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CAS No. : | 1187929-21-0 | MDL No. : | MFCD11506160 |
Formula : | C7H14ClNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YLONGJCTTJXALT-UHFFFAOYSA-N |
M.W : | 195.64 | Pubchem ID : | 50998249 |
Synonyms : |
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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 |
---|---|---|
15% | With triethylamine In 1-methyl-pyrrolidin-2-one at 160℃; for 3h; Microwave irradiation; | Methyl 2- 4- [5 -(3- [2-(difluoromethoxy)phenyllmethyH -2-methylimidazo [1 ,2-alpyridin-6-yl)pyrimidin-2-yllmorpholin-3-yH acetate Intermediate 29 (150 mg, 0.37 mmol), methyl 2-(morpholin-3-yl)acetate hydrochloride (125 mg, 0.64 mmol) and triethylamine (0.26 mL, 1.87 mmol) were suspended in 1 -methyl-2-pyrrolidinone (3 mL) and the reaction mixture was heated for atotal of 3 h at 160°C under microwave irradiation. The reaction mixture was allowed to cool to room temperature, then diluted with DCM (20 mL) and saturated aqueous sodium bicarbonate solution (10 mL). The organic phase was separated, washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified by5 preparative HPLC (Method C) to afford the title compound (50 mg, 15%) as a brown oil.oH (500 MHz, CD3OD) 8.50 (s, 2H), 8.13 (s, 1H), 7.52 (d, J9.3 Hz, 1H), 7.43 (d, J9.3Hz, 1H), 7.27 (t, J7.7 Hz, 1H), 7.19 (d, J8.2 Hz, 1H), 7.12 (t, J7.5 Hz, 1H), 7.07-6.75(m, 2H), 5.04 (d, J5.9 Hz, 1H), 4.41 (d, J 13.7 Hz, 1H), 4.37 (s, 2H), 3.96 (dd, J 11.4, 3.5Hz, 1H), 3.91 (d, J 11.8 Hz, 1H), 3.66 (dd, J 11.8, 2.9 Hz, 1H), 3.56 (s, 3H), 3.53 (dd, J 10 11.6, 3.0 Hz, 1H), 3.25 (td, J 13.1, 3.7 Hz, 1H), 2.88 (dd, J 15.0, 8.5 Hz, 1H), 2.64 (dd, J15.0, 6.1 Hz, 1H), 2.43 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With triethylamine In methanol at 20℃; | 1 Step 1: Synthesis of intermediate 1-37.1 Step 1: Synthesis of intermediate 1-37.1 To methyl 2-morpholin-3-ylacetate hydrochloride (1 g, 5.11 mmol) in methanol (25 mL) are added TEA (0.785 mL, 5.63 mmol) and acrylic acid methyl ester (0.465 mL, 5.16 mmol) and stirred overnight at r.t.. Again acrylic acid methyl ester (0.465 mL, 5.16 mmol) is added and stirred 3 days at r.t.. The reaction mixture is concentrated and the crude product is purified over silica gel (eluent: ethyl acetate). Yield 93%, m/z 246[M+H]+, rt 0.77 min, LC-MS Method V011_S01. |
68.6% | With triethylamine In methanol at 20℃; for 24h; | 88 Methyl 3 -[3 -(2-methoxy-2-oxoethyl)morpholin-4-yl]propanoate A mixture of methyl 2-(morpholin-3-yl)acetate hydrochloride (2 g, 10.2 mmol), methyl prop-2-enoate (1.389 ml, 15.31 mmol) and triethylamine (2.85 ml, 20.4 mmol) in methanol (50 ml) was stirred for 24 hours at ambient temperature. Solvent was removed in vacuo and the residue was dissolved in dichloromethane (10 ml), washed with brine, dried and concentrated to yield the diester (1.72 g, 68.6%), which was used directly in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With triethylamine; In N,N-dimethyl-formamide; at 80℃; for 7h;Sealed tube; | A vial was charged with <strong>[1064783-29-4]5-chloro-3-fluoro-2-nitropyridine</strong> (1 equiv), methyl 2-(morpholin-3-yl)acetate hydrochloride (1.1 equiv), DMF (0.4 M), and triethylamine (3 equiv). The vial was sealed and heated to 80 C for 7 h. The mixture was cooled, then diluted with 1N aq. HC1 and extracted with EtOAc (3x). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was dissolved in acetic acid (0.2 M). Iron (10 equiv) was added, and the resulting mixture was heated to 110 C overnight. The mixture was cooled to room temperature, diluted with EtOAc and filtered through celite. The filter pad was washed successively with EtOAc, DCM, and 20% MeOHIDCM. The combined filtrate was concentrated. The residue was suspended between sat. aq. sodium bicarbonate and EtOAc. The layers were separated, and the aq. layer was extracted with EtOAc (4x). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-90% EtOAc/heptane) to give l0-chloro-4,4a,5,7-tetrahydro- 1H-[ 1 ,4]oxazino[4,3 -d]pyrido[2,3 -b] [1 ,4]diazepin-6(2H)-one (54% yield) as awhite solid. ?HNMR (400 MHz, DMSO-d6) ppm 10.12 (s, 1 H) 8.05 (d, J=2.20 Hz, 1H)7.57(d,J=2.2OHz, 1H)3.75-3.88(m,2H)3.36-3.53(m,3H)3.16-3.29(m, 1H)2.96 (br d, J=ll.13 Hz, 1 H) 2.60-2.69 (m, 1 H) 2.02 (d, J=13.69 Hz, 1 H). LCMS (m/z)(M+H) = 254.0, Rt = 0.89 mm. |
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