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1421373-66-1
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Basic Information
CAS No.: 1421373-66-1
Name: AZD-9291 (Mesylate)
Article Data: 11
Molecular Structure:
Molecular Structure of 1421373-66-1 (AZD-9291 (Mesylate))
Formula: C29H37N7O5S
Molecular Weight: 595.723
Synonyms: AZD-9291 (Mesylate);N-[2-[[2-(Dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl]amino]phenyl]-2-propenamide methanesulfonate (1:1);AZD-9291 mesylate N-[2-[[2-(Dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1H-indol-3-yl)-2-pyrimidinyl]amino]phenyl]-2-propenamide methanesulfonate (1:1);Osimertinib mesylate;Mereletinib mesylate;Osimertinib;N-[2-(2-dimethylaminoethylmethylamino)-4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamide mesylate salt;Osimertinib Mesylate(AZD9291)
EINECS: 200-064-1
PSA: 153.79000
LogP: 5.81710
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Synthetic route
75-75-2

methanesulfonic 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]

1421373-66-1

N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate

Conditions
ConditionsYield
Stage #1: [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] With pyrographite In acetone at 25 - 55℃;
Stage #2: methanesulfonic acid at 25 - 55℃;		96.73%
With N-ethyl-N,N-diisopropylamine In ethanol; ethyl acetate at 70℃; for 1.5h;94%
In water; acetone at 50℃; for 1.5h; Inert atmosphere;94%
1075705-01-9

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

1421373-66-1

N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 5 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
5.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
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: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / Cooling with ice
5: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 6 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
6: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
1421372-66-8

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

1421373-66-1

N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-ethyl-N,N-diisopropylamine / water; tetrahydrofuran / 0.25 h / 0 - 20 °C
1.2: 10 h / 65 °C
2.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / Cooling with ice
2: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 0.5 h / -50 - -20 °C
2: triethylamine / acetonitrile / 6 h / 80 °C
3: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
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

1421373-66-1

N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
2.1: N-ethyl-N,N-diisopropylamine / water; tetrahydrofuran / 0.25 h / 0 - 20 °C
2.2: 10 h / 65 °C
3.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 3 steps
1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / Cooling with ice
3: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 4 steps
1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
2: potassium carbonate / acetone / 0.5 h / -50 - -20 °C
3: triethylamine / acetonitrile / 6 h / 80 °C
4: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
1421372-94-2

N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1-methyl-1H-indole-3-yl)-pyrimidine-2-amine

1421373-66-1

N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
2.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
3.1: N-ethyl-N,N-diisopropylamine / water; tetrahydrofuran / 0.25 h / 0 - 20 °C
3.2: 10 h / 65 °C
4.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
2: iron; ammonium chloride / water; ethanol / 2 h / Reflux
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / Cooling with ice
4: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 5 steps
1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
2: iron; ammonium chloride / water; ethanol / 2 h / Reflux
3: potassium carbonate / acetone / 0.5 h / -50 - -20 °C
4: triethylamine / acetonitrile / 6 h / 80 °C
5: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
1032452-86-0

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

1421373-66-1

N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 5 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
5.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
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: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / Cooling with ice
5: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 6 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
6: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
945016-63-7

3-(2-chloro-pyrimidin-4-yl)-1H-indole

1421373-66-1

N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
1.2: 3 h / 0 °C
2.1: toluene-4-sulfonic acid / 2.5 h / 105 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
4.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
5.1: N-ethyl-N,N-diisopropylamine / water; tetrahydrofuran / 0.25 h / 0 - 20 °C
5.2: 10 h / 65 °C
6.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
1.2: 3 h / 0 °C
2.1: toluene-4-sulfonic acid / 2.5 h / 105 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
4.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / Cooling with ice
6.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
1.2: 3 h / 0 °C
2.1: toluene-4-sulfonic acid / 2.5 h / 105 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
4.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
5.1: potassium carbonate / acetone / 0.5 h / -50 - -20 °C
6.1: triethylamine / acetonitrile / 6 h / 80 °C
7.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
1.2: 3 h / 0 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / 2.5 h / 105 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine / 2,2,2-trifluoroethanol / 1 h / 140 °C / Inert atmosphere
4.1: ammonium chloride; iron / ethanol; water / 2 h / 100 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
6.1: water; acetone / 1.5 h / 50 °C / Inert atmosphere
View Scheme
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

1421373-66-1

N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / acetonitrile / 6 h / 80 °C
2: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / tetrahydrofuran; water / 10 h / 65 °C
2: water; ethanol / 1.5 h / 70 °C
View Scheme
120-72-9

indole

1421373-66-1

N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: methylmagnesium bromide / diethyl ether; 1,2-dichloro-ethane / 0.42 h / 0 °C / Inert atmosphere
1.2: 16 h / 0 - 20 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
2.2: 3 h / 0 °C
3.1: toluene-4-sulfonic acid / 2.5 h / 105 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
5.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / Cooling with ice
7.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methylmagnesium bromide / diethyl ether; 1,2-dichloro-ethane / 0.42 h / 0 °C / Inert atmosphere
1.2: 16 h / 0 - 20 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
2.2: 3 h / 0 °C
3.1: toluene-4-sulfonic acid / 2.5 h / 105 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
5.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
6.1: N-ethyl-N,N-diisopropylamine / water; tetrahydrofuran / 0.25 h / 0 - 20 °C
6.2: 10 h / 65 °C
7.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 8 steps
1.1: methylmagnesium bromide / diethyl ether; 1,2-dichloro-ethane / 0.42 h / 0 °C / Inert atmosphere
1.2: 16 h / 0 - 20 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C
2.2: 3 h / 0 °C
3.1: toluene-4-sulfonic acid / 2.5 h / 105 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
5.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
6.1: potassium carbonate / acetone / 0.5 h / -50 - -20 °C
7.1: triethylamine / acetonitrile / 6 h / 80 °C
8.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methylmagnesium bromide / diethyl ether; 1,2-dichloro-ethane / 0.25 h / 0 °C / Inert atmosphere
1.2: 16 h / 0 °C / Inert atmosphere; Heating
2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
2.2: 3 h / 0 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / 2.5 h / 105 °C / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine / 2,2,2-trifluoroethanol / 1 h / 140 °C / Inert atmosphere
5.1: ammonium chloride; iron / ethanol; water / 2 h / 100 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
7.1: water; acetone / 1.5 h / 50 °C / Inert atmosphere
View Scheme
450-91-9

4-fluoro-2-methoxyaniline

1421373-66-1

N-(2-(N-(2-(dimethylamino)ethyl)-N-methylamino)-4-methoxy-5-((4-(1-methyl-1H-indole-3-yl)pyrimidine-2-yl)amino)phenyl)acrylamide methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sulfuric acid; potassium nitrate / 15 °C / Cooling with ice
2.1: toluene-4-sulfonic acid / 2.5 h / 105 °C
3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
4.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
5.1: N-ethyl-N,N-diisopropylamine / water; tetrahydrofuran / 0.25 h / 0 - 20 °C
5.2: 10 h / 65 °C
6.1: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 6 steps
1: sulfuric acid; potassium nitrate / 15 °C / Cooling with ice
2: toluene-4-sulfonic acid / 2.5 h / 105 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
4: iron; ammonium chloride / water; ethanol / 2 h / Reflux
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / Cooling with ice
6: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
Multi-step reaction with 7 steps
1: sulfuric acid; potassium nitrate / 15 °C / Cooling with ice
2: toluene-4-sulfonic acid / 2.5 h / 105 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 85 °C
4: iron; ammonium chloride / water; ethanol / 2 h / Reflux
5: potassium carbonate / acetone / 0.5 h / -50 - -20 °C
6: triethylamine / acetonitrile / 6 h / 80 °C
7: N-ethyl-N,N-diisopropylamine / ethyl acetate; ethanol / 1.5 h / 70 °C
View Scheme
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