14 mmol) followed by 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (47 mg, 0.15 mmol) and triethylamine (1.0 mL). After 12 h, the reaction mixture was washed with aqueous NaHCO3 followed by 1.0 M HCl and dried (Na2SO4). The solvent was removed and the crude product was purified by flash chromatography using 7% MeOH in dichloromethane to give (S)-4-chloro-7-(2-oxo-2-(2'-oxo-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinazoline]-2'(3'H)-1-yl)ethyl)-9-(2,2,2-trifluoroethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one (61 mg, 79%) as a white powder. MS (ESI) 575 (M+H); Rf=2.133. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In methanol; water; under 3102.97 Torr; for 48h; | To a solution of [1-BENZYL-2',] [3'-DIHYDRO-2'-OXOSPIRO- [PIPERIDINE-4, 4' (L'H)-] quinazoline (1.00 g) in degassed methanol (50 ml) and 6N hydrochloric acid (2.0 ml) was added 10% palladized charcoal (150 mg). The mixture was shaken on a Parr apparatus under an atmosphere of hydrogen at 60 psi overnight. LC/MS showed incomplete reaction. More 10% palladized charcoal (200 mg) was added, and the mixture was shaken for 2 more days. At that point, all starting material was consumed. The mixture was filtered and the filtrate concentrated to give 531 mg of the desired compound (64%). Mass spec.: 218. 12 (MH) [+.] |
64% | With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In methanol; water; under 3102.97 Torr; | To a solution of 1-benzyl-2',3'-dihydro-2'-oxospiro-[piperidine-4,4'(1'H)-quinazoline (1.00 g) in degassed methanol (50 ml) and 6N hydrochloric acid (2.0 ml) was added 10% palladized charcoal (150 mg). The mixture was shaken on a Parr apparatus under an atmosphere of hydrogen at 60 psi overnight. LC/MS showed incomplete reaction. More 10% palladized charcoal (200 mg) was added, and the mixture was shaken for 2 more days. At that point, all starting material was consumed. The mixture was filtered and the filtrate concentrated to give 531 mg of the desired compound (64%). Mass spec.: 218.12 (MH)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 2h; | General working method 1 (GMW1) for reacting (6-chloro-pyrimidin-4-yl)-(2,3-dihydro-indol-1-yl)-methanone with amine derivatives:0.41 mmol of an amine derivative were added to 100 mg (0.39 mmol) of (6-chloro-pyrimidin-4-yl)-(2,3-dihydro-indol-1-yl)-methanone and in the case of AA1 [A] 100 muL (0.58 mmol) DIPEA and in the case of AA1 [B] 150 muL (0.87 mmol) DIPEA in 10 mL DMF. The reaction mixture was stirred for 2 h at RT. The reaction mixture was evaporated down using the rotary evaporator and the residue was mixed with 20 mL water and stirred for 30 min at RT. The product precipitated was suction filtered, stirred with diisopropylether and isopropanol, suction filtered again and dried. Amine derivative [amount of amine Example derivative] Analytical Method Structure Yield data Example 2: GWM1 [A] 1'H-spiro[piperi- dine-4,4'-quinazo- lin]-2'(3'H)-one 90 mg (0.41 mmol) 150 mg (88% of theory)ESI-MS: m/z = 441 [M + H]+ Rf: 0.54 eluant A |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; | Example 14-methyl-6-(6-(2'-oxo-2',3'-dihydro-1'H-spiro[piperidin-4,4'-quinazolin]-1-yl)pyrimidine-4-carbonyl)benzo[d]oxazol-2(3H)-one; 144 mg (0.500 mmol) 6-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one, 108 mg (0.500 mmol) <strong>[635713-68-7]1'H-spiro[piperidin-4,4'-quinazolin]-2'(3'H)-one</strong> and 0.174 mL (1.00 mmol) DIPEA were combined in 5.0 mL DMF and stirred overnight at RT. The reaction mixture was purified by preparative HPLC, the fractions containing the product were combined and the organic solvent was eliminated i.vac. The aqueous phase was neutralised by the addition of 4N aqueous NaOH solution. The product precipitated as a solid was filtered off, washed with water and dried.Yield: 130 mg (55% of theoretical)ESI-MS: m/z=471 (M+H)+ Rt (HPLC)=2.55 min (Method C) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 48h; | Example 33,4-dimethyl-6-(6-(2'-oxo-2',3'-dihydro-1'H-spiro[piperidin-4,4'-quinazolin]-1-yl)pyrimidin-4-carbonyl)benzo[d]oxazol-2(3H)-one; 87.0 mg (0.400 mmol) <strong>[635713-68-7]1'H-spiro[piperidin-4,4'-quinazolin]-2'(3'H)-one</strong>, 122 mg (0.400 mmol) 6-(6-chloropyrimidin-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one and 0.140 mL (0.800 mmol) DIPEA were combined in 3.0 mL DMF and stirred for 48 h at RT. The reaction mixture was diluted with MeOH, the precipitate was suction filtered, washed with diethyl ether and dried.Yield: 184 mg (95% of theoretical)ESI-MS: m/z=485 (M+H)+ Rt (HPLC): 1.14 min (method A) |
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