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850140-72-6

Basic Information
CAS No.: 850140-72-6
Name: Afatinib
Article Data: 26
Molecular Structure:
Molecular Structure of 850140-72-6 (Afatinib)
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
Synthetic route

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline

(E)-4-(dimethylamino)-2-butenoic acid hydrochloride

850140-72-6

afatinib

Conditions
ConditionsYield
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;
1413945-87-5

dimethylaminoacetaldehyde-hydrogen sulphite adduct

850140-72-6

afatinib

Conditions
ConditionsYield
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%

C36H36ClFN5O5P

850140-72-6

afatinib

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Temperature; Solvent;87.3%

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline

1056149-69-9

(2E)-(N,N-dimethylamino)-2-butenoyl chloride

850140-72-6

afatinib

Conditions
ConditionsYield
With piperidine In tetrahydrofuran at 5 - 40℃; for 9h; Temperature; Reagent/catalyst; Solvent;86.1%

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline

212776-19-7

(E)-4-(dimethylamino)-2-butenoic acid methyl ester

850140-72-6

afatinib

Conditions
ConditionsYield
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%

2-dimethylamino-1-hydroxyethanesulfonic acid sodium salt

C26H31ClFN4O6P

850140-72-6

afatinib

Conditions
ConditionsYield
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%

C20H18ClF2N5O

86087-23-2

(S)-3-hydroxytetyrahydrofurane

850140-72-6

afatinib

Conditions
ConditionsYield
With potassium tert-butylate In tert-butyl alcohol at 50℃; for 1h; Reagent/catalyst; Solvent;89%
3616-56-6

dimethylaminoacetaldehyde diethyl acetal

diethyl ((4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazoline-6-ylcarbamoyl)methyl)phosphonate

850140-72-6

afatinib

Conditions
ConditionsYield
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%

6-Amino-4-[(3-chloro-4-fluorophenyl)amino]-7-[(S)-(tetrahydrofuran-3-yl)oxy]quinazoline

1055943-40-2

trans-4-dimethylamino crotonic acid chloride hydrochloride salt

850140-72-6

afatinib

Conditions
ConditionsYield
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
618061-76-0

(S)-diethyl 2-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-ylamino)-2-oxoethylphosphonate

2-dimethylamino-1-hydroxyethanesulfonic acid sodium salt

850140-72-6

afatinib

Conditions
ConditionsYield
With lithium chloride; potassium hydroxide In ethanol; water at -10℃; for 2h;60%
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    Afatinib CAS No.:850140-72-6 Name: Afatinib Synonyms: BIBW 2992; Tovok; (2E)-N-[4-[(3-Chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-2-butenamide

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