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CAS No. : | 149520-94-5 | MDL No. : | MFCD09864446 |
Formula : | C6H9N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NGJGNTZJCFFZLK-UHFFFAOYSA-N |
M.W : | 155.15 | Pubchem ID : | 573233 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 39.08 |
TPSA : | 81.0 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.05 cm/s |
Log Po/w (iLOGP) : | 0.89 |
Log Po/w (XLOGP3) : | 0.27 |
Log Po/w (WLOGP) : | 0.18 |
Log Po/w (MLOGP) : | -0.58 |
Log Po/w (SILICOS-IT) : | 0.39 |
Consensus Log Po/w : | 0.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.11 |
Solubility : | 12.0 mg/ml ; 0.0775 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.53 |
Solubility : | 4.55 mg/ml ; 0.0294 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.34 |
Solubility : | 7.04 mg/ml ; 0.0454 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.96 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: at 75℃; Stage #2: With hydrazine hydrate In ethanol at 75℃; |
To a mixture of imidazo[l,2-a]pyrimidine-2-carboxylic acid ethyl ester and imidazo[l,2-a]pyrimidine-3-carboxylic acid ethyl ester (500 mg, 2.62 mmol, 1.0 eq) in EtOH ( 20 mL) was added hydrazine hydrate (180 mg, 2.88 mmol, 1.1 eq). The reaction mixture was heated at 75 °C overnight. The reaction mixture was concentrated and the resulting residue was purified by chromatography on a silica gel column (DCM/MeOH = 20/1, v/v) to give 2-amino-lH-imidazole-4-carboxylic acid ethyl ester (220 mg, 54percent) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrazine In ethanol at 75℃; for 16 h; | To a stirred solution of ethyl imidazo[l ,2-α]pyrimidine-2-carboxylate or ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (1 g, 5.2 mmol) in ethanol (40 mL) was added hydrazine monohydrate (0.28 mL, 5.7 mmol). The reaction was heated to 75 °C for 16 h and was concentrated under reduced pressure. The resulting light yellow solid was suspended in diethyl ether and filtered to collect ethyl 2-amino-1H-imidazole-4- carboxylate (800 mg, 100percent) as a white solid. [00243] 1E NMR (400 MHz, CD3OD) 5 7.27 (s, 1H), 4.24 (q, J= 7.0 Hz, 2H), 1.31(t, J= 7.0 Hz, 3H).[00244] 13C NMR (500 MHz, CD3OD) δ 165.5, 156.1, 131.8, 125.7, 63.8, 17.3.[00245] HPLC Phenomenex LUNA C- 18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 0.46 min, 100percent homogeneity index.[00246] Anal. Calcd for C6H9N3O2: C, 46.44; H, 5.84; N5 27.08. Found: C, 46.17;H, 5.65; N, 27.28.[00247] HRMS: Anal. Calcd. for C6Hi0N3O2 156.0773 found: 156.0779 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With hydrazine In ethanol at 75℃; for 16 h; | To a stirred solution of ethyl imidazo[l ,2-α]pyrimidine-2-carboxylate or ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (1 g, 5.2 mmol) in ethanol (40 mL) was added hydrazine monohydrate (0.28 mL, 5.7 mmol). The reaction was heated to 75 °C for 16 h and was concentrated under reduced pressure. The resulting light yellow solid was suspended in diethyl ether and filtered to collect ethyl 2-amino-1H-imidazole-4- carboxylate (800 mg, 100percent) as a white solid. [00243] 1E NMR (400 MHz, CD3OD) 5 7.27 (s, 1H), 4.24 (q, J= 7.0 Hz, 2H), 1.31(t, J= 7.0 Hz, 3H).[00244] 13C NMR (500 MHz, CD3OD) δ 165.5, 156.1, 131.8, 125.7, 63.8, 17.3.[00245] HPLC Phenomenex LUNA C- 18 4.6 x 50 mm, 0 to 100percent B over 4 minutes, 1 minutes hold time, A = 90percent water, 10percent methanol, 0.1percent TFA, B = 10percent water, 90percent methanol, 0.1percent TFA, RT = 0.46 min, 100percent homogeneity index.[00246] Anal. Calcd for C6H9N3O2: C, 46.44; H, 5.84; N5 27.08. Found: C, 46.17;H, 5.65; N, 27.28.[00247] HRMS: Anal. Calcd. for C6Hi0N3O2 156.0773 found: 156.0779 (M+H)+. |
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