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1297537-33-7

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CAS No.: 1297537-33-7
Name: 5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide
Article Data: 9
Molecular Structure:
Molecular Structure of 1297537-33-7 (5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide)
Formula: N/A
Molecular Weight: 396.836
Synonyms: 5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide
Density: 1.41±0.1 g/cm3(Predicted)
Melting Point: 210 - 212?C
Boiling Point: 714.7±60.0 °C(Predicted)
Related products
Synthetic route

3-acetyl-1H-pyrazole-5-carboxylic acid

1297537-41-7

(S)-4-(1-(2-aminopropyl) 1H-pyrazol-3-yl)-2-chlorobenzonitrile

1297537-33-7

5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 10 - 20℃; Inert atmosphere;87.5%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;79.5%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;
1297537-41-7

(S)-4-(1-(2-aminopropyl) 1H-pyrazol-3-yl)-2-chlorobenzonitrile

C6H5ClN2O2

1297537-33-7

5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 3h;87.1%
1297537-37-1

2-chloro-4- (1H-pyrazol-3-yl)benzonitrile

1297537-33-7

5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triphenylphosphine / ethyl acetate / 0.25 h / Inert atmosphere
1.2: 20 °C
2.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride; diisopropyl (E)-azodicarboxylate; triphenylphosphine / n-heptane; dichloromethane; water; ethyl acetate
2: water
View Scheme
Multi-step reaction with 2 steps
1: triphenylphosphine; hydrogenchloride; di-isopropyl azodicarboxylate / ethyl acetate / 10 - 20 °C / Inert atmosphere
2: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 10 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere
1.2: 24 h / 20 °C
2.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere
View Scheme

3-acetyl-1H-pyrazole-5-carboxylic acid

1297537-41-7

(S)-4-(1-(2-aminopropyl) 1H-pyrazol-3-yl)-2-chlorobenzonitrile

96042-30-7

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

67-63-0

isopropyl alcohol

1297537-33-7

5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
In water
...Expand
1297537-39-3

2-Chloro-4-(1H-pyrazol-5-yl)benzonitrile hydrochloride

1297537-33-7

5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanol; water
2: hydrogenchloride; diisopropyl (E)-azodicarboxylate; triphenylphosphine / n-heptane; dichloromethane; water; ethyl acetate
3: water
View Scheme
154607-01-9

4-bromo-2-chlorobenzonitrile

1297537-33-7

5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetonitrile; water / 0.5 h / Inert atmosphere; Reflux
1.2: 2.5 h / 60 - 70 °C / Inert atmosphere
2.1: hydrogenchloride / water / 2 h / 10 °C
2.2: 4 h / 0 - 5 °C
3.1: triphenylphosphine; hydrogenchloride; di-isopropyl azodicarboxylate / ethyl acetate / 10 - 20 °C / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 10 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate / water; tetrahydrofuran / 40 °C
2.1: hydrogenchloride / ethanol / Reflux
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere
3.2: 24 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere
View Scheme
1297537-35-9

2-Chloro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)benzonitrile

1297537-33-7

5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / water / 2 h / 10 °C
1.2: 4 h / 0 - 5 °C
2.1: triphenylphosphine; hydrogenchloride; di-isopropyl azodicarboxylate / ethyl acetate / 10 - 20 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 10 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride / ethanol / Reflux
2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere
2.2: 24 h / 20 °C
3.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride / water; methanol / 2 h / 10 °C
2.1: triphenylphosphine / ethyl acetate / Inert atmosphere
2.2: 10 - 20 °C / Inert atmosphere
2.3: 30 - 45 °C / Inert atmosphere
3.1: potassium tert-butylate / toluene / 1 h / 0 °C / Inert atmosphere
3.2: 2 h / 0 - 20 °C / Inert atmosphere
View Scheme

(S)-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propyl-2-yl)amino tert-butyl ester

1297537-33-7

5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride / water; 1,4-dioxane / 3 h / 10 °C
2.1: potassium tert-butylate / toluene / 1 h / 0 °C / Inert atmosphere
2.2: 2 h / 0 - 20 °C / Inert atmosphere
View Scheme
37622-89-2

5-acetyl-1H-pyrazole-3-carboxylic acid ethyl ester

1297537-41-7

(S)-4-(1-(2-aminopropyl) 1H-pyrazol-3-yl)-2-chlorobenzonitrile

1297537-33-7

5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
Stage #1: (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile With potassium tert-butylate In toluene at 0℃; for 1h; Inert atmosphere;
Stage #2: 5-acetyl-1H-pyrazole-3-carboxylic acid ethyl ester In toluene at 0 - 20℃; for 2h; Inert atmosphere;		15.4 g
548797-51-9

2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

1297537-33-7

5-acetyl-N-{(2S)-1-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetonitrile; water / 0.5 h / Inert atmosphere; Reflux
1.2: palladium catalyst / 2 h / 60 - 70 °C / Inert atmosphere
2.1: hydrogenchloride / water; methanol / 2 h / 10 °C
3.1: triphenylphosphine / ethyl acetate / Inert atmosphere
3.2: 10 - 20 °C / Inert atmosphere
3.3: 30 - 45 °C / Inert atmosphere
4.1: potassium tert-butylate / toluene / 1 h / 0 °C / Inert atmosphere
4.2: 2 h / 0 - 20 °C / Inert atmosphere
View Scheme
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