| Identification | Back Directory | [Name]
ETHYL 2-AMINO-1H-PYRROLE-3-CARBOXYLATE | [CAS]
108290-86-4 | [Synonyms]
SKL228
ETHYL 2-AMINO-1H-PYRROLE-...
Ethyl 2-Aminopyrrole-3-carboxylate
ETHYL 2-AMINO-1H-PYRROLE-3-CARBOXYLATE
2-amino-1H-Pyrrole-3-carboxy-lic acid ethyl ester
1H-Pyrrole-3-carboxylicacid, 2-aMino-, ethyl ester | [Molecular Formula]
C7H10N2O2 | [MDL Number]
MFCD09953569 | [MOL File]
108290-86-4.mol | [Molecular Weight]
154.17 |
| Chemical Properties | Back Directory | [Boiling point ]
360.5±22.0 °C(Predicted) | [density ]
1.238±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C, protect from light | [pka]
18.24±0.50(Predicted) | [Appearance]
Light green to green Solid | [InChI]
InChI=1S/C7H10N2O2/c1-2-11-7(10)5-3-4-9-6(5)8/h3-4,9H,2,8H2,1H3 | [InChIKey]
XKJUSNOUOLSNJN-UHFFFAOYSA-N | [SMILES]
N1C=CC(C(OCC)=O)=C1N | [CAS DataBase Reference]
108290-86-4 |
| Hazard Information | Back Directory | [Uses]
2-Amino-1H-Pyrrole-3-carboxylic acid ethyl ester acts as a reagent in the synthesis of pyrrolo pyrimidines which functions as glucocerebrosidase activators use in treatment of medical disorders. | [Synthesis]
1. Preparation of ethyl 2-amino-1H-pyrrole-3-carboxylate. Ethyl 3-amino-3-iminopropionate (390 mg, 3.0 mmol) was dissolved in ethyl acetate (20 mL) under argon protection with vigorous stirring. Anhydrous chloroacetaldehyde was added rapidly at 22 °C. The reaction mixture was stirred for 10 minutes and then heated to reflux for 20 minutes. Cool to room temperature and filter through a silica gel column (15 g). The residue in the reaction flask was washed several times with ethyl acetate (20 mL x 5) and the filtrates were combined. The filtrate was concentrated under reduced pressure to give 120 mg of light yellow solid product in 47% yield. The product was characterized as follows: 1H NMR (500 MHz, CDCl3) δ (ppm): 7.92 (br, 1H), 6.28 (t, J = 2.8 Hz, 1H), 6.15 (dd, J = 2.0 Hz, 1H), 4.94 (br, 2H), 4.24 (q, J = 7.1 Hz, 2H), 1.33 (t, J = 7.1 Hz, 3H).13C NMR (125 MHz, CDCl3) δ (ppm): 166.5, 145.4, 110.3, 107.5, 94.5, 59.3, 14.7. | [References]
[1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 5, p. 1555 - 1560
[2] Patent: WO2017/4408, 2017, A1. Location in patent: Paragraph 0087; 0089; 0090
[3] Patent: WO2016/73891, 2016, A1. Location in patent: Paragraph 00204
[4] Patent: US9447100, 2016, B2. Location in patent: Page/Page column 556; 557 |
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