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pd_meltingpoint:52-53 °C
Purity:99%
InChI:InChI=1/C7H9ClN2O/c8-4-7(11)10-3-1-2-6(10)5-9/h6H,1-4H2/t6-/m0/s1
A four-step synthesis of the main impuri...
Novel piperazine-derived conformationall...
An efficient and high-yielding synthetic...
The invention discloses a preparation me...
The present invention relates to process...
and Alkali metal bromides are in vildagl...
chloroacetyl chloride
L-prolinamide
(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile
| Conditions | Yield |
|---|---|
|
chloroacetyl chloride; L-prolinamide;
With
potassium carbonate;
In
acetonitrile;
at 0 - 15 ℃;
With
trifluoroacetic anhydride;
at 0 - 15 ℃;
|
92% |
|
chloroacetyl chloride; L-prolinamide;
With
potassium carbonate;
In
acetonitrile;
at 0 - 20 ℃;
With
trifluoroacetic anhydride;
at 0 - 25 ℃;
|
92% |
|
chloroacetyl chloride; L-prolinamide;
With
trifluoroacetyl chloride;
In
N,N-dimethyl-formamide;
at 50 ℃;
for 1.5h;
With
trifluoroacetyl chloride;
In
N,N-dimethyl-formamide;
at 60 ℃;
for 1.5h;
Reagent/catalyst;
Temperature;
|
83.4% |
|
chloroacetyl chloride; L-prolinamide;
In
Isopropyl acetate; N,N-dimethyl-formamide;
at 15 - 35 ℃;
for 2h;
With
1,3,5-trichloro-2,4,6-triazine;
In
Isopropyl acetate; N,N-dimethyl-formamide;
at 25 - 35 ℃;
for 0.75h;
|
66% |
|
chloroacetyl chloride; L-prolinamide;
In
dichloromethane;
at 20 ℃;
for 3h;
Inert atmosphere;
With
2,6-dimethylpyridine;
In
dichloromethane;
at 20 ℃;
for 1h;
Inert atmosphere;
With
trichlorophosphate;
In
dichloromethane;
at 5 - 20 ℃;
for 17h;
Inert atmosphere;
|
56% |
|
With
potassium carbonate; trifluoroacetic anhydride;
In
tetrahydrofuran; ethyl acetate;
|
|
|
chloroacetyl chloride; L-prolinamide;
In
dichloromethane;
at 25 - 30 ℃;
With
2,6-dimethylpyridine;
In
dichloromethane;
for 0.25h;
With
trichlorophosphate;
In
dichloromethane;
at 5 - 20 ℃;
Reagent/catalyst;
Time;
Temperature;
|
5.2 g |
|
chloroacetyl chloride; L-prolinamide;
With
triethylamine;
In
N,N-dimethyl-formamide;
at 0 ℃;
for 1h;
With
1,3,5-trichloro-2,4,6-triazine;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 0.833333h;
|
(S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid
(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile
| Conditions | Yield |
|---|---|
|
(S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid;
With
4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; ammonium bicarbonate;
In
acetonitrile;
at 20 ℃;
for 4.5h;
With
1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide;
at 40 ℃;
for 4h;
|
70% |
|
With
sulfuric acid; acetonitrile;
at 95 ℃;
for 5.5h;
Temperature;
Time;
|
39% |
|
Multi-step reaction with 2 steps
1.1: dicyclohexyl-carbodiimide / dichloromethane / 1 h / 0 - 30 °C
1.2: 3 h / 25 - 30 °C
2.1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
With
oxalyl dichloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide;
In
dichloromethane;
|
|
|
Multi-step reaction with 2 steps
1.1: 1,3,5-trichloro-2,4,6-triazine / dichloromethane / 3 h / 0 °C / Reflux
1.2: 2 h
2.1: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 4 h / 35 - 48 °C
With
1,3,5-trichloro-2,4,6-triazine;
In
dichloromethane; N,N-dimethyl-formamide;
|
|
|
Multi-step reaction with 2 steps
1: di-tert-butyl dicarbonate; ammonium bicarbonate; pyridine / acetonitrile / 1.5 h / 20 °C / Inert atmosphere
2: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C
With
pyridine; 1,3,5-trichloro-2,4,6-triazine; di-tert-butyl dicarbonate; ammonium bicarbonate;
In
N,N-dimethyl-formamide; acetonitrile;
|
|
|
Multi-step reaction with 2 steps
1: ammonium bicarbonate; pyridine; di-tert-butyl dicarbonate / acetonitrile / 1.5 h / 25 °C
2: 1,3,5-trichloro-2,4,6-triazine / N,N-dimethyl-formamide / 4 h / 40 °C
With
pyridine; 1,3,5-trichloro-2,4,6-triazine; di-tert-butyl dicarbonate; ammonium bicarbonate;
In
N,N-dimethyl-formamide; acetonitrile;
|
|
|
Multi-step reaction with 2 steps
1.1: dicyclohexyl-carbodiimide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
1.2: 7 h / 20 °C / Inert atmosphere
2.1: trifluoroacetic anhydride / tetrahydrofuran / 7 h / 0 - 20 °C / Inert atmosphere
With
dicyclohexyl-carbodiimide; trifluoroacetic anhydride;
In
tetrahydrofuran; dichloromethane;
|
|
|
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide / dichloromethane / 1.5 h
2: trichlorophosphate / N,N-dimethyl-formamide / 2 h / 0 - 5 °C
With
dicyclohexyl-carbodiimide; trichlorophosphate;
In
dichloromethane; N,N-dimethyl-formamide;
|
|
|
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate; sodium iodide / acetonitrile / 6 h / 85 °C
2: ammonium bicarbonate / acetonitrile / 12 h / 85 °C
3: trichlorophosphate / N,N-dimethyl-formamide / 3 h / 0 °C / Heating
With
sodium hydrogencarbonate; ammonium bicarbonate; sodium iodide; trichlorophosphate;
In
N,N-dimethyl-formamide; acetonitrile;
|
(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide
L-prolinamide
L-proline
L-proline
vildagliptin
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