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Chemical Structure| 135072-13-8 Chemical Structure| 135072-13-8

Structure of 135072-13-8

Chemical Structure| 135072-13-8

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Product Details of [ 135072-13-8 ]

CAS No. :135072-13-8
Formula : C5H10N2O2
M.W : 130.15
SMILES Code : O=C(C1CNCCO1)N
English Name :Morpholine-2-carboxamide
MDL No. :MFCD15209643
InChI Key :LSNOAQQZECGQNS-UHFFFAOYSA-N
Pubchem ID :15955786

Safety of [ 135072-13-8 ]

Application In Synthesis of [ 135072-13-8 ]

* 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.

  • Downstream synthetic route of [ 135072-13-8 ]

[ 135072-13-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 110-91-8 ]
  • [ 135072-13-8 ]
YieldReaction ConditionsOperation in experiment
53% 21 EXAMPLE 21 EXAMPLE 21 As described in Example 20, but using a20% strength ethanolic solution of morpholine instead of an aqueous solution at a temperature of 25° C., morpholine-carboxamide was obtained in a yield of 53% of theory. 1 H-NMR: 3.29 (t,J=4.7 Hz, N-CH2); 3.57 (t,J=4.7 Hz, --0--CH2); 6.16 (O=C-NH2). 13 C-NMR 47.9 (--N--CH2 --); 70.0 (--0--CH2 --), 162.5 (C=O)
  • 2
  • [ 135072-13-8 ]
  • [ 350-46-9 ]
  • [ 1797906-03-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; 314 1-fluoro-4-nitrobenzene (0.75 ml, 7.09 mmol), morpholine-2-carboxamide (1535.03 mg, 9.21 mmol), potassium carbonate (4897.44 mg, 35.44 mmol) in N-Methyl-2-pyrrolidone (11 ml) was stirred at 100° C. for 3 overnights. The reaction was diluted with ethyl acetate, washed with water, dried and concentrated. The crude was washed with ethyl acetate, filtered and dried to provide 4-(4-nitrophenyl)morpholine-2-carboxamide. LCMS-ESI+ (m/z): [M+H]+ calcd for C11H13N3O4: 251.2. found: 252.1
  • 3
  • [ 135072-13-8 ]
  • [ 1214993-72-2 ]
  • [ 2168559-44-0 ]
YieldReaction ConditionsOperation in experiment
0.77 g With caesium carbonate In dimethyl sulfoxide at 80℃; for 8h; Inert atmosphere; 98.1 Step 1[0270j: To a solution of 4,6-dichloro-2-(3,5-dimethyl-1H-pyrazol-1- yl)pyrimidine [0241j (ig, 4.11 mmol) and morpholine-2-carboxamide [0269j (0.53g, 4.11 mmol) in dimethylsulfoxide (8 mL) was added cesium carbonate (2.68g, 8.22 mmol) under N2 atmosphere. The resultant reaction mixture was heated at 80 °C in a closed vial for 8 h, quenched with water and extracted with ethyl acetate (2x200 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford as a yellow gum and which was purified by column chromatography using 5% methanol in chloroform as eluent to afford 4-(6-chloro-2-(3,5- dimethyl- 1 H-pyrazol- 1 -yl)pyrimidin-4-yl)morpholine-2-carboxamide [0270j as an off-white solid (0.77 g), MS(M+1)+=337.
  • 4
  • [ 135072-13-8 ]
  • [ 2903406-80-2 ]
  • [ 2907674-40-0 ]
YieldReaction ConditionsOperation in experiment
With 2,4-dimethoxytoluene; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl acetamide; water at 20℃; 76 4-(4-(2-(Difluoromethyl)morpholino)-8-fluoro-2-(((2R,7aS)-2-fluorotetrahydro-1H-pyrrolizin-7a(5H)-yl)methoxy)pyrido[4,3-d]pyrimidin-7-yl)-5-ethyl-6-fluoronaphthalen-2-ol (Example 75) 7-(8-Ethyl-7-fluoro-3-hydroxynaphthalen-1-yl)-8-fluoro-2-(((2R,7aS)-2-fluorotetrahydro-1H-pyrrolizin-7a(5H)-yl)methoxy)pyrido[4,3-d]pyrimidin-4-ol (20 mg, 0.04 mmol, Intermediate B) was dissolved in N,N-dimethylacetamide (0.50 mL). HATU (60 mg, 0.16 mmol, Combi-Blocks Inc.), DIPEA (25 mg, 34 L, 0.20 mmol, Sigma-Aldrich Corporation), 2,4-dimethoxytoluene (12 mg, 12 L, 0.08 mmol, Aurum Pharmatech LLC) and 2-(difluoromethyl)morpholin-4-ium chloride (11 mg, 0.06 mmol, Enamine) were added and the mixture was stirred at rt overnight. Water (0.5 mL) was then added and the mixture was stirred overnight. The crude reaction mixture was purified with 0.1% formic acid in H2O and MeCN as mobile phase, XSelect column (19 x 100mm, 5 um), MS mode: ESI+ to yield 4-(4-(2-(difluoromethyl)morpholino)-8-fluoro-2-(((2R,7aS)-2-fluorotetrahydro-1H-pyrrolizin-7a(5H)-yl)methoxy)pyrido[4,3-d]pyrimidin-7-yl)-5-ethyl-6-fluoronaphthalen-2-ol (5.3 mg, 7.8 μmol, 20% yield) as formate. m/z (ESI): 630.2 (M+H)+.1H NMR (500 MHz, DMSO-d6) δ ppm 9.95 (s, 1 H), 9.24 (s, 1 H), 7.77 (dd, J=6.4, 3.1 Hz, 2 H), 7.34 (d, J=2.8 Hz, 3 H), 7.00 - 7.03 (m, 1 H), 7.01 (d, J=2.3 Hz, 1 H), 6.10 - 6.37 (m, 1 H), 5.45 - 5.65 (m, 1 H), 4.42 - 4.69 (m, 5 H), 4.06 - 4.17 (m, 3 H), 3.52 - 3.90 (m, 5 H), 2.01 - 2.39 (m, 7 H), 0.71 - 0.75 (m, 4 H).
 

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[ 135072-13-8 ]

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Related Parent Nucleus of
[ 135072-13-8 ]

Morpholines

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