Alternatived Products of [ 55899-42-8 ]
Product Details of [ 55899-42-8 ]
| CAS No. : | 55899-42-8 |
MDL No. : | MFCD07324817 |
| Formula : |
C9H14N2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : | 150.22 |
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 55899-42-8 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 55899-42-8 ]
* 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.
- Upstream synthesis route of [ 55899-42-8 ]
- Downstream synthetic route of [ 55899-42-8 ]
- 1
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[ 506-68-3 ]
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[ 55899-42-8 ]
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[ 57667-50-2 ]
- 2
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[ 25118-59-6 ]
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[ 55899-42-8 ]
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[ 1072930-35-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 71% |
|
2-(4-Bromo-3-chloro-phenyl)-1-propyl-1H-benzoimidazole A mixture of <strong>[25118-59-6]4-bromo-3-chloro-benzoic acid</strong> (10 g, 41.2 mmol) and N-propyl-benzene-1,2-diamine (7.43 g, 49.5 mmol) in PPA (100 ml) was heated to 150 C. for 18 h. The mixture was poured onto ice/water. The pH was adjusted to 10 with a 30% aq. soln. of NaOH, filtered and extracted twice with EtOAc. The combined org layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (Hex/EtOAc 100:0 to 30:70) provided the desired product (10.17 g, 71%). HPLC (System 3, 30-100% CH3CN): tR=2.263 min, MS (LC-MS): 350 [M+1]. |
| 71% |
With PPA; Polyphosphoric acid (PPA); at 150℃; for 18h; |
2-(4-Bromo-3-chloro-phenyl)-1 -propyl-1 H-benzoimidazoleA mixture of <strong>[25118-59-6]4-bromo-3-chloro-benzoic acid</strong> (10 g, 41.2 mmol) and N-propyl-benzene-1 ,2- diamine (7.43 g, 49.5 mmol) in PPA (100 ml) was heated to 150 0C for 18 h. The mixture was poured onto ice/water. The pH was adjusted to 10 with a 30% aq. soln. of NaOH, filtered and extracted twice with EtOAc. The combined org layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (Hex/EtOAc 100:0 to 30:70) provided the desired product (10.17 g, 71 %). HPLC (System 3, 30-100% CH3CN): tR = 2.263 min, MS (LC-MS): 350 [M+1]. |
- 3
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[ 855531-21-4 ]
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[ 55899-42-8 ]
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[ 1072930-70-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 4% |
Stage #1: 2-(4-chloro-phenylamino)-thiazole-5-carboxylic acid; N-propylbenzene-1,2-diamine With PPA (polyphosphoric acid) at 210℃; for 0.333333h; Microwave irradiation;
Stage #2: With sodium hydroxide In water |
112 (4-Chloro-phenyl)-[5-(1-propyl-1H-benzoimidazol-2-yl)-thiazol-2-yl]-amine
EXAMPLE 112 (4-Chloro-phenyl)-[5-(1-propyl-1H-benzoimidazol-2-yl)-thiazol-2-yl]-amine A mixture of 2-(4-Chlorophenylamino)-5-thiazolecarboxylic acid (300 mg, 1.18 mmol) and N-propyl-benzene-1,2-diamine (212 mg, 1.41 mmol) in PPA (5 ml) was heated to 210° C. in a microwave oven for 20 min. The mixture was then poured onto water and the pH of the solution was adjusted to 10 with an aq. soln. of 2N NaOH, and the mixture was extracted with DCM. The combined org. layers were dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (DCM/MeOH 100:0 to 94:6) afforded the desired product (16 mg, 4%). HPLC (System 2, 10-100% CH3CN): tR=3.270 min, MS (LC-MS): 369 [M+1]. |
| 4% |
With PPA; Polyphosphoric acid (PPA) at 210℃; for 0.333333h; Microwave irradiation; |
112
Example 112: (4-Chloro-phenyl)-[5-(1 -propyl-1 H-benzoimidazol-2-yl)-thiazol-2-yl]-amine A mixture of 2-(4-Chlorophenylamino)-5-thiazolecarboxylic acid (300 mg, 1.18 mmol) and N-propyl-benzene-1 ,2-diamine (212 mg, 1.41 mmol) in PPA (5 ml) was heated to 210 0C in a microwave oven for 20 min. The mixture was then poured onto water and the pH of the solution was adjusted to 10 with an aq. soln. of 2N NaOH, and the mixture was extracted with DCM. The combined org. layers were dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (DCIWMeOH 100:0 to 94:6) afforded the desired product (16 mg, 4%). HPLC (System 2, 10-100% CH3CN): tR = 3.270 min, MS (LC-MS): 369 [M+1]. |
- 4
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[ 55899-42-8 ]
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[ 110099-99-5 ]
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[ 1072930-24-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 11% |
In tetrahydrofuran at 20℃; for 1h; |
89
2-(2-Chloro-pyrimidin-5-yl)-1-propyl-1H-benzoimidazole A suspension of 2-hydroxy-pyrimidine-5-carboxylic acid (300 mg, 2.14 mmol) [J. Arukwe, K. Undheim, Acta. Chem. Scand. (1986) B40, 764-767], in POCl3 (20 ml) was heated to 80° C. for 16 h. The excess of POCl3 was evaporated and the residue was dried in HV for 2 h. The crude product was then taken up in anhydrous THF (30 ml), treated with N-propyl-benzene-1,2-diamine (354 mg, 2.36 mmol) and the solution was stirred for 1 h at RT. The mixture was then concentrated in vacuo. Purification by flash chromatography (100:0 to 75:25) afforded 2-(2-chloro-pyrimidin-5-yl)-1-propyl-1H-benzoimidazole (63 mg, 11%). UPLC (5-100% CH3CN): tR=0.974 min, MS (ES+): 273 [M+1]. |
- 5
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[ 55899-42-8 ]
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[ 56059-30-4 ]
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C15H15FN4O2
[ No CAS ]
- 6
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[ 25118-59-6 ]
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[ 55899-42-8 ]
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[ 1072930-34-7 ]
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