Product Details of [ 457097-93-7 ]
| CAS No. : | 457097-93-7 | MDL No. : | MFCD15527567 |
| Formula : | C9H8F3NO3 | Boiling Point : | - |
| Linear Structure Formula : | - | InChI Key : | - |
| M.W : | 235.16 | Pubchem ID : | 53419671 |
| Synonyms : |
|
Computed Properties of [ 457097-93-7 ]
| TPSA :Topological Polar Surface Area |
61.6 |
H-Bond Acceptor Count : |
7 |
| XLogP3 : |
2.3 |
H-Bond Donor Count : |
1 |
| SP3 : |
0.22 |
Rotatable Bond Count : |
3 |
Safety of [ 457097-93-7 ]
Application In Synthesis of [ 457097-93-7 ]
- Upstream synthesis route of [ 457097-93-7 ]
- Downstream synthetic route of [ 457097-93-7 ]
- 1
[ 175278-22-5 ]
[ 67-56-1 ]
[ 457097-93-7 ]
| Yield | Reaction Conditions | Operation in experiment |
| 96.2% |
Stage #1: at -5 - -4℃; for 1.00 h;
Stage #2: at 15 - 30℃; for 72.00 h; |
Thionyl chloride (2.68g, 0.023 mol) was added dropwise to methanol (12 mL) at -5° C via a syringe keeping the temperature at or below -4° C. The resulting mixture was stirred at or below -5° C for 1 hr., then 4-amino- 3-(trifluoromethoxy)benzoic acid (0.5g, 0.003 mol) [Alfa Aesar] was added in one portion. The reaction mixture was stirred at ambient temperature for 3 days after which the mixture was concentrated in vacuo. Water (10 mL) was added to the residue and sodium bicarbonate (0.46g, 5.4 mmol) was added in one portion and the mixture was stirred at ambient temperature for 30 min. The mixture was extracted several times with ethyl acetate. The combined organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to give 1.02g (96.2percent) of methyl 4-amino-3-(trifiuoromethoxy)berrzoate as a red oil that slowly sodified to a brown solid on cooling. MS: m/z 236.1 (MH+). 1H NMR (500 MHz, DMSO-d6): δ 3.771 (s, 3H), 6.329 (s, 2H), 6.834 (d, 1H), 7.6181 (s, 1H), 7.655 (dd, 1H). |
| 95% |
With hydrogenchloride In 1,4-dioxane at 20℃; for 72.00 h; |
A.
Methyl 4-amino-3-(trifluoromethoxy)benzoate
A mixture of 4-amino-3-(trifluoromethoxy)benzoic acid (8.88 g 40.2 mmol), MeOH (142 mL) and hydrochloric acid in 1,4-dioxane (4.0 M, 142 mL, 568 mmol) was stirred at room temperature for 72 h.
After removal of the organic solvent the pH of the residue was adjusted to pH 8 and the aqueous layer was extracted with ethyl acetate (50 mL*3).
The combined organic layers were dried and concentrated under vacuum to afford the title compound (9.3 g, 39.6 mmol, 95percent yield). MS (ESI) m/z 236.1 [M+1]+. |
Reference：
[1] Patent: WO2014/165816, 2014, A1. Location in patent: Page/Page column 92
[2] Patent: US2015/175557, 2015, A1. Location in patent: Paragraph 0300
[3] Patent: EP2017263, 2009, A1. Location in patent: Page/Page column 213
[4] Patent: US2013/115194, 2013, A1. Location in patent: Paragraph 0335
[5] Patent: US2013/287731, 2013, A1. Location in patent: Paragraph 0284; 0285
- 1
-
[ 457097-93-7 ]
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N-[4-({7-Methyl-8-[(3S)-3-methylpiperazin-1-yl]-5-oxo-1,5-dihydro-2H-chromeno[3,4-c]pyridin-3(4H)-yl}carbonyl)-2-(trifluoromethoxy)phenyl]methanesulfonamide hydrochloride
[ No CAS ]
- 2
-
[ 457097-93-7 ]
-
N-[4-{[7-methyl-5-oxo-8-(3,3,4-trimethylpiperazin-1-yl)-1,5-dihydro-2H-chromeno[3,4-c]pyridin-3(4H)-yl]carbonyl}-2-(trifluoromethoxy)phenyl]methanesulfonamide
[ No CAS ]
- 3
-
[ 457097-93-7 ]
-
N-[4-({8-[(3 S)-3-ethyl-4-methylpiperazin-1-yl]-7-methyl-5-oxo-1,5-dihydro-2H-chromeno[3,4-c]pyridin-3 (4H)-yl}carbonyl)-2-(trifluoromethoxy)phenyl]methanesulfonamide
[ No CAS ]
- 4
-
[ 457097-93-7 ]
-
N-[4-({8-[(3S)-3,4-dimethylpiperazin-1-yl]-7,10-dimethyl-5-oxo-1,5-dihydro-2H-chromeno[3,4-c]pyridin-3(4H)-yl}carbonyl)-2-(trifluoromethoxy)phenyl]ethanesulfonamide
[ No CAS ]
- 5
-
[ 457097-93-7 ]
-
N-[4-({8-[(3 S)-3,4-dimethylpiperazin-1-yl]-7-methyl-5-oxo-1,5-dihydro-2H-chromeno[3,4-c]pyridin-3 (4H)-yl}carbonyl)-2-(trifluoromethoxy)phenyl] ethanesulfonamide
[ No CAS ]
- 6
-
[ 457097-93-7 ]
-
N-[4-({8-[(3S)-3,4-dimethylpiperazin-1-yl]-7,10-dimethyl-5-oxo-1,5-dihydro-2H-chromeno[3,4-c]pyridin-3(4H)-yl}carbonyl)-2-(trifluoromethoxy)phenyl]methanesulfonamide
[ No CAS ]
- 7
-
[ 457097-93-7 ]
-
[ 7732-18-5 ]
-
[ 144-55-8 ]
-
[ 124-63-0 ]
-
4-[(methylsulfonyl)amino]-3-(trifluoromethoxy)benzoic acid
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With hydrogenchloride; sodium hydroxide; triethylamine; |
[Step 1] 4-[(Methylsulfonyl)amino]-3-(trifluoromethoxy)benzoic acid To a solution of <strong>[457097-93-7]methyl 4-amino-3-(trifluoromethoxy)benzoate</strong> (600 mg) in chloroform (20 ml), triethylamine (2.12 ml) and methanesulfonyl chloride (0.795 ml) were added dropwise under ice-cooling. The reaction solution was stirred at 0 C. for 10 minutes and at room temperature for 2 hours. Saturated sodium bicarbonate water was added thereto, and the reaction solution was stirred at room temperature for 20 minutes and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (20 ml). A 1 N aqueous solution of sodium hydroxide (20.4 ml) was added and the resultant reaction solution was stirred at 70 C. for one hour while heating. After the temperature of the solution was returned to room temperature and the reaction solution was concentrated up to about half under reduced pressure, 5 N hydrochloric acid (4 ml) was added dropwise. The precipitated solid was collected by filtration and dried under reduced pressure to obtain the title compound (740 mg) as a solid. 1H-NMR (DMSO-D6) delta: 3.17 (3H, s), 7.70 (1H, d, J=8.5 Hz), 7.81-7.84 (1H, m), 7.93 (1H, dd, J=8.9, 2.1 Hz), 10.25 (1H, s), 13.31 (1H, s). MS (ESI/APCI) m/z: 298 [M-1]- |
- 8
-
[ 457097-93-7 ]
-
[ 594-44-5 ]
-
4-[(ethylsulfonyl)amino]-3-(trifluoromethoxy)benzoic acid
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
|
[Step 1] 4-[(Ethylsulfonyl)amino]-3-(trifluoromethoxy)benzoic acid Using <strong>[457097-93-7]methyl 4-amino-3-(trifluoromethoxy)benzoate</strong> (300 mg) and ethanesulfonyl chloride (0.724 ml), synthesis was carried out in the same manner as in Step 1 of Example 8 to obtain the title compound (408 mg) as a solid. 1H-NMR (DMSO-D6) delta: 1.25 (3H, t, J=7.3 Hz), 3.27 (2H, q, J=7.3 Hz), 7.69 (1H, d, J=9.2 Hz), 7.80-7.84 (1H, m), 7.91 (1H, dd, J=8.5, 1.8 Hz), 10.27 (1H, s), 13.31 (1H, br s). MS (ESI/APCI) m/z: 312 [M-H]- |
- 9
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[ 457097-93-7 ]
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2-[(1R,3R,5S)-3-[(5-cyclopropyl-3-[4-methoxybicyclo[2.2.2]octan-1-yl]-1,2-oxazol-4-yl)carbonyloxy]-8-azabicyclo[3.2.1]octan-8-yl]-4-(trifluoromethoxy)-1,3-benzothiazole-6-carboxylic acid
[ No CAS ]
- 10
-
[ 457097-93-7 ]
-
methyl 2-[(1R,3R,5S)-3-[(5-cyclopropyl-3-[4-methoxybicyclo[2.2.2]octan-1-yl]-1,2-oxazol-4-yl)carbonyloxy]-8-azabicyclo[3.2.1]octan-8-yl]-4-(trifluoromethoxy)-1,3-benzothiazole-6-carboxylate
[ No CAS ]
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