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Basic Information
| CAS No.: | 1289942-66-0 |
|---|---|
| Name: | N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine |
| Article Data: | 14 |
| Molecular Structure: | |
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|
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| Formula: | C12H15FN2O3 |
| Molecular Weight: | 254.261 |
| Synonyms: | N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine;Alanine, N-[3-fluoro-4-[(MethylaMino)carbonyl]phenyl]-2-Methyl-;5.N-[3-Fluoro-4-[(MethylaMino)carbonyl]phenyl]-2-Methylalanine;N-[3-Fluoro-4-[(MethylaMino)carbonyl]phenyl]-2-Methylalanine(for EnzalutaMide) |
| EINECS: | 807-437-3 |
| Density: | 1.286 |
| Boiling Point: | 455℃ |
| Flash Point: | 229℃ |
| PSA: | 81.92000 |
| LogP: | 2.10820 |
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Synthetic route
- 292621-45-5
2-fluoro-4-bromobenzamide
- 1289942-66-0
2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid
Conditions
| Conditions | Yield |
|---|---|
| With 2-acetylcyclohexanone; water; potassium carbonate; copper(l) chloride In N,N-dimethyl-formamide at 30 - 105℃; for 12h; | 89.1% |
- 749927-69-3
4-bromo-2-fluoro-N-methylbenzanamide
- 62-57-7
2-Aminoisobutyric acid
- 1289942-66-0
2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid
Conditions
| Conditions | Yield |
|---|---|
| With 2-acetylcyclohexanone; potassium carbonate; copper(l) chloride In N,N-dimethyl-formamide at 110℃; for 16h; | 88.7% |
| With water; potassium carbonate; L-proline; copper(l) chloride In N,N-dimethyl-formamide at 100℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; | 87% |
| Stage #1: 4-bromo-2-fluoro-N-methylbenzanamide; 2-Aminoisobutyric acid With potassium carbonate; copper(l) chloride In water; N,N-dimethyl-formamide at 30℃; Stage #2: With 2-acetylcyclohexanone In water; N,N-dimethyl-formamide at 105℃; Inert atmosphere; Stage #3: With citric acid In Isopropyl acetate; water pH=4; | 75.4% |
- 749927-69-3
4-bromo-2-fluoro-N-methylbenzanamide
- 15028-41-8
methyl 2-aminoisobutyrate hydrochloride
- 1289942-66-0
2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid
Conditions
| Conditions | Yield |
|---|---|
| With 2-acetylcyclohexanone; water; potassium carbonate; copper(l) chloride In N,N-dimethyl-formamide at 30 - 105℃; for 12h; | 87.3% |
- 292621-45-5
2-fluoro-4-bromobenzamide
- 60421-20-7
benzyl 2-amino-2-methylpropionate hydrochloride
- 1289942-66-0
2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid
Conditions
| Conditions | Yield |
|---|---|
| With copper(l) iodide; 2-acetylcyclohexanone; water; potassium carbonate In dimethyl sulfoxide at 40 - 110℃; for 10h; | 83.6% |
- 915087-25-1
2-fluoro-N-methyl-4-amino-benzamide
- 2052-01-9
2-bromo-2-methylpropionic acid
- 1289942-66-0
2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid
Conditions
| Conditions | Yield |
|---|---|
| With triethylamine In dichloromethane at 20℃; for 72h; | 76% |
| With triethylamine In dichloromethane at 20 - 30℃; for 15h; Inert atmosphere; | 12 g |
| With triethylamine In dichloromethane at 20 - 30℃; for 15h; Inert atmosphere; |
- 2052-01-9
2-bromo-2-methylpropionic acid
- 1289942-66-0
2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: 4-amino-2-fluoro-N-methylbenzamide hydrochloride With triethylamine In N,N-dimethyl acetamide at 70℃; for 1h; Stage #2: 2-bromo-2-methylpropionic acid In N,N-dimethyl acetamide at 100℃; for 1.66667h; | 53% |
- 112704-79-7
2-fluoro-4-bromobenzoic acid
- 1289942-66-0
2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1.1: thionyl chloride / N,N-dimethyl-formamide; Isopropyl acetate / 4.58 h / 21 - 72 °C / Inert atmosphere; Industry scale 2.1: water; Isopropyl acetate / 1.08 h / 2 - 35 °C / Inert atmosphere; Industry scale 3.1: potassium carbonate / copper(l) chloride / N,N-dimethyl-formamide; water / 30 °C 3.2: 105 °C / Inert atmosphere 3.3: pH 4 View Scheme | |
| Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 10 - 30 °C 2.1: water; tert-butyl methyl ether / 10 - 30 °C / pH 8 - 9 3.1: potassium carbonate / N,N-dimethyl-formamide; 1,4-dioxane; water / 0.33 h / Inert atmosphere 3.2: 24.33 h / Inert atmosphere; Reflux View Scheme | |
| Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; thionyl chloride / ethyl acetate / 4 h / 20 °C / Inert atmosphere; Reflux 2: ethyl acetate / 0.25 h / 30 - 35 °C 3: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 120 °C / Inert atmosphere View Scheme |
- 151982-51-3
4-bromo-2-fluorobenzoyl chloride
- 1289942-66-0
2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1.1: water; Isopropyl acetate / 1.08 h / 2 - 35 °C / Inert atmosphere; Industry scale 2.1: potassium carbonate / copper(l) chloride / N,N-dimethyl-formamide; water / 30 °C 2.2: 105 °C / Inert atmosphere 2.3: pH 4 View Scheme | |
| Multi-step reaction with 2 steps 1: ethyl acetate / 0.25 h / 30 - 35 °C 2: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 120 °C / Inert atmosphere View Scheme | |
| Multi-step reaction with 2 steps 1.1: toluene; N,N-dimethyl-formamide / 1 h / 10 - 15 °C 2.1: copper(l) chloride; N,N-dimethyl-aniline / N,N-dimethyl-formamide / 75 - 80 °C / Inert atmosphere 2.2: 75 - 80 °C / Inert atmosphere 2.3: 0.25 h / Inert atmosphere View Scheme |
- 403-24-7
2-fluoro-4-nitrobenzoic acid
- 1289942-66-0
2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; thionyl chloride / Isopropyl acetate / 60 °C / Inert atmosphere 2.1: Isopropyl acetate / 5 h / Inert atmosphere 3.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 50 °C / 4500.45 Torr / Autoclave 3.2: Heating 4.1: triethylamine / N,N-dimethyl acetamide / 1 h / 70 °C 4.2: 1.67 h / 100 °C View Scheme |
- 403-23-6
2-fluoro-4-nitrobenzoyl chloride
- 1289942-66-0
2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1.1: Isopropyl acetate / 5 h / Inert atmosphere 2.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 50 °C / 4500.45 Torr / Autoclave 2.2: Heating 3.1: triethylamine / N,N-dimethyl acetamide / 1 h / 70 °C 3.2: 1.67 h / 100 °C View Scheme |
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