Alternatived Products of [ 2923-94-6 ]
Alternatived Products of [ 2923-94-6 ]
Product Details of [ 2923-94-6 ]
| CAS No. : | 2923-94-6 |
MDL No. : | MFCD11845132 |
| Formula : |
C7H4FNO2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | N/A |
| M.W : | 153.11 g/mol |
Pubchem ID : | - |
| Synonyms : |
|
Application In Synthesis of [ 2923-94-6 ]
- Downstream synthetic route of [ 2923-94-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Erhitzen auf Temperaturen oberhalb des Schmelzpunkts; |
|
- 2
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[ 2923-94-6 ]
-
[ 107-08-4 ]
-
[ 134815-22-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 75% |
In N,N-dimethyl-formamide |
18.c c.
c. 6-fluoro-3-n-propyl-1,3-benzoxazolin-2(3H)-one To 670 mg (16.74 mmol) of hexanes washed sodium hydride in 20 ml DMF was added a solution of 2.33 g (15.22 mmol) 6-fluoro-1,3-benzoxazolin-2(3H)-one in 40 ml DMF. The reaction was stirred for 10 minutes before 3.11 g (18.3 mmol) 1-iodopropane was added and then stirred for 3 hr at room temperature. After pouring into 50 ml of ice/water, the aqueous phase was extracted with EtOAc (2*100 ml). The combined organic layers were washed with water (1*100 ml), dried over Na2 SO4 and evaporated to dryness in vacuo to give 2.2 g (75% yield) of the alkylated product as a brown solid. |
| 75% |
In N,N-dimethyl-formamide |
31.c c.
c. 6-fluoro-3-n-propyl-1,3-benzoxazolin-2(3H)-one To 670 mg (16.74 mmol) of hexanes washed sodium hydride in 20 ml DMF was added a solution of 2.33 g (15.22 mmol) 6-fluoro-1,3-benzoxazolin-2(3H)-one in 40 ml DMF. The reaction was stirred for 10 minutes before 3.11 g (18.3 mmol) 1-iodopropane was added and then stirred for 3 hr at room temperature. After quenching onto 50 ml of ice/water, the aqueous phase was extracted with EtOAc (2*100 ml). The combined organic layers were washed with water (1*100 ml), dried over Na2 SO4 and evaporated to dryness in vacuo to give 2.2 g (75% yield) of the alkylated product as a brown solid. |
- 3
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[ 75-44-5 ]
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[ 53981-24-1 ]
-
[ 2923-94-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 96% |
With potassium carbonate In dichloromethane; toluene |
18.b b.
b. 6-fluoro-1,3-benzoxazolin-2(3H)-one To 5.0 g (39.3 mmol) 2-amino-5-fluorophenol in 150 ml of CH2 Cl2 at 0° C. was added 13.4 (98 mmol) of potassium carbonate and 23 g (47 mmol) of 20 wt % phosgene in toluene. After warming to room temperature, the reaction was stirred an additional hour before pouring into 200 ml ice/water. The layers were separated and the aqueous phase was extracted with EtOAc (1*100 ml) before the organics were combined and dried over Na2 SO4. The solvent was removed in vacuo to give 5.76 g (96% yield) of the desired product as determined by 1 H NMR. |
| 96% |
With potassium carbonate In dichloromethane; toluene |
31.b b.
b. 6-fluoro-1,3-benzoxazolin-2(3H)-one To 5.0 g (39.3 mmol) 2-amino-5-fluorophenol in 150 ml of CH2 Cl2 at 0° C. was added 13.4 (98 mmol) of potassium carbonate and 23 g (47 mmol) of 20 wt. % phosgene in toluene. After warming to room temperature, the reaction was stirred an additional hour before quenching onto 200 ml ice/water. The layers were separated and the aqueous phase was extracted with EtOAc (1*100 ml) before the organics were combined and dried over Na2 SO4. The solvent was removed in vacuo to give 5.76 g (96% yield) of the desired product as determined by 1 H NMR. |
- 4
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[ 2923-94-6 ]
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6-fluoro-5-nitrobenzo[d]oxazol-2(3H)-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 92% |
With sulfuric acid; nitric acid at 0℃; for 2h; |
|
|
With nitric acid In sulfuric acid |
8 Production of the compound (III) from the compound (VIII):
EXAMPLE 8 Production of the compound (III) from the compound (VIII): A solution of 6-fluoro-2(3H)-benzoxazolone (1.0 g) in 80% aqueous sulfuric acid (6.5 g) was cooled to 0° to 5° C., and 60% nitric acid (0.8 g) was gradually added thereto at 0° to 5° C. The resultant mixture was stirred at the same temperature for 30 minutes and poured onto ice water. The precipitated crystals were collected by filtration, washed with water and dried to give 6-fluoro-5-nitro-2(3H)-benzoxazolone (1.1 g). m.p., 175.4° C. 1 H-NMR (CDCl3 +DMSO-D6) δ ppm: 4.0 (1H, broad), 6.8-7.9 (3H, m). |
Reference：
[1]Zhang, Hao; Liu, Kechang; Liu, Ruiquan; Li, Qibo; Li, Yongqiang; Wang, Qingmin; Liu, Shangzhong
[Chinese Journal of Chemistry, 2015, vol. 33, # 7, p. 749 - 755]
[2]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - US4640707, 1987, A
| Yield | Reaction Conditions | Operation in experiment |
|
|
3.43 3.43 6-Fluoro-3H-benzooxazol-2-one (86KK20j)
3.43 6-Fluoro-3H-benzooxazol-2-one (86KK20j) 4-Fluoro-2-hydroxyanilin (0.154 g, 1.21 mmol) and carbonyldiimidazole (0.250 g, 1.54 mmol) were reacted according to GP6 to give the crude title compound (86KK20j). |
- 6
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[ 2923-94-6 ]
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[ 637022-56-1 ]
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6-fluoro-3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-3H-benzooxazol-2-one
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 60℃; |
13
In a 4 mL vial was added 2-chloro-l-[4-(4-chloro-3-methoxy-phenyl)-piperazin-l- yl]-ethanone (1) (59 mg, 0.20 mmol, 1.0 equiv), 6-fluoro-3H-benzooxazol-2-one (30 mg, 0.20 mmol, 1.00 equiv), K2CO3 (110 mg, 0.80 mmol, 4.0 equiv) and 800 ?L of NMP. A stir bar was placed in the vial and the vial was then capped. The resultant mixture stirred at 60 0C overnight. The crude product was purified by reversed phase HPLC (acetonitrile -H2O with 0.1 % TFA as the eluent) to yield 6-fluoro-3-{2-[4-(4-chloro-3-methoxy-phenyl)- piperazin-l-yl]-2-oxo-ethyl}-3H-benzooxazol-2-one (18): HPLC retention time, 2.35 minutes (Agilent Zorbax SB-Cl 8, 2.1X50 mm, 5?, 35 0C) using 1 rnl/min flow rate, a 2.5 minute gradient of 20 % to 100 % B with a 1.1 minute wash at 100 % B (A = 0.1 % formic acid / 5 % acetonitrile / 94.9 % water, B = 0.1 % formic acid / 5 % water/ 94.9 % acetonitrile); MS (ES) M+H expected, 419.8, found, 419.9. |
- 7
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[ 2923-94-6 ]
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[ 874-98-6 ]
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[ 1246928-47-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 3h; |
|
Reference：
[1]Location in patent: scheme or table
Hare, Alissa A.; Leng, Lin; Gandavadi, Sunilkumar; Du, Xin; Cournia, Zoe; Bucala, Richard; Jorgensen, William L.
[Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5811 - 5814]
- 8
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[ 53981-24-1 ]
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[ 7693-46-1 ]
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[ 2923-94-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With triethylamine In dichloromethane at 20℃; for 1h; |
|
Reference：
[1]Location in patent: scheme or table
Hare, Alissa A.; Leng, Lin; Gandavadi, Sunilkumar; Du, Xin; Cournia, Zoe; Bucala, Richard; Jorgensen, William L.
[Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5811 - 5814]
- 9
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[ 201230-82-2 ]
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[ 53981-24-1 ]
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[ 2923-94-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 96 %Chromat. |
With oxygen In 1,2-dimethoxyethane at 110℃; for 4h; |
|
- 10
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[ 1481-27-2 ]
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[ 2923-94-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 57% |
With sodium azide; iodine; sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 2h; |
|
- 11
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[ 19213-72-0 ]
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[ 53981-24-1 ]
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[ 2923-94-6 ]
- 12
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[ 2923-94-6 ]
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[ 77725-08-7 ]
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6-fluoro-2-oxo-N-(4-phenylbutyl)-1,3-benzoxazole-3-carboxamide
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 79% |
Stage #1: 6-fluoro-3H-benzooxazol-2-one With pyridine; dmap at 20℃; for 0.5h; Inert atmosphere;
Stage #2: (4-isocyanatobutyl)benzene for 15h; Inert atmosphere; |
|
Reference：
[1]Bach, Anders; Pizzirani, Daniela; Realini, Natalia; Vozella, Valentina; Russo, Debora; Penna, Ilaria; Melzig, Laurin; Scarpelli, Rita; Piomelli, Daniele
[Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9258 - 9272]
- 13
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[ 53981-24-1 ]
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[ 530-62-1 ]
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[ 2923-94-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 91% |
In N,N-dimethyl-formamide at 0 - 60℃; for 4h; |
26.1 Step 1: 6-fluorobenzo[d]oxazol-2(3H)-one (26B)
Dissolve 26A (10g, 78.67 mmol) in anhydrous DMF (130 mL) and add N,N'-carbonyldimidazole (15.31 g, 94.40 mmol) dmf (100 mL) solution dropwise under the ice bath, add up, 60 °C reaction for 4 h. Cooled to room temperature, 600mL of water was added, extracted with EA (100mL X 4), backwashed with saturated saline combined with the organic layer, dried anhydrous sodium sulfate, and the residue was separated and purified by silica gel column chromatography after concentration (PE:EA(v/v) = 3:1) to give title compound 26B (11g, 91%). |
|
In N,N-dimethyl-formamide at 60℃; for 2h; |
|
Reference：
[1]Current Patent Assignee: HAISCO PHARMACEUTICAL GROUP CO., LTD. - WO2022/42591, 2022, A1
Location in patent: Paragraph 72-73
[2]Bach, Anders; Pizzirani, Daniela; Realini, Natalia; Vozella, Valentina; Russo, Debora; Penna, Ilaria; Melzig, Laurin; Scarpelli, Rita; Piomelli, Daniele
[Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9258 - 9272]
- 14
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[ 32315-10-9 ]
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[ 53981-24-1 ]
-
[ 2923-94-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 70% |
With pyridine In tetrahydrofuran at 5 - 20℃; for 3.5h; |
|
Reference：
[1]Zhang, Hao; Liu, Kechang; Liu, Ruiquan; Li, Qibo; Li, Yongqiang; Wang, Qingmin; Liu, Shangzhong
[Chinese Journal of Chemistry, 2015, vol. 33, # 7, p. 749 - 755]
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