تفاعل #559072

معادلة التفاعل

trans-2-Methyl-pyrimidine-4-carboxylic acid [2-(3,5-difluorophenyl)-9-hydroxy-1-oxo-2-aza-spiro[4.5]dec-7-yl]-amide

DAST

→

title compound

trans-2-Methyl-pyrimidine-4-carboxylic acid [2-(3,5-difluoro-phenyl)-9-fluoro-1-oxo-2-aza-spiro[4.5]dec-7-yl]-amide

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىquenched with saturated aqueous NaHCO3
2. 2
   استخلاصThe aqueous layer was extracted with DCM
3. 3
   غسيلThe combined organic layers were washed with brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىThe residue was chromatographed on silica gel (0 to 70% EtOAc in hexanes)

الإجراء التجريبي

To a solution of trans-2-Methyl-pyrimidine-4-carboxylic acid [2-(3,5-difluorophenyl)-9-hydroxy-1-oxo-2-aza-spiro[4.5]dec-7-yl]-amide (crude, <0.121 mmol) in DCM (5 mL) was added DAST (20.3 μL, 0.154 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight and quenched with saturated aqueous NaHCO3. The aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica gel (0 to 70% EtOAc in hexanes) to give 2 mg of the title compound, trans-2-methyl-pyrimidine-4-carboxylic acid [2-(3,5-difluoro-phenyl)-9-fluoro-1-oxo-2-aza-spiro[4.5]dec-7-yl]-amide. 1H NMR (400 MHz, CDCl3) δ 8.79 (d, J=5.0 Hz, 1H), 8.00 (d, J=8.5 Hz, 1H), 7.82 (t, J=5.0 Hz, 1H), 7.26-7.21 (m, 1H), 6.54 (tt, J=8.8, 2.2 Hz, 1H), 5.22-5.05 (m, 1H), 4.55-4.43 (m, 1H), 3.79-3.66 (m, 2H), 2.71 (s, 3H), 2.45-2.25 (m, 3H), 2.09-1.92 (m, 3H), 1.74-1.54 (m, 2H). ESI-MS m/z: 419 (M+H)+.

المصدر