Pyridine → N-((4S)-2-amino-7'-methoxyspiro[1,3-oxazole-4,9'-xanthen]-2'-yl)-5-chloro-2-pyridinecarboxamide

반응식

[N:1]([C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([O:18][CH3:19])=[CH:11][CH:12]=3)[C@:7]3([CH2:23][O:22][C:21]([NH2:24])=[N:20]3)[C:6]=2[CH:5]=1)=[N+]=[N-].[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.FC(F)(F)C(O[C:36](=[O:41])C(F)(F)F)=O.[Cl:44]CCl>>[NH2:24][C:21]1[O:22][CH2:23][C@:7]2([N:20]=1)[C:6]1[CH:5]=[C:4]([NH:1][C:36]([C:26]3[CH:27]=[CH:28][C:29]([Cl:44])=[CH:30][N:25]=3)=[O:41])[CH:17]=[CH:16][C:15]=1[O:14][C:13]1[C:8]2=[CH:9][C:10]([O:18][CH3:19])=[CH:11][CH:12]=1

참가 물질

반응물 4

HCID 1049Pyridine

HCID 6344Dichloromethane

HCID 9845Trifluoroacetic anhydride

HCID 86640718(S)-2'-azido-7'-methoxy-5H-spiro[oxazole-4,9'-xanthen]-2-amine

생성물 1

HCID 59272386N-((4S)-2-amino-7'-methoxyspiro[1,3-oxazole-4,9'-xanthen]-2'-yl)-5-chloro-2-pyridinecarboxamide

실험 절차

A solution of (S)-2′-azido-7′-methoxy-5H-spiro[oxazole-4,9′-xanthen]-2-amine (1.162 g, 3.59 mmol) in dichloromethane (25 mL) was treated with pyridine (0.775 mL, 9.50 mmol) followed by trifluoroaceticacid anhydride (0.9 mL, 6.43 mmol) at RT. The reaction was allowed to stir for 2 hours during which formation of desired product was detected (M+H˜420) along with traces of unreacted starting material. The reaction was allowed to stir for another 6 hours and diluted with DCM (75 mL), water (20 mL), and separated the organic layer. The organic layer was dried over anhydrous sodium sulfate, and concentrated to yield (S)—N-(2′-azido-7′-methoxy-5H-spiro[oxazole-4,9′-xanthene]-2-yl)-2,2,2-trifluoroacetamide as a yellowish solid. MS (ESI pos. ion) m/z: 420 (M+1).