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1421373-65-0

Basic Information
CAS No.: 1421373-65-0
Name: AZD-9291
Article Data: 37
Cas Database
Molecular Structure:
Molecular Structure of 1421373-65-0 (AZD-9291)
Formula: N/A
Molecular Weight: 499.616
Synonyms: AZD-9291;N(2{[2(diMethylaMino)ethyl](Methyl)aMino}4Methoxy5{[4(1Methyl1Hindol3yl)pyriMidin2yl]aMino}phenyl)prop2enaMide;N-[2-[[2-(Dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl]amino]phenyl]-2-propenamide;AZD9291,AZD-9291;2-Propenamide, N-[2-[[2-(dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl]amino]phenyl]-;AZD9291 N-[2-[[2-(Dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl]amino]phenyl]-2-propenamide;N-[2-[[2-(Dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl]amino]phenyl]-2-propenamide AZD9291;N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxy-5-((4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)amino)phenyl)acrylamide
EINECS: N/A
Density: 1.19±0.1 g/cm3(Predicted)
Melting Point: N/A
Boiling Point: N/A
Flash Point: N/A
Solubility: N/A
Appearance: N/A
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 0.00000
LogP: 0.00000
Synthetic route
1421372-66-8

N‑2‑[[2‑(dimethylamino)ethyl]methylamino]‑4‑methoxy‑5‑[[4‑(1‑methyl‑1H‑indole-3-yl)-2-pyrimidinyl]amino]aniline

79-10-7

acrylic acid

1421373-65-0

[N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide]

Conditions
ConditionsYield
In isopropyl alcohol at 35℃; for 4h; Temperature; Time; Solvent; Molecular sieve; Microwave irradiation;97.9%
In isopropyl alcohol at 35℃; for 4h; Solvent; Temperature; Molecular sieve; Microwave irradiation;97.9%
In ethanol; Petroleum ether at 55 - 60℃; for 8h; Time; Reflux; Molecular sieve;95.3%
Stage #1: acrylic acid With lithium carbonate; methanesulfonyl chloride In acetonitrile at 10℃; for 1.5h;
Stage #2: N‑2‑[[2‑(dimethylamino)ethyl]methylamino]‑4‑methoxy‑5‑[[4‑(1‑methyl‑1H‑indole-3-yl)-2-pyrimidinyl]amino]aniline In acetonitrile at 0℃; Reagent/catalyst; Solvent; Temperature;
92.2%
1421372-66-8

N‑2‑[[2‑(dimethylamino)ethyl]methylamino]‑4‑methoxy‑5‑[[4‑(1‑methyl‑1H‑indole-3-yl)-2-pyrimidinyl]amino]aniline

814-68-6

acryloyl chloride

1421373-65-0

[N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide]

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at -5℃; for 2h; Temperature; Solvent;95.5%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 40℃; for 12h; Solvent; Reagent/catalyst; Temperature;88%
With triethylamine In ethyl acetate at 5 - 10℃; Inert atmosphere;86.37%
1421372-66-8

N‑2‑[[2‑(dimethylamino)ethyl]methylamino]‑4‑methoxy‑5‑[[4‑(1‑methyl‑1H‑indole-3-yl)-2-pyrimidinyl]amino]aniline

625-36-5

2-chloropropionyl chloride

1421373-65-0

[N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide]

Conditions
ConditionsYield
Stage #1: N‑2‑[[2‑(dimethylamino)ethyl]methylamino]‑4‑methoxy‑5‑[[4‑(1‑methyl‑1H‑indole-3-yl)-2-pyrimidinyl]amino]aniline; 2-chloropropionyl chloride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water at 0 - 20℃; for 0.25h;
Stage #2: With sodium hydroxide In tetrahydrofuran; water at 65℃; for 10h;
94%
Stage #1: N‑2‑[[2‑(dimethylamino)ethyl]methylamino]‑4‑methoxy‑5‑[[4‑(1‑methyl‑1H‑indole-3-yl)-2-pyrimidinyl]amino]aniline; 2-chloropropionyl chloride In tetrahydrofuran; water at 20℃; for 0.25h;
Stage #2: With sodium hydroxide In tetrahydrofuran; water at 65℃; for 10h;
94%
Stage #1: N‑2‑[[2‑(dimethylamino)ethyl]methylamino]‑4‑methoxy‑5‑[[4‑(1‑methyl‑1H‑indole-3-yl)-2-pyrimidinyl]amino]aniline; 2-chloropropionyl chloride In tetrahydrofuran at 0 - 20℃; for 0.25h;
Stage #2: With sodium hydroxide In tetrahydrofuran at 65℃; for 10h;
94%
Stage #1: N‑2‑[[2‑(dimethylamino)ethyl]methylamino]‑4‑methoxy‑5‑[[4‑(1‑methyl‑1H‑indole-3-yl)-2-pyrimidinyl]amino]aniline; 2-chloropropionyl chloride In tetrahydrofuran; water at 0 - 28℃; for 1h;
Stage #2: With sodium hydroxide In tetrahydrofuran; water for 8h; Reflux;
79.6%
Stage #1: N‑2‑[[2‑(dimethylamino)ethyl]methylamino]‑4‑methoxy‑5‑[[4‑(1‑methyl‑1H‑indole-3-yl)-2-pyrimidinyl]amino]aniline; 2-chloropropionyl chloride In water; acetone at -3 - 30℃; for 1.5h;
Stage #2: With triethylamine In water; acetone at 25 - 60℃;
77.14%
1421373-36-5

3-chloro-N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propanamide

1421373-65-0

[N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide]

Conditions
ConditionsYield
With triethylamine In acetonitrile at 80℃; for 6h;94%
With sodium hydroxide In tetrahydrofuran; water at 65℃; for 10h;94%
Stage #1: 3-chloro-N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propanamide With triethylamine In acetonitrile at 80℃; for 6h;
Stage #2: With water at 20℃; for 12h;
94%
1032452-86-0

2-chloro-4-(1'-methyl-1H-indol-3-yl)pyrimidine

5-(N-acrylamido)-4-((N,1-(2-(N,N-dimethylamino)ethyl)-N,1-methyl)amino)-2-methoxyaniline

1421373-65-0

[N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide]

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 2-methyl-propan-1-ol at 55℃; for 5h;93%
With toluene-4-sulfonic acid In butan-1-ol at 40℃; for 2.5h;92%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 7h; Reagent/catalyst; Time;75.5%
954421-16-0

(2E)-3-(dimethylamino)-1-(1-methyl-1H-indol-3-yl)-2-propen-1-one

N-[2-[2-dimethylaminoethylmethylamino]-4-methoxy-5-carboxamidinephenyl]prop-2-enamide

1421373-65-0

[N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide]

Conditions
ConditionsYield
With sodium hydroxide In butan-1-ol at 90 - 105℃;91%
1421372-67-9

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-2-nitrobenzene-1,4-diamine

79-10-7

acrylic acid

814-68-6

acryloyl chloride

1421373-65-0

[N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide]

Conditions
ConditionsYield
Stage #1: N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-2-nitrobenzene-1,4-diamine With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20 - 50℃;
Stage #2: acrylic acid; acryloyl chloride With N-ethyl-N,N-diisopropylamine at 20℃;
72.1%
2051-76-5

acrylic acid anhydride

1421372-66-8

N‑2‑[[2‑(dimethylamino)ethyl]methylamino]‑4‑methoxy‑5‑[[4‑(1‑methyl‑1H‑indole-3-yl)-2-pyrimidinyl]amino]aniline

1421373-65-0

[N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide]

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 5℃; for 2h;62%
1421372-67-9

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-2-nitrobenzene-1,4-diamine

79-10-7

acrylic acid

1421373-65-0

[N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide]

Conditions
ConditionsYield
Stage #1: N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-2-nitrobenzene-1,4-diamine With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran at 20℃; for 2h;
Stage #2: acrylic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine at 20℃; for 4h; Inert atmosphere;
61%
1075705-01-9

4-fluoro-2-methoxy-5-nitro-phenylamine

1421373-65-0

[N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}phenyl)propen-2-amide]

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: toluene-4-sulfonic acid / 2.5 h / 105 °C
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
3.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
4.1: N-ethyl-N,N-diisopropylamine / water; tetrahydrofuran / 0.25 h / 0 - 20 °C
4.2: 10 h / 65 °C
View Scheme
Multi-step reaction with 4 steps
1: toluene-4-sulfonic acid / 2.5 h / 105 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
3: iron; ammonium chloride / water; ethanol / 2 h / Reflux
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / Cooling with ice
View Scheme
Multi-step reaction with 5 steps
1: toluene-4-sulfonic acid / 2.5 h / 105 °C
2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
3: iron; ammonium chloride / water; ethanol / 2 h / Reflux
4: potassium carbonate / acetone / 0.5 h / -50 - -20 °C
5: triethylamine / acetonitrile / 6 h / 80 °C
View Scheme
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    Product Name AZD-9291 Synonyms AZD9291, >=98%;AZD9291 (free base);Osimertinib (AZD-9291);ZAD9291;AZD9291, Osimertinib;AZD9291 Base;Osimertinib Base;N-(2-{[2-(Dimethylamino)ethyl](methyl)amino}-4-meth

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    AZD-9291 CAS NO 1421373-65-0

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  • CAS 1421373-65-0 	AZD-9291

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    CAS 1421373-65-0 AZD-9291

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    Business Type:Lab/Research institutions

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    China (Mainland)  |  Contact Details

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    Osimertinib / Osimertinib Intermediate 4 / Azd-9291 CAS 1421373-65-0

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