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CAS No. : | 1183840-96-1 | MDL No. : | MFCD12149452 |
Formula : | C10H13FN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KVQQZPSWPXPGFE-UHFFFAOYSA-N |
M.W : | 180.22 | Pubchem ID : | 50989645 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H312-H315-H319-H332-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 |
---|---|---|
30% | Stage #1: bis(trichloromethyl) carbonate; 3-(1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazin-2-yl)aniline With sodium hydrogencarbonate In dichloromethane at 20℃; for 1h; Stage #2: 2-fluoro-6-(pyrrolidin-1-yl)aniline With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Reflux; | 5.5. 1-(3-(1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazin-2-yl)phenyl)-3-(2-fluoro-6-(pyrrolidin-1-yl)phenyl)urea (48) To a solution of 3-(1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-(7-tosyl-7H-pyrrolo[2,3-d] pyrimidin-4-yl)piperazin-2-yl)aniline 47 (0.82 g, 1.32 mmol, 1.0 eq) in CH2Cl2 (20 mL) was added a saturated solution of NaHCO3 (1 N, 10 mL) at rt, followed by the addition of triphosgene (1.20 g, 4.0 mmol, 3.0 eq). The reaction mixture was stirred at rt for 1 hr. The organic phase was separated and dried (Na2SO4). After filtration, 2-fluoro-6-(pyrrolidin-1-yl)aniline (0.72 g, 4.0 mmol,3.0 eq) and DIEA (0.81 g, 6.6 mmol, 5.0 eq) were added to the solution.The mixture was refluxed for 2 hr and then concentrated in vacuo to afford a residue that was purified by silica gel column (petroleum ether/EtOAc=2/1 (v/v)) to give 1-(3-(1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazin-2-yl)phenyl)-3- (2-fluoro-6-(pyrrolidin-1-yl)phenyl)urea 48 (0.32 g, 30%) as light yellow solid. 1H NMR (400 MHz, CDCl3) δ: 8.39 (s, 1H), 8.05 (d,J=8.0 Hz, 2H), 7.63 (s, 1H), 7.46 (d, J=4.0 Hz, 1H), 7.34 (s, 1H),7.29-7.27 (m, 3H), 7.19-7.09 (m, 2H), 6.71-6.68 (m, 2H), 6.52 (d,J=4.0 Hz, 1H), 4.65 (d, J=12.8 Hz, 1H), 4.40 (d, J=12.8 Hz, 1H),3.61-3.59 (m, 2H), 3.41-3.37 (m, 4H), 3.32-3.24 (m, 3H), 3.11-3.05(m, 1H), 2.63-2.58 (m, 1H), 2.48-2.42 (m, 1H), 2.38 (s, 3H), 2.18-2.11(m, 1H), 1.98-1.95 (m, 4H), 0.81 (s, 9H), -0.05 (s, 3H), -0.06 (s, 3H).13C NMR (400 MHz, CDCl3) δ: 160.1, 157.7, 156.5, 154.6, 152.9, 146.7,146.6, 145.4, 141.4, 139.0, 135.1, 129.7, 129.4, 128.2, 128.1, 128.0,122.8, 121.8, 119.2, 119.0, 114.0, 113.8, 111.9, 111.8, 106.5, 106.3,104.9, 104.8, 66.9, 61.5, 56.3, 53.3, 52.9, 50.2, 45.8, 29.7, 25.9, 25.2,21.7,18.3,5.3, 5.4; HR-ESI-MS (m/z): 812.3736, calcd for[M+H]+ C42H54FN8O4SSi: 813.3737. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.60 g | Stage #1: carbon disulfide; 2-fluoro-6-(pyrrolidin-1-yl)aniline With triethylamine In tetrahydrofuran at 20℃; for 1h; Stage #2: With di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran at 20℃; for 2h; Stage #3: With dmap In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / tetrahydrofuran / 1 h / 20 °C 1.2: 2 h / 20 °C 1.3: 20 °C 2.1: camphor-10-sulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 4 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iron; acetic acid In ethanol; water Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide / 120 °C 2: acetic acid; iron / ethanol; water / Reflux |