| Identification | Back Directory | [Name]
Pyrrolo[3,4-c]pyrazole-5(1H)-carboxylic acid, 4,6-dihydro-, 1,1-dimethylethyl ester | [CAS]
657428-42-7 | [Synonyms]
EOS-60428
N-Boc-pyrazolopyrrolidine
5-Boc-4,6-Dihydro-1H-pyrr...
5-Boc-4,6-Dihydro-1H-pyrrolo[3,4-c]pyrazole
tert-butyl pyrrolo[3,4-c]pyrazole-5(1H,4H,6H)-carboxylate
tert-butyl 1H,4H,5H,6H-pyrrolo[3,4-c]pyrazole-5-
carboxylate
tert-butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate
tert-Butyl 4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylate
4,6-Dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylic acid tert-butyl ester
Pyrrolo[3,4-c]pyrazole-5(1H)-carboxylic acid, 4,6-dihydro-, 1,1-dimethylethyl ester | [Molecular Formula]
C10H15N3O2 | [MDL Number]
MFCD08061257 | [MOL File]
657428-42-7.mol | [Molecular Weight]
209.24 |
| Chemical Properties | Back Directory | [Boiling point ]
366.0±42.0 °C(Predicted) | [density ]
1.243±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [pka]
15.04±0.20(Predicted) | [Appearance]
Light yellow to yellow Solid | [InChI]
InChI=1S/C10H15N3O2/c1-10(2,3)15-9(14)13-5-7-4-11-12-8(7)6-13/h4H,5-6H2,1-3H3,(H,11,12) | [InChIKey]
IBUNCTVDGYIKAP-UHFFFAOYSA-N | [SMILES]
N1=CC2CN(C(OC(C)(C)C)=O)CC=2N1 |
| Hazard Information | Back Directory | [Uses]
4,6-Dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic Acid tert-Butyl Ester is an intermediate in the synthesis of Omarigliptin (O633100), a potent and selective dipeptidyl peptidase 4 (DPP-4) inhibitor to be used as treatment for type 2 diabetes. | [Synthesis]
Tert-butyl 3-((dimethylamino)methylene)-4-oxopyrrolidine-1-carboxylate (1 g, 4.16 mmol, 1.00 eq.) was used as a raw material and dissolved in ethanol (10 mL) with hydrazine hydrate (340 mg, 6.79 mmol, 1.63 eq.). The mixed solution was stirred and reacted at room temperature for 5 hours. Upon completion of the reaction, the solvent was removed by vacuum concentration and the crude product obtained was purified by silica gel column chromatography with ethyl acetate/petroleum ether as eluent (the ratio was gradually adjusted from 1:5 to 1:2). Finally, 250 mg (29% yield) of tert-butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate was obtained and the product was a yellow oil. The product was confirmed by LC/MS (Method C, ESI) analysis: retention time RT = 1.30 min, mass-to-charge ratio m/z ~ 210.0 [M + H]+. | [References]
[1] Patent: WO2013/127267, 2013, A1. Location in patent: Page/Page column 97; 98
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 19, p. 5361 - 5366
[3] Patent: EP3144310, 2017, A1 |
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