4H-Pyrrolo [1,2-B] pyrazole -2-carboxylic acid , 5,6-dihydro -, Potassium Salt
- Product Name
- 4H-Pyrrolo [1,2-B] pyrazole -2-carboxylic acid , 5,6-dihydro -, Potassium Salt
- CAS No.
- 86477-09-0
- Chemical Name
- 4H-Pyrrolo [1,2-B] pyrazole -2-carboxylic acid , 5,6-dihydro -, Potassium Salt
- Synonyms
- Ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate;5,6-dihydro-4H-Pyrrolo[1,2-b]pyrazole-2-carboxylic acid ethyl ester;4H-Pyrrolo[1,2-b]pyrazole-2-carboxylic acid, 5,6-dihydro-, ethyl ester;4H-Pyrrolo [1,2-B] pyrazole -2-carboxylic acid , 5,6-dihydro -, Potassium Salt;4H-Pyrrolo [1,2-B] pyrazole -2-carboxylic acid , 5,6-dihydro -, Potassium Salt (1:1)
- CBNumber
- CB02510280
- Molecular Formula
- C9H12N2O2
- Formula Weight
- 180.2
- MOL File
- 86477-09-0.mol
4H-Pyrrolo [1,2-B] pyrazole -2-carboxylic acid , 5,6-dihydro -, Potassium Salt Property
- Melting point:
- 61-63 °C
- Boiling point:
- 320.0±30.0 °C(Predicted)
- Density
- 1.29±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- pka
- 0.56±0.20(Predicted)
- Appearance
- Light yellow to yellow Solid
- InChI
- InChI=1S/C9H12N2O2/c1-2-13-9(12)8-6-7-4-3-5-11(7)10-8/h6H,2-5H2,1H3
- InChIKey
- MGGGSJRWNQFCLE-UHFFFAOYSA-N
- SMILES
- N1=C(C(OCC)=O)C=C2CCCN12
Safety
- HS Code
- 2933998090
N-Bromosuccinimide Price
- Product number
- OR930225
- Product name
- Ethyl5,6-dihydro-4h-pyrrolo[1,2-b]pyrazole-2-carboxylate
- Purity
- 95%
- Packaging
- 250mg
- Price
- $254
- Updated
- 2021/12/16
- Product number
- OR930225
- Product name
- Ethyl5,6-dihydro-4h-pyrrolo[1,2-b]pyrazole-2-carboxylate
- Purity
- 95%
- Packaging
- 1g
- Price
- $573
- Updated
- 2021/12/16
- Product number
- 130078
- Product name
- 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylicacidethylester
- Purity
- 95%+
- Packaging
- 1g
- Price
- $990
- Updated
- 2021/12/16
- Product number
- CHM0118585
- Product name
- ETHYL 5,6-DIHYDRO-4H-PYRROLO[1,2-B]PYRAZOLE-2-CARBOXYLATE
- Purity
- 95.00%
- Packaging
- 500MG
- Price
- $1097.25
- Updated
- 2021/12/16
- Product number
- CHM0118585
- Product name
- ETHYL 5,6-DIHYDRO-4H-PYRROLO[1,2-B]PYRAZOLE-2-CARBOXYLATE
- Purity
- 95.00%
- Packaging
- 5G
- Price
- $3799.95
- Updated
- 2021/12/16
4H-Pyrrolo [1,2-B] pyrazole -2-carboxylic acid , 5,6-dihydro -, Potassium Salt Chemical Properties,Usage,Production
Synthesis
98262-66-9
623-47-2
86477-10-3
86477-09-0
A reaction was carried out with 3a,4,5,6-tetrahydro-3-oxo-3H-pyrrolo[1,2-c][1,2,3]oxadiazol-7-ium innerium salt (13.5 g, 0.107 mol, crude from Example 4) and ethyl propargylate (15.8 g, 16.3 ml, 0.16 mol) in anhydrous N,N-dimethylformamide (50 ml) under nitrogen The reaction was stirred under protection and heated to 120-122 °C for 12 hours. The course of the reaction was monitored by HPLC (using a Prodigy ODS3 4.6×150 mm column with 90:10 to 10:90 water/acetonitrile containing 0.02% trifluoroacetic acid as the mobile phase in a gradient elution for 10 min). Under these conditions, the retention time of ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate (the more polar target isomer) was 2.6-2.7 min, whereas the retention time of ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate (the less polar non-target isomer) was 2.8-2.9 min. The UV detector was set at 215 nm because the absorption difference between the two isomers is significant at 254 nm and the non-target isomer is almost undetectable. After completion of the reaction, the mixture was concentrated to a dark syrupy consistency using an oil pump vacuum at a bath temperature not exceeding 50 °C. The ratio of the two esters in the dark syrup was 2.13:1 in favor of the target product ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate as determined by NMR. The dark syrup was diluted with toluene and up-sampled by washing with hexane to a silica gel column (500 mL) preloaded in hexane. The column was eluted first with hexane-ethyl acetate (4:1) followed by hexane-ethyl acetate (1:1). The elution process was monitored by HPLC (conditions as above). Fractions containing both esters were collected and separated again by column chromatography. Fractions containing only ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate were combined and concentrated to give 11 g (57%) of the pure product in white crystalline form with a melting point of 35-37 °C. Similarly, 6.5 g (33.7%) of ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate was obtained as white crystals with a melting point of 205 °C.
References
[1] Patent: US2004/242874, 2004, A1. Location in patent: Page 13-14
[2] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1991, vol. 30, # 2, p. 169 - 175
[3] Patent: US2004/242874, 2004, A1. Location in patent: Page 12-13
[4] Patent: US2004/242874, 2004, A1. Location in patent: Page 13
[5] Organic Process Research and Development, 2006, vol. 10, # 4, p. 712 - 716
4H-Pyrrolo [1,2-B] pyrazole -2-carboxylic acid , 5,6-dihydro -, Potassium Salt Preparation Products And Raw materials
Raw materials
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