N-Methyl-1-iMidazolecarboxaMide synthesis
- Product Name:N-Methyl-1-iMidazolecarboxaMide
- CAS Number:72002-25-6
- Molecular formula:C5H7N3O
- Molecular Weight:125.13
593-51-1
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Yield: 100%
Reaction Conditions:
in N,N-dimethyl-formamide;acetonitrile at 20; for 2 h;
Steps:
1.1g General Procedure 1g: [056] 1-[3-[1,3-Benzodioxol-5-yl(methyl)carbamoyl]phenyl]- N-methyl-3-(trifluoromethyl)-6,7-dihydro-4H-pyrazolo[4,3-c] pyridine-5-carboxamide:
General procedure: To a solution of 1,1'- carbonyldiimidazole (53 mg, 0.296 mmol) in DMF/CH3CN (1:3, 1 ml) at rt, methylamine hydrochloride (20 mg, 0.326 mmol) was added. The mixture was allowed to stir for 2h at rt. Then, the reaction was evaporated to yield N-methylimidazole-1- carboxamide quantitatively. To a solution of [002] (131.7 mg, 0.296 mmol) in DCM (1.2 ml) at 0°C, triethylamine (1.66 mL, 1.18 mmol) was added followed by N-methylimidazole-1-carboxamide. The reaction was allowed to stir for 12h at rt. Then, the reaction was extracted with water, the organic phase was dried over Na2SO4 and concentrated under vacuum. The title compound was obtained after purification by silica gel flash-column chromatography with 60% AcOEt in cyclohexane as eluent, as a white solid in 67% yield (99.5 mg).1H NMR (400 MHz, DMSO- d6) δ 7.57 - 7.32 (m, 4H), 6.98 (d, J = 2.1Hz, 1H), 6.78 (d, J = 8.2 Hz, 1H), 6.74 - 6.60 (m, 2H), 6.02 (s, 2H), 4.47 (s, 2H), 3.59 (t, J = 5.6 Hz, 2H), 3.33 (s, 3H), 2.62 (d, J = 4.2 Hz, 3H), 2.60 - 2.54 (m, 2H); UPLC-MS: tR = 1.93 min (generic method); MS (ESI) m/z calcd for C24H23F3N5O4 (M+H)+: 502.5, found: 502.6.
References:
FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA;ISTITUTO GIANNINA GASLINI;FONDAZIONE PER LA RICERCA SULLA FIBROSI CISTICA - ONLUS;BANDIERA, Tiziano;BERTOZZI, Fabio;DI FRUSCIA, Paolo;SORANA, Federico;BERTI, Francesco;RODRIGUEZ GIMENO, Alejandra;CACI, Emanuela;FERRERA, Loretta;PEDEMONTE, Nicoletta;VICENTE GALIETTA, Luis Juan WO2018/167690, 2018, A1 Location in patent:Page/Page column 62-63
530-62-1
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74-89-5
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72002-25-6
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506-59-2
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530-62-1
936 suppliers
$6.00/25g
72002-25-6
70 suppliers
$25.00/250mg