2-Chloroquinoline → 4-(2-((Quinolin-2-yloxy)methyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

반응식

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([CH2:16][OH:17])[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.[H-].[Na+].Cl[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1>C1COCC1>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[O:17][CH2:16][C:14]1[N:15]=[C:8]2[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[N:12][CH:11]=[CH:10][N:9]2[CH:13]=1

참가 물질

실험 절차

A mixture of compound 1d (5.0 g, 21 mmol) and NaH (2.5 g, 64 mmol) in anhydrous THF (300 mL) was stirred at rt for 10 min. 2-Chloroquinoline (4.2 g, 25 mmol) was then added and the mixture was heated to 70° C. for 5 h. The reaction was quenched with brine (300 mL) and extracted with EtOAc (2×500 mL). The organic layer was washed with brine (300 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue obtained was recrystallized with hot EtOAc-hexanes to give compound 31a. Mass Spectrum (LCMS, ESI pos.): Calcd. for C20H19N5O2: 362.1 (M+H). found: 362.2.