Pyridine → N-((4S)-2-amino-7'-methoxyspiro[1,3-oxazole-4,9'-xanthen]-2'-yl)-5-chloro-2-pyridinecarboxamide
Reaction equation
[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]=1Participants
Procedure
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).
Sources & evidence
- ORD record
- ord-ee56e5ba881b451ebadd60d1c4413429
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426447B2
Reaction notes
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