Product Details of [ 7321-93-9 ]
| CAS No. : | 7321-93-9 | MDL No. : | MFCD00234054 |
| Formula : | C5H4Cl2N2 | Boiling Point : | 290.8°C at 760 mmHg |
| Linear Structure Formula : | - | InChI Key : | - |
| M.W : | 163.01 | Pubchem ID : | 595729 |
| Synonyms : |
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Computed Properties of [ 7321-93-9 ]
| TPSA :Topological Polar Surface Area |
38.9 |
H-Bond Acceptor Count : |
2 |
| XLogP3 : |
1.8 |
H-Bond Donor Count : |
1 |
| SP3 : |
0.00 |
Rotatable Bond Count : |
0 |
Application In Synthesis of [ 7321-93-9 ]
- Upstream synthesis route of [ 7321-93-9 ]
- Downstream synthetic route of [ 7321-93-9 ]
- 1
[ 70593-57-6 ]
[ 7321-93-9 ]
| Yield | Reaction Conditions | Operation in experiment |
| 73% |
With sodium hydroxide; water; bromine In 1,4-dioxane at 0 - 25℃; for 18.00 h; |
NaOH (6.60 g, 165 mmol) was dissolved in H2O (31 mL) and cooled in an ice bath.
Bromine (2.08 mL, 40.6 mmol) was added dropwise and the yellow solution was stirred for 15 min. 4,6-Dichloro-nicotinamide (7.27 g, 38.1 mmol) in 1,4-dioxane (21 mL) was added dropwise to the bromine solution over 30 min.
The reaction was allowed to warm slowly to 25° C. over 18 h.
The volatiles were removed in vacuo and the resultant solution was diluted with brine and poured into EtOAc.
The aqueous phase was separated and extracted twice with EtOAc.
The organic layers were combined, dried (Na2SO4), decanted and concentrated to afford an orange oil.
The resultant oil was purified on a 100 g SiO2 flash chromatography cartridge with 25 percent EtOAc-hexanes to afford 4,6-dichloro-pyridin-3-ylamine as a tan solid (4.54 g, 73percent).
30percent Aqueous H2O2 solution (29 mL) was cooled in an ice bath.
|
Reference：
[1] Patent: US2006/217417, 2006, A1. Location in patent: Page/Page column 13
| Yield | Reaction Conditions | Operation in experiment |
|
|
B. 4,6-Dichloro-3-pyridinamine STR366 To a solution of 172A (192 mg, 1.0 mmol) in 1.0 mL of dry DMF cooled at 0° C. was added triethylamine (0.14 mL, 1.0 mmol), followed by diphenylphosphoryl azide (0.216 mL, 1.0 mL). The mixture was stirred at ambient temperature for 1.0 hr and poured into a mixture of ice-water-EtOAc. The reaction mixture was extracted with EtOAc (x2) and combined extracts washed with water, sat'd NaHCO3, sat'd NaCl and dried over Na2 SO4. Concentration in vacuo gave 217 mg of light tan solid. Above solid was dissolved in 2.5 mL of dry toluene and heated to reflux. A solution of tert-butyl alcohol in 1.0 mL of dry toluene was added and the mixture was heated at 90-95° C. for 4.0 hrs. Concentration in vacuo followed by flash chromatography (hexane-EtOAc: 95:5) on silica gel gave 168 mg of colorless oil. Above material was treated with trifluoroacetic acid (1.5 mL) and CH2 Cl2 (0.5 mL). Concentrated in vacuo and residue was extracted with CH2 Cl2 (x2) and combined extracts washed with water, sat'd NaHCO3, sat'd NaCl and dried over Na2 SO4. Concentration in vacuo gave 104 mg of 172B as a white solid. |
- 2
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[ 7321-93-9 ]
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C21H20FN5OS
[ No CAS ]
- 3
-
[ 7321-93-9 ]
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4-(6-(7-fluoro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)thiazolo[4,5-c]pyridin-2-yl)morpholine
[ No CAS ]
- 4
-
[ 7321-93-9 ]
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C21H20FN5OS*ClH
[ No CAS ]
- 5
-
[ 7321-93-9 ]
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C10H10ClN3O2
[ No CAS ]
- 6
-
[ 7321-93-9 ]
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4-(6-chloro thiazolo[4,5-c]pyridin-2-yl) morpholine
[ No CAS ]
- 7
-
[ 7321-93-9 ]
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C6H2BrClN2S
[ No CAS ]
- 8
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[ 7321-93-9 ]
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[ 1244058-73-8 ]
- 9
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[ 7321-93-9 ]
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[ 1244058-72-7 ]
- 10
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[ 7321-93-9 ]
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[ 532-55-8 ]
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C13H9Cl2N3OS
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 87% |
In acetone; at 60℃; for 3h; |
A solution of commercially available [7321-93-9]4,6-dichloropyridin-3-amine (8.0 g, 49.07 mmol) and benzoyl isothiocyanate (7.3 ml_, 53.98 mmol) in acetone (120 ml_) was stirred at 60 C for 3 hours. The reaction was monitored by the TLC. The solvent was evaporated and the solid was filtered, washed with n-hexane (100 ml.) and dried to give the desired product as an off-white solid (14.0 g, 87%). (0683) MS: 328.0 (M+H)+. (0684) 1H-NMR (400 MHz, DMSO- 6) d =12.39 (s, 1 H), 12.02 (s, 1 H), 8.74 (s, 1 H), 7.98-7.99 (m, 3H), 7.67-7.68 (m, 1 H), 7.56 (t, J = 7.60 Hz, 2H). |
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