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CAS No.: | 850140-72-6 |
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Name: | Afatinib |
Article Data: | 26 |
Molecular Structure: | |
Formula: | C24H25ClFN5O3 |
Molecular Weight: | 485.946 |
Synonyms: | BIBW 2992; |
Density: | 1.38g/cm3 |
Melting Point: | 100 - 102 °C |
Boiling Point: | 676.917°C at 760 mmHg |
Flash Point: | 363.186°C |
Appearance: | Off-White Solid |
PSA: | 88.61000 |
LogP: | 4.53590 |
afatinib
Conditions | Yield |
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Stage #1: (E)-4-(dimethylamino)-2-butenoic acid hydrochloride With thionyl chloride In 1-methyl-pyrrolidin-2-one at -5 - 0℃; for 0.333333h; Stage #2: 6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline In 1-methyl-pyrrolidin-2-one at -5 - 0℃; for 0.25h; | 95% |
With Bromoform; triethylamine; triphenylphosphine In dichloromethane at 25℃; for 1h; Reagent/catalyst; Temperature; | 93% |
Stage #1: (E)-4-(dimethylamino)-2-butenoic acid hydrochloride With thionyl chloride In 1-methyl-pyrrolidin-2-one; ethyl acetate at 5℃; Stage #2: 6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline In 1-methyl-pyrrolidin-2-one; ethyl acetate at 0℃; Temperature; | 87.4% |
Stage #1: (E)-4-(dimethylamino)-2-butenoic acid hydrochloride With thionyl chloride In N,N-dimethyl acetamide at -20 - -15℃; Stage #2: 6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline In N,N-dimethyl acetamide; water at -25 - -20℃; | 48 g |
Stage #1: (E)-4-(dimethylamino)-2-butenoic acid hydrochloride With thionyl chloride In N,N-dimethyl acetamide at -20 - -10℃; Stage #2: 6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline In N,N-dimethyl acetamide at -25 - -20℃; for 0.166667h; Stage #3: In water Alkaline conditions; |
dimethylaminoacetaldehyde-hydrogen sulphite adduct
afatinib
Conditions | Yield |
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Stage #1: (S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate With lithium chloride In ethanol at -5℃; Stage #2: dimethylaminoacetaldehyde-hydrogen sulphite adduct With potassium hydroxide In ethanol; water for 1h; | 91% |
afatinib
Conditions | Yield |
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With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Temperature; Solvent; | 87.3% |
(2E)-(N,N-dimethylamino)-2-butenoyl chloride
afatinib
Conditions | Yield |
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With piperidine In tetrahydrofuran at 5 - 40℃; for 9h; Temperature; Reagent/catalyst; Solvent; | 86.1% |
(E)-4-(dimethylamino)-2-butenoic acid methyl ester
afatinib
Conditions | Yield |
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Stage #1: 6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline With trimethylaluminum In hexane; dichloromethane at 20℃; for 2h; Stage #2: (E)-4-(dimethylamino)-2-butenoic acid methyl ester In hexane; dichloromethane at 60℃; for 5h; Solvent; | 98% |
Conditions | Yield |
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Stage #1: C26H31ClFN4O6P With lithium chloride; potassium hydroxide In ethanol; water at -5 - 10℃; for 2h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Stage #2: 2-dimethylamino-1-hydroxyethanesulfonic acid sodium salt In ethanol; water at 0 - 18℃; for 7h; Solvent; Reagent/catalyst; Temperature; | 91.7% |
Conditions | Yield |
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With potassium tert-butylate In tert-butyl alcohol at 50℃; for 1h; Reagent/catalyst; Solvent; | 89% |
Conditions | Yield |
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Stage #1: dimethylaminoacetaldehyde diethyl acetal With hydrogenchloride In water at 30 - 35℃; for 8.3h; Large scale; Stage #2: diethyl ((4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazoline-6-ylcarbamoyl)methyl)phosphonate With lithium chloride; potassium hydroxide In water at -7 - -5℃; for 2h; Large scale; | 78% |
trans-4-dimethylamino crotonic acid chloride hydrochloride salt
afatinib
Conditions | Yield |
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In tetrahydrofuran at 0 - 5℃; | 97.5% |
In 1-methyl-pyrrolidin-2-one; water at -5 - 0℃; for 0.5 - 0.75h; | 87% |
In 1-methyl-pyrrolidin-2-one at -5 - 0℃; | 14.1 g |
(S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate
afatinib
Conditions | Yield |
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With lithium chloride; potassium hydroxide In ethanol; water at -10℃; for 2h; | 60% |